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Bioorganic Chemistry pp 97–194Cite as

Enzymatic C-C bond formation in asymmetric synthesis

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Part of the book series: Topics in Current Chemistry ((4143,volume 184))

Abstract

Catalytic aldol reactions are among the most useful synthetic methods with a high potential for convergent asymmetric synthesis. As an increasing number of lyases is becoming available for preparative applications, in this review the state of the art concerning the application of these biocatalysts for enzymatic C-C bond formations is evaluated. The scope, and the individual limitations, of the most important types of enzyme-catalyzed transformations are discussed against a more recent mechanistic and protein-structural background. Special emphasis is placed on the synthetic power of a stereodivergent building-block approach which is facilitated by the prevalence of families of stereocomplementary enzymes which often have a very similar, broad substrate tolerance. The methodology is highlighted by exemplary applications to the synthesis of valuable polyfunctionalized products which otherwise are difficult to prepare and to handle by classical chemical methods.

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9 References

  1. Testa B, Trager WF (1990) Chirality 2: 129

    Google Scholar 

  2. Wainer IW, Drayer DE (1988) Drug Stereochemistry. Marcel Dekker, New York

    Google Scholar 

  3. Ariens EJ, van Rensen JJS, Welling W (1988) Stereoselectivity of Pesticides. Elsevier, Amsterdam

    Google Scholar 

  4. Whitesides GM, Wong C-H (1985) Angew Chem Int Ed Engl 24: 617

    Google Scholar 

  5. Jones JB (1986) Tetrahedron 42: 3351

    Google Scholar 

  6. Davies HG, Green RH, Kelly DR, Roberts SM (1989) Biotransformations in Preparative Organic Chemistry. Academic Press, London

    Google Scholar 

  7. Crout DHG, Christen M (1989) Biotransformations in Organic Synthesis. In: Scheffold R (ed) Modern Synthetic Methods. Springer, Berlin Heidelberg, New York, vol. 5, p 1

    Google Scholar 

  8. Gerhartz W (1991) Enzymes in Industry: Production and Applications. VCH, Weinheim

    Google Scholar 

  9. Boland W, Froessl C, Lorenz M (1991) Synthesis 12: 1049

    Google Scholar 

  10. Schellenberger V, Jakubke HD (1991) Angew Chem Int Ed Engl 30: 1437

    Google Scholar 

  11. Holland HL (1992) Organic Synthesis with Oxidative Enzymes. VCH, Weinheim

    Google Scholar 

  12. David S, Augé C, Gautheron C (1991) Adv Carbohydr Chem Biochem 49: 175

    Google Scholar 

  13. Blanch HW, Clark DS (1991) Applied Biocatalysis, vol 1. Marcel Dekker, New York

    Google Scholar 

  14. Drauz K, Waldmann H (1995) Enzyme Catalysis in Organic Synthesis. A Comprehensive Handbook. VCH, Weinheim

    Google Scholar 

  15. Rozzell D, Wagner F (1992) Biocatalytic Production of Amino Acids & Derivatives. Hanser, Munich

    Google Scholar 

  16. Wong C-H, Whitesides GM (1994) Enzymes in Synthetic Organic Chemistry. Pergamon, Oxford

    Google Scholar 

  17. Faber K (1995) Biotransformations in Organic Chemistry, 2nd edn. Springer, Berlin

    Google Scholar 

  18. Servi S (1992) Microbial Reagents in Organic Synthesis, vol 381. Kluwer Academic, Dordrecht

    Google Scholar 

  19. Halgas J (1992) Biocatalysts in Organic Synthesis. Elsevier, Amsterdam

    Google Scholar 

  20. Poppe L, Novák L (1992) Selective Biocatalysis. A Synthetic Approach. VCH, Weinheim

    Google Scholar 

  21. Toone EJ, Simon ES, Bednarski MD, Whitesides GM (1989) Tetrahedron 45: 5365

    Google Scholar 

  22. Azerad R (1995) Bull Soc Chim Fr 132: 17

    Google Scholar 

  23. Santaniello E, Ferraboschi P, Grisenti P, Manzocchi A (1992) Chem Rev 92: 1071

    Google Scholar 

  24. Waldmann H, Sebastian D (1994) Chem Rev 94: 911

    Google Scholar 

  25. David S, Auge C, Gautheron C (1992) Adv Carbohydr Chem Biochem 49: 175

    Google Scholar 

  26. Varki A (1994) Proc Natl Acad Sci USA 91: 7390

    Google Scholar 

  27. Carlos TM, Harlan JM (1994) Blood 84: 2068

    Google Scholar 

  28. Hynes RO, Lander AD (1992) Cell 68: 303

    Google Scholar 

  29. Wegner CD (1994) Adhesion Molecules. Academic Press, London

    Google Scholar 

  30. Chibata I (1978) Immobilized Enzymes. Research and Development. Wiley, New York

    Google Scholar 

  31. Trevan MD (1980) Immobilized Enzymes. An Introduction and Applications in Biotechnology. Wiley, New York

    Google Scholar 

  32. Mosbach K (1976) Methods Enzymol 44, (1987) 135, (1987) 136, (1988) 137

    Google Scholar 

  33. Woodley JM (1992) Immobilized Biocatalysts. In: Smith K (ed) Solids Supports and Catalysts in Organic Synthesis. Ellis Horwood, Chichester, p 254

    Google Scholar 

  34. Chenault HK, Whitesides GM (1987) Appl Biochem Biotechnol 14: 147

    Google Scholar 

  35. Chenault HK, Simon ES, Whitesides GM (1988) Biotechnol Genet Eng Rev 6: 221

    Google Scholar 

  36. Schreiber SL, Verdine GL (1991) Tetrahedron 47: 2543

    Google Scholar 

  37. Hedstrom L (1994) Curr Opin Struct Biol 4: 608

    Google Scholar 

  38. Janda KD (1994) Proc Natl Acad Sci USA 91: 10779

    Google Scholar 

  39. Gordon EM, Barrett RW, Dower WJ, Fodor SPA, Gallop MA (1994) J Med Chem 37: 1385

    Google Scholar 

  40. Gallop MA, Barrett RW, Dower WJ, Fodor SPA, Gordon EM (1994) J Med Chem 37: 1233

    Google Scholar 

  41. Kluger R (1990) Chem Rev 90: 1151

    Google Scholar 

  42. Schomburg D, Salzmann M (1990–1995) Enzyme Handbook. Springer, Berlin

    Google Scholar 

  43. Horecker BL, Tsolas O, Lai CY (1972) Aldolases. In: Boyer PD (ed) The Enzymes. 3 edn. Academic Press, New York, vol. VII, p 213

    Google Scholar 

  44. Trombetta G, Balboni G, di Iasio A, Grazi E (1977) Biochem Biophys Res Commun 74: 1297

    Google Scholar 

  45. Kuo DJ, Rose IA (1985) Biochemistry 24: 3947

    Google Scholar 

  46. Grazi E, Cheng T, Horecker BL (1962) Biochem Biophys Res Commun 7: 250

    Google Scholar 

  47. Kadonaga JT, Knowles JR (1983) Biochemistry 22: 130

    Google Scholar 

  48. Webb EC (1992) Enzyme Nomenclature. Academic Press, San Diego

    Google Scholar 

  49. Demerec M, Adelberg EA, Clark AJ, Hartman PE (1966) Genetics 54: 61

    Google Scholar 

  50. Smith HO, Nathans D (1973) J Mol Biol 81: 419

    Google Scholar 

  51. Kluger R (1990) Chem Rev 90: 1151

    Google Scholar 

  52. Littlechild JA, Watson HC (1993) Trends Biochem Sci 18: 36

    Google Scholar 

  53. Morris AJ, Tolan DR (1993) J Biol Chem 268: 1095

    Google Scholar 

  54. Morris AJ, Tolan DR (1994) Biochemistry 33: 12291

    Google Scholar 

  55. Pollak A, Blumenfeld H, Wax M, Baughn RL, Whitesides GM (1980) J Am Chem Soc 102: 6324

    Google Scholar 

  56. Bossow B, Berke W, Wandrey C (1992) BioEngineering 8: 12

    Google Scholar 

  57. Sobolov SB, Bartoszkomalik A, Oeschger TR, Montelbano MM (1994) Tetrahedron Lett 35: 7751

    Google Scholar 

  58. Goße C, Fessner W-D, unpublished

    Google Scholar 

  59. Kragl U, Gödde A, Wandrey C, Lubin N, Augé C (1994) J Chem Soc Perkin Trans I 119

    Google Scholar 

  60. Kragl U, Gygax D, Ghisalba O, Wandrey C (1991) Angew Chem Int Ed Engl 30: 827

    Google Scholar 

  61. Kragl U, Niedermeyer U, Kula M-R, Wandrey C (1990) Ann N Y Acad Sci 613: 617

    Google Scholar 

  62. Raetz CRH, Dowhan W (1990) J Biol Chem 265: 1235

    Google Scholar 

  63. Unger FM (1981) Adv Carbohydr Chem Biochem 38: 323

    Google Scholar 

  64. Varki A (1993) Glycobiology 3: 97

    Google Scholar 

  65. Schauer R, Wember M, Wirtz-Peitz F, Ferreira do Amaral C (1971) Hoppe Seyler's Z Physiol Chem 352: 1073

    Google Scholar 

  66. Comb DG, Roseman S (1960) J Biol Chem 235: 2529

    Google Scholar 

  67. Deijl CM, Vliegenthart JFG (1983) Biochem Biophys Res Commun 111: 668

    Google Scholar 

  68. Baumann W, Freidenreich J, Weisshaar G, Brossmer R, Friebolin H (1989) Biol Chem Hoppe Seyler 370: 141

    Google Scholar 

  69. Uchida Y, Tsukada Y, Sugimori T (1984) J Biochem 96: 507

    Google Scholar 

  70. Ohta Y, Shimosaka M, Murata K, Tsukada Y, Kimura A (1986) Appl Microbiol Biotechnol 24: 386

    Google Scholar 

  71. Aisaka K, Tamura S, Arai Y, Uwajima T (1987) Biotechnol Lett 9: 633

    Google Scholar 

  72. Ohta Y, Tsukada Y, Sugimori T, Murata K, Kimura A (1989) Agric Biol Chem 53: 477

    Google Scholar 

  73. Aisaka K, Igarashi A, Yamaguchi K, Uwajima T (1991) Biochem J 276: 541

    Google Scholar 

  74. Izard T, Lawrence MC, Malby RL, Lilley GG, Colman PM (1994) Structure 2: 361

    Google Scholar 

  75. Schauer R, Stoll S, Zbiral E, Schreiner E, Brandstetter HH, Vasella A, Baumberger F (1987) Glycoconjugate J 4: 361

    Google Scholar 

  76. Kraulis PJ (1991) J Appl Crystallogr 24: 946

    Google Scholar 

  77. Kim MJ, Hennen WJ, Sweers HM, Wong C-H (1988) J Am Chem Soc 110: 6481

    Google Scholar 

  78. Harlan JM, Liu DY (1992) Adhesion — Its Role in Inflammatory Disease. W.H. Freeman and Co, New York

    Google Scholar 

  79. Kelm S, Schauer R, Manuguerra JC, Gross HJ, Crocker PR (1994) Glycoconjugate J 11: 576

    Google Scholar 

  80. Troy FA (1992) Glycobiology 2: 5

    Google Scholar 

  81. Wiley DC, Skehel JJ (1987) Annu Rev Biochem 56: 365

    Google Scholar 

  82. Augé C, David S, Gautheron C, Malleron A, Cavayé B (1988) New J Chem 12: 733

    Google Scholar 

  83. Simon ES, Bednarski MD, Whitesides GM (1988) J Am Chem Soc 110: 7159

    Google Scholar 

  84. Lin CH, Sugai T, Halcomb RL, Ichikawa Y, Wong C-H (1992) J Am Chem Soc 114: 10138

    Google Scholar 

  85. Ichikawa Y, Liu JLC, Shen GJ, Wong C-H (1991) J Am Chem Soc 113: 6300

    Google Scholar 

  86. Blayer S, Woodley JM, Dawson MJ, Lilly MD (1995) Process Development for Scale-Up of Biotransformations: Chemoenzymatic Synthesis of N-Acetylneuraminic Acid. Biotrans 95, Warwick, UK

    Google Scholar 

  87. Liu JLC, Shen GJ, Ichikawa Y, Rutan JF, Zapata G, Vann WF, Wong C-H (1992) J Am Chem Soc 114: 3901

    Google Scholar 

  88. Augé C, Gautheron C, David S, Malleron A, Cavayé B, Bouxom B (1990) Tetrahedron 46: 201

    Google Scholar 

  89. Koppert K, Brossmer R (1992) Tetrahedron Lett 33: 8031

    Google Scholar 

  90. Sparks MA, Williams KW, Lukacs C, Schrell A, Priebe G, Spaltenstein A, Whitesides GM (1993) Tetrahedron 49: 1

    Google Scholar 

  91. Zhou PZ, Salleh HM, Honek JF (1993) J Org Chem 58: 264

    Google Scholar 

  92. Fitz W, Wong C-H (1994) J Org Chem 59: 8279

    Google Scholar 

  93. Gross HJ, Brossmer R (1988) Eur J Biochem 177: 583

    Google Scholar 

  94. Brossmer R, Gross HJ (1994) Methods Enzymol 247: 177

    Google Scholar 

  95. Brossmer R, Gross HJ (1994) Methods Enzymol 247: 153

    Google Scholar 

  96. Jacob GS, Kirmaier C, Abbas SZ, Howard SC, Steininger CN, Welply JK, Scudder P (1995) Biochemistry 34: 1210

    Google Scholar 

  97. Varki A (1992) Glycobiology 2: 25

    Google Scholar 

  98. Halcomb RL, Fitz W, Wong C-H (1994) Tetrahedron Asymmetry 5: 2437

    Google Scholar 

  99. Kong DCM, von Itzstein M (1995) Tetrahedron Lett 36: 957

    Google Scholar 

  100. Isecke R, Brossmer R (1994) Tetrahedron 50: 7445

    Google Scholar 

  101. Schrell A, Whitesides GM (1990) Liebigs Ann Chem 1111

    Google Scholar 

  102. Kragl U, Gödde A, Wandrey C, Kinzy W, Cappon JJ, Lugtenburg J (1993) Tetrahedron Asymmetry 4: 1193

    Google Scholar 

  103. Augé C, Bouxom B, Cavayé B, Gautheron C (1989) Tetrahedron Lett 30: 2217

    Google Scholar 

  104. David S, Malleron A, Cavayé B (1992) New J Chem 16: 751

    Google Scholar 

  105. Gautheron LNC, Ichikawa Y, Wong C-H (1991) J Am Chem Soc 113: 7816

    Google Scholar 

  106. Ladisch S, Hasegawa A, Li RX, Kiso M (1995) Biochemistry 34: 1197

    Google Scholar 

  107. Knappmann BR, Kula MR (1990) Appl Microbiol Biotechnol 33: 324

    Google Scholar 

  108. Ghalambor MA, Heath EC (1966) J Biol Chem 241: 3222

    Google Scholar 

  109. Sugai T, Shen GJ, Ichikawa Y, Wong C-H (1993) J Am Chem Soc 115: 413

    Google Scholar 

  110. Hammond SM, Claesson A, Jansson AM, Larsson L-G, Pring BG, Town CM, Ekström B (1987) Nature 327: 730

    Google Scholar 

  111. Claesson A (1987) J Org Chem 52: 4414

    Google Scholar 

  112. Wood WA (1972) 2-Keto-3-deoxy-6-phosphogluconic and Related Aldolases. In: Boyer PD (ed) The Enzymes, 3rd ed. Academic, New York, vol. 7, p 281

    Google Scholar 

  113. Scopes RK (1984) Anal Biochem 136: 525

    Google Scholar 

  114. Shelton MC, Toone EJ (1995) Tetrahedron Asymmetry 6: 207

    Google Scholar 

  115. Knappmann BR, Elnawawy MA, Schlegel HG, Kula MR (Erratum (1995) Carbohydr Res 272: C1)

    Google Scholar 

  116. Egan SE, Fliege R, Tong S, Shibata A, Wolf RE, Conway T (1992) J Bacteriol 174: 4638

    Google Scholar 

  117. Carter AT, Pearson BM, Dickinson JR, Lancashire WE (1993) Gene 130: 155

    Google Scholar 

  118. Conway T, Yi KC, Egan SE, Wolf REJ, Rowley DL (1991) J Bacteriol 173: 5247

    Google Scholar 

  119. Conway T, Fliege R, Jones-Kilpatrick D, Liu J, Barnell WO, Egan SE (1991) Mol Microbiol 5: 2901

    Google Scholar 

  120. Hugouvieux-Cotte-Pattat N, Robert-Baudouy J (1994) Mol Microbiol 11: 67

    Google Scholar 

  121. Suzuki N, Wood WA (1980) J Biol Chem 255: 3427

    Google Scholar 

  122. Hammerstedt RH, Möhler H, Decker KA, Ersfeld D, Wood WA (1975) Methods Enzymol 42: 258

    Google Scholar 

  123. Mavridis IM, Hatada MH, Tulinsky A, Lebioda L (1982) J Mol Biol 162: 419

    Google Scholar 

  124. Dekker EE, Kitson RP (1992) J Biol Chem 267: 10507

    Google Scholar 

  125. Dekker EE, Kobes RD, Grady SR (1975) Methods Enzymol 42: 280

    Google Scholar 

  126. Dekker EE, Nishihara H, Grady SR (1975) Methods Enzymol 42: 285

    Google Scholar 

  127. Kuratomi K, Fukunaga K (1963) Biochim Biophys Acta 78: 617

    Google Scholar 

  128. Maitra U, Dekker EE (1964) J Biol Chem 239: 1485

    Google Scholar 

  129. Rosso RG, Adams E (1967) J Biol Chem 242: 5524

    Google Scholar 

  130. Vlahos CJ, Dekker EE (1988) J Biol Chem 263: 11683

    Google Scholar 

  131. Patil RV, Dekker EE (1992) J Bacteriol 174: 102

    Google Scholar 

  132. Taha TSM, Deits TL (1994) Biochem Biophys Res Commun 200: 459

    Google Scholar 

  133. Meloche HP, Mehler L (1973) J Biol Chem 248: 6333

    Google Scholar 

  134. Meloche HP, Monti CT (1975) J Biol Chem 250: 6875

    Google Scholar 

  135. Scholtz JM, Schuster SM (1984) Bioorg Chem 12: 229

    Google Scholar 

  136. Floyd NC, Liebster MH, Turner NJ (1992) J Chem Soc Perkin Trans I 1085

    Google Scholar 

  137. Allen ST, Heintzelman GR, Toone EJ (1992) J Org Chem 57: 426

    Google Scholar 

  138. Nishihara H, Dekker EE (1972) J Biol Chem 247: 5079

    Google Scholar 

  139. Meloche HP, O'Connell EL (1982) Methods Enzymol 90: 263

    Google Scholar 

  140. Dahms AS, Anderson RL (1972) J Biol Chem 247: 2238

    Google Scholar 

  141. Anderson RL, Dahms AS (1975) Methods Enzymol 42: 269

    Google Scholar 

  142. Dahms AS (1974) Biochem Biophys Res Commun 60: 1433

    Google Scholar 

  143. Dahms AS, Donald A (1982) Methods Enzymol 90: 269

    Google Scholar 

  144. Augé C, Delest V (1993) Tetrahedron Asymmetry 4: 1165

    Google Scholar 

  145. Elshafei AM, Abdel-Fatah OM (1989) Enzyme Microb Technol 11: 367

    Google Scholar 

  146. Elshafei AM, Mohawed SM, Ammar MS, Abdel-Fatah OM (1995) Int J Gen Mol Microbiol 67: 211

    Google Scholar 

  147. Auge C, Delest V (1995) Tetrahedron Asymmetry 6: 863

    Google Scholar 

  148. Fish DC, Blumenthal HJ (1966) Methods Enzymol 9: 529

    Google Scholar 

  149. Hirschbein BL, Mazenod FP, Whitesides GM (1982) J Org Chem 47: 3765

    Google Scholar 

  150. Simon ES, Grabowski S, Whitesides GM (1989) J Am Chem Soc 111: 8920

    Google Scholar 

  151. Blacklow RS, Warren L (1962) J Biol Chem 237: 3520

    Google Scholar 

  152. Annunziato PW, Wright LF, Vann WF, Silver RP (1995) J Bacteriol 177: 312

    Google Scholar 

  153. Ganguli S, Zapata G, Wallis T, Reid C, Boulnois G, Vann WF, Roberts IS (1994) J Bacteriol 176: 4583

    Google Scholar 

  154. Edwards U, Müller A, Hammerschmidt S, Gerardy-Schahn R, Frosch M (1994) Mol Microbiol 14: 141

    Google Scholar 

  155. Brossmer R, Rose U, Kasper D, Smith TL, Grasmuk H, Unger FM (1980) Biochem Biophys Res Commun 96: 1282

    Google Scholar 

  156. Raetz CRH (1993) J Bacteriol 175: 5745

    Google Scholar 

  157. Doong RL, Ahmad S, Jensen RA (1991) Plant Cell Environ 14: 113

    Google Scholar 

  158. Levin DH, Racker E (1959) J Biol Chem 234: 2532

    Google Scholar 

  159. Woisetschläger M, Högenauer G (1987) MGG Mol Gen Genet 207: 369

    Google Scholar 

  160. Woisetschläger M, Högenauer G (1986) J Bacteriol 168: 437

    Google Scholar 

  161. Dotson GD, Dua RK, Clemens JC, Wooten EW, Woodard RW (1995) J Biol Chem 270: 13698

    Google Scholar 

  162. Ray PH (1980) J Bacteriol 141: 635

    Google Scholar 

  163. Ray PH (1982) Method Enzymol 83: 525

    Google Scholar 

  164. Baasov T, Sheffer-Dee-Noor S, Kohen A, Jakob A, Belakhov V (1993) Eur J Biochem 217: 991

    Google Scholar 

  165. Yanase H, Okuda M, Kita K, Shibata K, Sakai Y, Kato Y (1995) Appl Microbiol Biotechnol 43: 228

    Google Scholar 

  166. Bednarski MD, Crans DC, DiCosimo R, Simon ES, Stein PD, Whitesides GM, Schneider MJ (1988) Tetrahedron Lett 29: 427

    Google Scholar 

  167. Wong C-H, Drueckhammer DG, Durrwachter JR, Lacher B, Chauvet CJ, Wang YF, Sweers HM, Smith GL, Yang LJS, Hennen WJ (1989) Enzyme-catalyzed synthesis of carbohydrates. In: Horton D, Hawkins LD, McGarvey GJ (eds) Trends in Synthetic Carbohydrate Chemistry. American Chemical Society, Washington, vol. 386, p 317

    Google Scholar 

  168. Doong RL, Jensen RA (1992) New Phytol 121: 165

    Google Scholar 

  169. Srinivasan PR, Sprinson DB (1959) J Biol Chem 234: 716

    Google Scholar 

  170. Hurwitz J, Weissbach A (1959) J Biol Chem 234: 710

    Google Scholar 

  171. Zurawski G, Brown KD, Killingly D, Yanofsky C (1978) Proc Natl Acad Sci USA 75: 4271

    Google Scholar 

  172. Shultz J, Hermodson MA, Garner CC, Herrmann KM (1984) J Biol Chem 259: 9655

    Google Scholar 

  173. Ray JM, Yanofsky C, Baeuerle R (1988) J Bacteriol 170: 5500

    Google Scholar 

  174. Weaver LM, Herrmann KM (1990) J Bacteriol 172: 6581

    Google Scholar 

  175. Sprinson DB, Srinivasan PR, Katagiri M (1962) Methods Enzymol 5: 394

    Google Scholar 

  176. Schoner R, Herrmann KM (1976) J Biol Chem 251: 5440

    Google Scholar 

  177. Paravicini G, Schmidheini T, Braus G (1989) Eur J Biochem 186: 361

    Google Scholar 

  178. Ray JM, Bauerle R (1991) J Bacteriol 173: 1894

    Google Scholar 

  179. Stuart F, Hunter IS (1993) Biochim Biophys Acta 1161: 209

    Google Scholar 

  180. Muday GK, Herrmann KM (1990) J Bacteriol 172: 2259

    Google Scholar 

  181. Dyer WE, Weaver LM, Zhao J, Kuhn DN, Weller SC, Herrmann KM (1990) J Biol Chem 265: 1608

    Google Scholar 

  182. Weaver LM, Pinto JEBP, Herrmann KM (1993) Bioorg Med Chem Lett 3: 1421

    Google Scholar 

  183. Doong RL, Gander JE, Ganson RJ, Jensen RA (1992) Physiol Plant 84: 351

    Google Scholar 

  184. Reimer LM, Conley DL, Pompliano DL, Frost JW (1986) J Am Chem Soc 108: 8010

    Google Scholar 

  185. Montchamp J-L, Piehler LT, Frost JW (1992) J Am Chem Soc 114: 4453

    Google Scholar 

  186. Draths KM, Frost JW (1990) J Am Chem Soc 112: 1657

    Google Scholar 

  187. Draths KM, Ward TL, Frost JW (1992) J Am Chem Soc 114: 9725

    Google Scholar 

  188. Draths KM, Frost JW (1995) J Am Chem Soc 117: 2395

    Google Scholar 

  189. Fessner W-D (1992) A Building Block Strategy for Asymmetric Synthesis: The DHAP Aldolases. In: Servi S (ed) Microbial Reagents in Organic Synthesis. Kluwer Academic, Dordrecht, vol. 381, p 43

    Google Scholar 

  190. Fessner W-D (1993) GIT Fachz Lab 37: 951

    Google Scholar 

  191. Lebherz HG (1972) Biochemistry 11: 2243

    Google Scholar 

  192. Lebherz HG, Rutter WJ (1969) Biochemistry 8: 109

    Google Scholar 

  193. Harris CE, Kobes RD, Teller DC, Rutter WJ (1969) Biochemistry 8: 2442

    Google Scholar 

  194. Schwartz NB, Abram D, Feingold DS (1974) Biochemistry 13: 1726

    Google Scholar 

  195. Fessner W-D, Sinerius G, Schneider A, Dreyer M, Schulz GE, Badia J, Aguilar J (1991) Angew Chem Int Ed Engl 30: 555

    Google Scholar 

  196. Taylor JF, Green AA, Cori GT (1948) J Biol Chem 173: 591

    Google Scholar 

  197. Vanderheiden BS, Meinhart JO, Dodson RG, Krebs EG (1962) J Biol Chem 237: 2095

    Google Scholar 

  198. Richards OC, Rutter WJ (1961) J Biol Chem 236: 3177

    Google Scholar 

  199. Periana RA, Motiu-DeGrood R, Chiang Y, Hupe DJ (1980) J Am Chem Soc 102: 3923

    Google Scholar 

  200. Fessner W-D, Sinerius G (1994) Angew Chem Int Ed Engl 33: 209

    Google Scholar 

  201. Stribling D (1974) Biochem J 141: 725

    Google Scholar 

  202. Bednarski MD, Simon ES, Bischofberger N, Fessner W-D, Kim MJ, Lees W, Saito T, Waldmann H, Whitesides GM (1989) J Am Chem Soc 111: 627

    Google Scholar 

  203. Whitesides GM, personal communication

    Google Scholar 

  204. Paterson MC, Norton IL, Hartman FC (1972) Biochemistry 11: 2070

    Google Scholar 

  205. Magnien A, Le Clef B, Biellmann JF (1984) Biochemistry 23: 6858

    Google Scholar 

  206. Weis K, Fessner W-D, unpublished

    Google Scholar 

  207. Eyrisch O, Fessner W-D (1995) Angew Chem Int Ed Engl 34: 1639

    Google Scholar 

  208. Fessner W-D, Sinerius G (1994) Bioorg Med Chem 2: 639

    Google Scholar 

  209. von der Osten CH, Sinskey AJ, Barbas CF, Pederson RL, Wang YF, Wong C-H (1989) J Am Chem Soc 111: 3924

    Google Scholar 

  210. Götz F, Fischer S, Schleifer K-H (1980) Eur J Biochem 108: 295

    Google Scholar 

  211. Dreyer MK, Schulz GE (1993) J Mol Biol 231: 549

    Google Scholar 

  212. Sinerius G, Schneider A, Goße C, Fessner W-D, unpublished

    Google Scholar 

  213. Rutter WJ, Richards OC, Woodfin BM (1961) J Biol Chem 236: 3193

    Google Scholar 

  214. Spolter PD, Adelman RC, Weinhouse S (1965) J Biol Chem 240: 1327

    Google Scholar 

  215. Berthiaume L, Tolan DR, Sygusch J (1993) J Biol Chem 268: 10826

    Google Scholar 

  216. Berthiaume L, Loisel TP, Sygusch J (1991) J Biol Chem 266: 17099

    Google Scholar 

  217. Richard JP (1984) J Am Chem Soc 106: 4926

    Google Scholar 

  218. Richard JP (1993) Biochem Soc Trans 21: 549

    Google Scholar 

  219. Phillips SA, Thornalley PJ (1993) Eur J Biochem 212: 101

    Google Scholar 

  220. Sinerius G (1994) Ph.D. thesis, University of Freiburg

    Google Scholar 

  221. Waagen V, Barua TK, Anthonsen HW, Hansen LK, Fossli DJ, Hough E, Anthonsen T (1994) Tetrahedron 50: 10055

    Google Scholar 

  222. Effenberger F, Straub A (1987) Tetrahedron Lett 28: 1641

    Google Scholar 

  223. Pederson RL, Esker J, Wong C-H (1991) Tetrahedron 47: 2643

    Google Scholar 

  224. Colbran RL, Jones JKN, Matheson NK, Rozema I (1967) Carbohydr Res 4: 355

    Google Scholar 

  225. Jung SH, Jeong JH, Miller P, Wong C-H (1994) J Org Chem 59: 7182

    Google Scholar 

  226. Crans DC, Whitesides GM (1985) J Am Chem Soc 107: 7019

    Google Scholar 

  227. Crans DC, Kazlauskas RJ, Hirschbein BL, Wong C-H, Abril O, Whitesides GM (1987) Methods Enzymol 136: 263

    Google Scholar 

  228. Meyerhof O, Lohmann K, Schuster P (1936) Biochem Zeitschr 286: 301

    Google Scholar 

  229. Willnow P (1984) Fructose-1,6-bisphosphate Aldolase. In: Bergmeyer H-J (ed) Methods of Enzymatic Analysis. 3rd edn. Verlag Chemie, Weinheim, vol. 4, p 346

    Google Scholar 

  230. Fessner W-D, Walter C (1992) Angew Chem Int Ed Engl 31: 614

    Google Scholar 

  231. Colombo G, Tate PW, Girotti AW, Kemp RG (1975) J Biol Chem 250: 9404

    Google Scholar 

  232. Babul J (1978) J Biol Chem 253: 4350

    Google Scholar 

  233. Eyrisch O, Sinerius G, Fessner W-D (1993) Carbohydr Res 238: 287

    Google Scholar 

  234. Walter C (1996) Ph.D. thesis, RWTH Aachen

    Google Scholar 

  235. Liu KKC, Pederson RL, Wong C-H (1991) J Chem Soc, Perkin Trans 1: 2669

    Google Scholar 

  236. Kajimoto T, Liu KKC, Pederson RL, Zhong Z, Ichikawa Y, Porco JAJ, Wong C-H (1991) J Am Chem Soc 113: 6187

    Google Scholar 

  237. Kajimoto T, Chen L, Liu KKC, Wong C-H (1991) J Am Chem Soc 113: 6678

    Google Scholar 

  238. Esders TW, Michrina CA (1979) J Biol Chem 254: 2710

    Google Scholar 

  239. Arth H-L, Sinerius G, Fessner W-D (1995) Liebigs Ann Chem 2037

    Google Scholar 

  240. Drueckhammer DG, Durrwachter JR, Pederson RL, Crans DC, Daniels L, Wong C-H (1989) J Org Chem 54: 70

    Google Scholar 

  241. Gresser MJ, Tracey AS (1990) Vanadates as Phosphate Analogs in Biochemistry. In: Chasteen ND (ed) Vanadium in Biological Systems. Physiology and Biochemistry. Kluwer Academic, Dordrecht, p 63

    Google Scholar 

  242. Nour-Eldeen AF, Craig MM, Gresser MJ (1985) J Biol Chem 260: 6836

    Google Scholar 

  243. Crans DC, Schelble SM, Theisen LA (1991) J Org Chem 56: 1266

    Google Scholar 

  244. London J (1974) J Biol Chem 249: 7977

    Google Scholar 

  245. Sugimoto S, Nosoh Y (1971) Biochim Biophys Acta 235: 210

    Google Scholar 

  246. Freeze H, Brock TD (1970) J Bacteriol 101: 541

    Google Scholar 

  247. Ingram JM, Hochster RM (1967) Can J Biochem 45: 929

    Google Scholar 

  248. Stribling D, Perham RN (1973) Biochem J 131: 833

    Google Scholar 

  249. Barnes EM, Akagi JM, Himes RH (1971) Biochim Biophys Acta 227: 199

    Google Scholar 

  250. Krishnan G, Altekar W (1991) Eur J Biochem 195: 343

    Google Scholar 

  251. Baldwin SA, Perham RN (1978) Biochem J 169: 643

    Google Scholar 

  252. Brockamp HP, Kula MR (1990) Appl Microbiol Biotechnol 34: 287

    Google Scholar 

  253. Lebherz HG, Rutter WJ (1973) J Biol Chem 248: 1650

    Google Scholar 

  254. Bai NJ, Pai MR, Murthy PS, Venkitasubramanian TA (1975) Arch Biochem Biophys 168: 235

    Google Scholar 

  255. Schnarrenberger C, Pelzer-Reith B, Yatsuki H, Freund S, Jacobshagen S, Hori K (1994) Arch Biochem Biophys 313: 173

    Google Scholar 

  256. Russell GK, Gibbs M (1967) Biochim Biophys Acta 132: 145

    Google Scholar 

  257. Willard J, Gibbs M (1968) Biochim Biophys Acta 151: 438

    Google Scholar 

  258. Fluri R, Ramasarma T, Horecker BL (1967) Eur J Biochem 1: 117

    Google Scholar 

  259. Krüger I, Schnarrenberger C (1983) Eur J Biochem 136: 101

    Google Scholar 

  260. Lebherz HG, Leadbetter MM, Bradshaw RA (1984) J Biol Chem 259: 1011

    Google Scholar 

  261. Heil JA, Lebherz HG (1978) J Biol Chem 253: 6599

    Google Scholar 

  262. Valentin ML, Bolte J (1993) Tetrahedron Lett 34: 8103

    Google Scholar 

  263. Fernández-Sousa J, Gavilanes FG, Gavilanes JG, Paredes JA (1978) Arch Biochem Biophys 188: 456

    Google Scholar 

  264. Brenner-Holzach O (1979) Arch Biochem Biophys 194: 321

    Google Scholar 

  265. Kochman M, Kwiatkowska D (1972) Arch Biochem Biophys 152: 856

    Google Scholar 

  266. Certa U, Ghersa P, Döbeli H, Matile H, Kocher HP, Shrivastava IK, Shaw AR, Perrin LH (1988) Science 240: 1036

    Google Scholar 

  267. Ting S-M, Sia CL, Lai CY, Horecker BL (1971) Arch Biochem Biophys 144: 485

    Google Scholar 

  268. Komatsu SK, Feeney R (1970) Biochim Biophys Acta 206: 305

    Google Scholar 

  269. Yeltman DR, Harris BG (1977) Biochim Biophys Acta 484: 188

    Google Scholar 

  270. Rajkumar TV, Woodfin BM, Rutter WJ (1966) Methods Enzym 9: 491

    Google Scholar 

  271. Marquardt RR (1971) Can J Biochem 49: 658

    Google Scholar 

  272. Peanasky RJ, Lardy HA (1990) J Biol Chem 265: 1608

    Google Scholar 

  273. Gracy RW, Lacko AG, Horecker BL (1969) J Biol Chem 244: 3913

    Google Scholar 

  274. Penhoet EE, Kochman M, Rutter WJ (1969) Biochemisty 8: 4391

    Google Scholar 

  275. Izzo P, Costanzo P, Lupo A, Rippa E, Paolella G, Salvatore F (1988) Eur J Biochem 174: 569

    Google Scholar 

  276. von der Osten CH, Barbas CF, Wong C-H, Sinskey AJ (1989) Mol Microbiol 3: 1625

    Google Scholar 

  277. Schwelberger HG, Kohlwein SD, Paltauf F (1989) Eur J Biochem 180: 301

    Google Scholar 

  278. Mutoh N, Hayashi Y (1994) Biochim Biophys Acta 1183: 550

    Google Scholar 

  279. Berthiaume L, Beaudry D, Lazure C, Tolan DR, Sygusch J (1989) Arch Biochem Biophys 272: 281

    Google Scholar 

  280. Alefounder PR, Baldwin SA, Perham RN, Short NJ (1989) Biochem J 257: 529

    Google Scholar 

  281. Sygusch J, Beaudry D, Allaire M (1987) Proc Natl Acad Sci USA 84: 7846

    Google Scholar 

  282. Gamblin SJ, Davies GJ, Grimes JM, Jackson RM, Littlechild JA, Watson HC (1991) J Mol Biol 219: 573

    Google Scholar 

  283. Gamblin SJ, Cooper B, Millar JR, Davies GJ, Littlechild JA, Watson HC (1990) FEBS Lett 262: 282

    Google Scholar 

  284. Hester G, Brenner-Holzach O, Rossi FA, Struck-Donatz M, Winterhalter KH, Smit JDG, Piontek K (1991) FEBS Lett 292: 237

    PubMed  Google Scholar 

  285. Brockamp HP, Kula MR (1990) Tetrahedron Lett 31: 7123

    Google Scholar 

  286. Walter C, Petersen M, Fessner W-D, unpublished

    Google Scholar 

  287. Wong C-H, Whitesides GM (1983) J Org Chem 48: 3199

    Google Scholar 

  288. Schmid W, Whitesides GM (1990) J Am Chem Soc 112: 9670

    Google Scholar 

  289. Schmid W, Heidlas J, Mathias JP, Whitesides GM (1992) Liebigs Ann Chem 95

    Google Scholar 

  290. Borysenko CW, Spaltenstein A, Straub JA, Whitesides GM (1980) J Am Chem Soc 111: 9275

    Google Scholar 

  291. Wong C-H, Mazenod FP, Whitesides GM (1983) J Org Chem 48: 3493

    Google Scholar 

  292. Durrwachter JR, Sweers HM, Nozaki K, Wong C-H (1986) Tetrahedron Lett 27: 1261

    Google Scholar 

  293. Peters J, Brockamp HP, Minuth T, Grothus M, Steigel A, Kula MR, Elling L (1993) Tetrahedron Asymmetry 4: 1173

    Google Scholar 

  294. Durrwachter JR, Wong C-H (1988) J Org Chem 53: 4175

    Google Scholar 

  295. Schneider A (1990) Diploma thesis, University of Freiburg

    Google Scholar 

  296. Jaeschke G, Goße C, Petersen M, Fessner W-D, unpublished

    Google Scholar 

  297. Bednarski MD, Waldmann HJ, Whitesides GM (1986) Tetrahedron Lett 27: 5807

    Google Scholar 

  298. Fessner W-D, Sinerius G, Schneider A, Weis K (1991) Limits of Aldolase Stereoselectivity. 4th Chemical Congress of North America and 202nd ACS National Meeting, New York, BIOL 9

    Google Scholar 

  299. Lees WJ, Whitesides GM (1993) J Org Chem 58: 1887

    Google Scholar 

  300. Straub A, Effenberger F, Fischer P (1990) J Org Chem 55: 3926

    Google Scholar 

  301. Fessner W-D, unpublished

    Google Scholar 

  302. Angyal SJ (1969) Angew Chem Int Ed Engl 8: 157

    Google Scholar 

  303. Jones JKN, Sephton HH (1960) Can J Chem 38: 753

    Google Scholar 

  304. Kapuscinski M, Franke FP, Flanigan I, MacLeod JK, Williams JF (1985) Carbohydr Res 140: 69

    Google Scholar 

  305. Paoletti F, Williams JF, Horecker BL (1979) Arch Biochem Biophys 198: 614

    Google Scholar 

  306. Durrwachter JR, Drueckhammer DG, Nozaki K, Sweers HM, Wong C-H (1986) J Am Chem Soc 108: 7812

    Google Scholar 

  307. Turner NJ, Whitesides GM (1989) J Am Chem Soc 111: 624

    Google Scholar 

  308. Liu KKC, Wong C-H (1992) J Org Chem 57: 4789

    Google Scholar 

  309. Maliakel BP, Schmid W (1993) J Carbohydr Chem 12: 415

    Google Scholar 

  310. Nicotra F, Panza L, Russo G, Verani A (1993) Tetrahedron Asymmetry 4: 1203

    Google Scholar 

  311. Matsumoto K, Shimagaki M, Nakata T, Oishi T (1993) Tetrahedron Lett 34: 4935

    Google Scholar 

  312. Shimagaki M, Muneshima H, Kubota M, Oishi T (1993) Chem Pharm Bull 41: 282

    Google Scholar 

  313. Schultz M, Waldmann H, Kunz H, Vogt W (1990) Liebigs Ann Chem 1019

    Google Scholar 

  314. Myles DC, Andrulis PJI, Whitesides GM (1991) Tetrahedron Lett 32: 4835

    Google Scholar 

  315. Bissett DL, Anderson RL (1973) Biochem Biophys Res Commun 52: 641

    Google Scholar 

  316. Bissett DL, Anderson RL (1974) J Bacteriol 119: 698

    Google Scholar 

  317. Bissett DL, Anderson RL (1974) J Bacteriol 117: 318

    Google Scholar 

  318. Hamilton IR, Lebtag H (1979) J Bacteriol 140: 1102

    Google Scholar 

  319. Crow VL, Davey GP, Pearce LE, Thomas TD (1983) J Bacteriol 153: 76

    PubMed  Google Scholar 

  320. Kanatani K, Tahara T, Yoshida K, Miura H, Sakamoto M, Oshimura M (1992) Biosci Biotechnol Biochem 56: 826

    Google Scholar 

  321. Szumilo T (1981) FEBS Lett 124: 270

    Google Scholar 

  322. Markwell J, Shimamoto GT, Bissett DL, Anderson RL (1976) Biochem Biophys Res Commun 71: 221

    Google Scholar 

  323. Lengeler J (1977) MGG Mol Gen Genet 152: 83

    Google Scholar 

  324. Bissett DL, Anderson RL (1980) J Biol Chem 255: 8750

    Google Scholar 

  325. Anderson RL, Bissett DL (1982) Methods Enzymol 90: 228

    Google Scholar 

  326. Crow VL, Thomas TD (1982) J Bacteriol 151: 600

    Google Scholar 

  327. Anderson RL, Markwell JP (1982) Methods Enzymol 90: 232

    Google Scholar 

  328. Fessner W-D, Eyrisch O (1992) Angew Chem Int Ed Engl 31: 56

    Google Scholar 

  329. Limsowtin GKY, Crow VL, Pearce LE (1986) FEMS Microbiol Lett 33: 79

    Google Scholar 

  330. Yu PL, Limsowtin GKY, Crow VL, Pearce LE (1988) Appl Microbiol Biotechnol 28: 471

    Google Scholar 

  331. Van Rooijen RJ, Van Schalkwijk S, De Vos WM (1991) J Biol Chem 266: 7176

    Google Scholar 

  332. Rosey EL, Oskouian B, Stewart GC (1991) J Bacteriol 173: 5992

    Google Scholar 

  333. Jagusztyn-Krynicka EK, Hansen JB, Crow VL, Thomas TD, Honeyman AL, Curtiss R (1992) J Bacteriol 174: 6152

    Google Scholar 

  334. Rosey EL, Stewart GC (1992) J Bacteriol 174: 6159

    Google Scholar 

  335. Alpert CA, unpublished

    Google Scholar 

  336. Takagi Y (1966) Methods Enzymol 9: 542

    Google Scholar 

  337. Chiu TH, Evans KL, Feingold DS (1975) Methods Enzymol 42: 264

    Google Scholar 

  338. Chiu T-H, Feingold DS (1969) Biochemistry 8: 98

    Google Scholar 

  339. Sawada H, Takagi Y (1964) Biochim Biophys Acta 92: 26

    Google Scholar 

  340. Schwartz NB, Feingold DS (1972) Bioinorg Chem 1: 233

    Google Scholar 

  341. Schwartz NB, Feingold DS (1972) Bioinorg Chem 2: 75

    Google Scholar 

  342. Badía J, Gimenez R, Baldomà L, Barnes E, Fessner W-D, Aguilar J (1991) J Bacteriol 173: 5144

    Google Scholar 

  343. Moralejo P, Egan SM, Hidalgo E, Aguilar J (1993) J Bacteriol 175: 5585

    Google Scholar 

  344. Nishitani J, Wilcox G (1991) Gene 105: 37

    Google Scholar 

  345. Axmann S, Schulz GE, unpublished

    Google Scholar 

  346. Fessner W-D, Schneider A, Eyrisch O, Sinerius G, Badia J (1993) Tetrahedron Asymmetry 4: 1183

    Google Scholar 

  347. Fessner W-D, Badia J, Eyrisch O, Schneider A, Sinerius G (1992) Tetrahedron Lett 33: 5231

    Google Scholar 

  348. Eyrisch O (1994) Ph.D. thesis, University of Freiburg

    Google Scholar 

  349. Mazur AW (1991) Galactose Oxidase: Selected Properties and Synthetic Applications. In: Bednarski MD, Simon ES (eds) Enzymes in Carbohydrate Synthesis. American Chemical Society, Washington, vol. 466, p 99

    Google Scholar 

  350. Eyrisch O, Keller M, Fessner W-D (1994) Tetrahedron Lett 35: 9013

    Google Scholar 

  351. Ghalambor MA, Heath EC (1962) J Biol Chem 237: 2427

    Google Scholar 

  352. Ghalambor MA, Heath EC (1966) Methods Enzymol 9: 538

    Google Scholar 

  353. Chen YM, Zhu Y, Lin ECC (1987) MGG Mol Gen Genet 210: 331

    Google Scholar 

  354. Lu Z, Lin ECC (1989) Nucleic Acids Res 17: 4883

    Google Scholar 

  355. Ozaki A, Toone EJ, von der Osten CH, Sinskey AJ, Whitesides GM (1990) J Am Chem Soc 112: 4970

    Google Scholar 

  356. Dreyer M, Schulz GE, unpublished

    Google Scholar 

  357. Fessner W-D, Schneider A, Held H, Sinerius G, Walter C, Hixon M, Schloss JV (1996) Angew Chem Int Ed Engl 35: 0000

    Google Scholar 

  358. Mildvan AS, Kobes RD, Rutter WJ (1971) Biochemistry 10: 1191

    Google Scholar 

  359. Smith GM, Mildvan AS, Harper ET (1980) Biochemistry 19: 1248

    Google Scholar 

  360. Smith GM, Mildvan AS (1981) Biochemistry 20: 4340

    Google Scholar 

  361. Belasco JG, Knowles JR (1983) Biochemistry 22: 122

    Google Scholar 

  362. Schneider A (1994) Ph.D. thesis, University of Freiburg

    Google Scholar 

  363. Racker E (1952) J Biol Chem 196: 347

    Google Scholar 

  364. Hoffee P, Rosen OM, Horecker BL (1966) Methods Enzymol 9: 545

    Google Scholar 

  365. Hoffee PA (1968) Arch Biochem Biophys 126: 795

    Google Scholar 

  366. Hoffee P, Rosen OM, Horecker BL (1965) J Biol Chem 240: 1512

    Google Scholar 

  367. Stura EA, Ghosh S, Garcia-Junceda E, Chen LR, Wong C-H, Wilson IA (1995) Proteins 22: 67

    Google Scholar 

  368. Valentin-Hansen P, Boetius F, Hammer-Jespersen K, Svendsen I (1982) Eur J Biochem 125: 561

    Google Scholar 

  369. Gijsen HJM, Wong C-H (1995) J Am Chem Soc 117: 2947

    Google Scholar 

  370. Chen L, Dumas DP, Wong C-H (1992) J Am Chem Soc 114: 741

    Google Scholar 

  371. Barbas CF, Wang YF, Wong C-H (1990) J Am Chem Soc 112: 2013

    Google Scholar 

  372. Gijsen HJM, Wong C-H (1994) J Am Chem Soc 116: 8422

    Google Scholar 

  373. Wong C-H, Garcia-Junceda E, Chen LR, Blanco O, Gijsen HJM, Steensma DH (1995) J Am Chem Soc 117: 3333

    Google Scholar 

  374. Beisswenger R, Kula MR (1991) Appl Microbiol Biotechnol 34: 604

    Google Scholar 

  375. Levering PR, Croes LM, Dijkhuizen L (1986) Arch Microbiol 144: 279

    Google Scholar 

  376. Yanase H, Matsuzaki K, Sato Y, Kita K, Sato Y, Kato N (1992) Appl Microbiol Biotechnol 37: 301

    Google Scholar 

  377. Yanase H, Koike Y, Matsuzaki K, Kita K, Sato Y, Kato N (1992) Biosci Biotechnol Biochem 56: 541

    Google Scholar 

  378. Kemp MB (1974) Biochem J 139: 129

    Google Scholar 

  379. Brockamp HP, Steigel A, Kula MR (1993) Liebigs Ann Chem 621

    Google Scholar 

  380. Beisswenger R, Snatzke G, Thiem J, Kula MR (1991) Tetrahedron Lett 32: 3159

    Google Scholar 

  381. Lill U, Pirzer P, Kukla D, Huber R, Eggerer H (1980) Hoppe Seyler's Z Physiol Chem 361: 875

    Google Scholar 

  382. Banki K, Halladay D, Perl A (1994) J Biol Chem 269: 2847

    Google Scholar 

  383. Schaaf I, Hohmann S, Zimmermann FK (1990) Eur J Biochem 188: 597

    Google Scholar 

  384. Williams JF, Blackmore PF (1983) Int J Biochem 15: 797

    Google Scholar 

  385. Arora KK, Collins JG, MacLeod JK, Williams JF (1988) Biol Chem Hoppe Seyler 369: 549

    Google Scholar 

  386. Horecker BL, Smyrniotis PZ (1953) J Am Chem Soc 75: 2021

    Google Scholar 

  387. Moradian A, Benner SA (1992) J Am Chem Soc 114: 6980

    Google Scholar 

  388. Grazi E, Mangiarotti M, Pontremoli S (1962) Biochemistry 1: 628

    Google Scholar 

  389. Horecker BL, Smyrniotis PZ (1953) J Am Chem Soc 75: 1009

    Google Scholar 

  390. Datta A, Racker E (1961) J Biol Chem 236: 624

    Google Scholar 

  391. Racker E, de la Haba G, Leder IG (1953) J Am Chem Soc 75: 1010

    Google Scholar 

  392. Racker E (1961) Transketolase. In: Boyer P, Lardy H, Myrbäck K (eds) The Enzymes. Academic Press, New York, vol. 5, p 397.

    Google Scholar 

  393. Villafranca JJ, Axelrod B (1971) J Biol Chem 246: 3126

    Google Scholar 

  394. de la Haba G, Leder IG, Racker E (1955) J Biol Chem 214: 409

    Google Scholar 

  395. Sprenger GA, Schörken U, Sprenger G, Sahm H (1995) Eur J Biochem 230: 525

    Google Scholar 

  396. French C, Ward JM (1995) Biotechnol Lett 17: 247

    Google Scholar 

  397. Kotchetov GA (1982) Methods Enzymol 90: 209

    Google Scholar 

  398. Iida A, Teshiba S, Mizobuchi K (1993) J Bacteriol 175: 5375

    Google Scholar 

  399. Sprenger GA (1993) Biochim Biophys Acta 1216: 307

    Google Scholar 

  400. Chen J-H, Gibson JL, McCue LA, Tabita FR (1991) J Biol Chem 266: 20447

    Google Scholar 

  401. Fletcher TS, Kwee IL, Nakada T, Largman C, Martin BM (1992) Biochemistry 31: 1892

    Google Scholar 

  402. Sundstrom M, Lindqvist Y, Schneider G, Hellman U, Ronne H (1993) J Biol Chem 268: 24346

    Google Scholar 

  403. Metzger MH, Hollenberg CP (1994) Appl Microbiol Biotechnol 42: 319

    Google Scholar 

  404. McCool BA, Plonk SG, Martin PR, Singleton CK (1993) J Biol Chem 268: 1397

    Google Scholar 

  405. Lindqvist Y, Schneider G, Ermler U, Sundström M (1992) EMBO J 11: 2373

    Google Scholar 

  406. Nikkola M, Lindqvist Y, Schneider G (1994) J Mol Biol 238: 387

    Google Scholar 

  407. König S, Schellenberger A, Neef H, Schneider G (1994) J Biol Chem 269: 10879

    Google Scholar 

  408. Nilsson U, Lindqvist Y, Kluger R, Schneider G (1993) FEBS Lett 326: 145

    Google Scholar 

  409. Bolte J, Demuynck C, Samaki H (1987) Tetrahedron Lett 28: 5525

    Google Scholar 

  410. Dickens F, Williamson DH (1958) Biochem J 68: 74

    Google Scholar 

  411. Dickens F (1962) Biochem Prep 9: 86

    Google Scholar 

  412. Zimmermann F, Fessner W-D, unpublished

    Google Scholar 

  413. Dalmas V, Demuynck C (1993) Tetrahedron Asymmetry 4: 2383

    Google Scholar 

  414. Wood T (1973) Prep Biochem 3: 509

    Google Scholar 

  415. Mocali A, Aldinucci D, Paoletti F (1985) Carbohydr Res 143: 288

    Google Scholar 

  416. Effenberger F, Null V, Ziegler T (1992) Tetrahedron Lett 33: 5157

    Google Scholar 

  417. Kobori Y, Myles DC, Whitesides GM (1992) J Org Chem 57: 5899

    Google Scholar 

  418. Demuynck C, Bolte J, Hecquet L, Dalmas V (1991) Tetrahedron Lett 32: 5085

    Google Scholar 

  419. Ziegler T, Straub A, Effenberger F (1988) Angew Chem Int Ed Engl 27: 716

    Google Scholar 

  420. Effenberger F, Straub A, Null V (1992) Liebigs Ann Chem 1297

    Google Scholar 

  421. Hecquet L, Bolte J, Demuynck C (1994) Tetrahedron 50: 8677

    Google Scholar 

  422. Dalmas V, Demuynck C (1993) Tetrahedron Asymmetry 4: 1169

    Google Scholar 

  423. Csuk R, Glänzer BI (1991) Chem Rev 91: 49

    Google Scholar 

  424. Servi S (1990) Synthesis 1

    Google Scholar 

  425. Crout DHG, Dalton H, Hutchinson DW, Miyagoshi M (1991) J Chem Soc Perkin Trans I 1329

    Google Scholar 

  426. Bringer-Meyer S, Schmiz K-L, Sahm S (1986) Arch Microbiol 146: 105

    Google Scholar 

  427. Kuo DJ, Dikdan G, Jordan F (1986) J Biol Chem 261: 3316

    Google Scholar 

  428. Farrenkopf B, Jordan F (1992) Protein Express Purif 3: 101

    Google Scholar 

  429. Zehender H, Trescher D, Ullrich J (1987) Eur J Biochem 167: 149

    Google Scholar 

  430. Mücke U, König S, Hübner G (1995) Biol Chem Hoppe Seyler 376: 111

    Google Scholar 

  431. Neale AD, Scopes RK, Wettenhall REH, Hoogenraad NJ (1987) J Bacteriol 169: 1024

    Google Scholar 

  432. Kellermann E, Seeboth PG, Hollenberg CP (1986) Nucleic Acids Res 14: 8963

    Google Scholar 

  433. Hohmann S (1991) J Bacteriol 173: 7963

    Google Scholar 

  434. Hohmann S, Cederberg H (1990) Eur J Biochem 188: 615

    Google Scholar 

  435. Bräu B, Sahm H (1986) Arch Microbiol 144: 296

    Google Scholar 

  436. Conway T, Osman YA, Konnan JI, Hoffmann EM, Ingram LO (1987) J Bacteriol 169: 949

    Google Scholar 

  437. Neale AD, Scopes RK, Wettenhall REH, Hoogenraad NJ (1987) Nucleic Acids Res 15: 1753

    Google Scholar 

  438. Lowe SE, Zeikus JG (1992) J Gen Microbiol 138: 803

    Google Scholar 

  439. Alvarez ME, Rosa AL, Temporini ED, Wolstenholme A, Panzetta G, Patrito L, Maccioni HJF (1993) Gene 130: 253

    Google Scholar 

  440. Kelley PM, Godfrey K, Lal SK, Alleman M (1991) Plant Mol Biol 17: 1259

    Google Scholar 

  441. Dyda F, Furey W, Swaminathan S, Sax M, Farrenkopf B, Jordan F (1993) Biochemistry 32: 6165

    Google Scholar 

  442. Muller YA, Lindqvist Y, Furey W, Schulz GE, Jordan F, Schneider G (1993) Structure 1: 95

    Google Scholar 

  443. Abraham W-R, Stumpf B (1987) Z Naturforsch 42 C: 559

    Google Scholar 

  444. Chen GC, Jordan F (1984) Biochemistry 23: 3576

    Google Scholar 

  445. Bornemann S, Crout DHG, Dalton H, Hutchinson DW, Dean G, Thomson N, Turner MM (1993) J Chem Soc Perkin Trans I 309

    Google Scholar 

  446. Crout DHG, Littlechild J, Morrey SM (1986) J Chem Soc Perkin Trans I 105

    Google Scholar 

  447. Kren V, Crout DHG, Dalton H, Hutchinson DW, Konig W, Turner MM, Dean G, Thomson N (1993) J Chem Soc Chem Commun 341

    Google Scholar 

  448. Grue-Søresen G, Spencer ID (1988) J Am Chem Soc 110: 3714

    Google Scholar 

  449. Fuganti C, Grasselli P (1977) Chem Ind 983

    Google Scholar 

  450. Fuganti C, Grasselli P, Poli G, Servi S, Zorzella A (1988) J Chem Soc Chem Commun 1619

    Google Scholar 

  451. Karasek MA, Greenberg DM (1957) J Biol Chem 227: 191

    Google Scholar 

  452. Malkin LI, Greenberg DM (1964) Biochim Biophys Acta 85: 117

    Google Scholar 

  453. Greenberg DM (1967) Methods Enzymol 931

    Google Scholar 

  454. Bruns FH, Fiedler L (1958) Biochem Z 330: 324

    Google Scholar 

  455. Bruns FH, Fiedler L (1958) Nature 181: 1533

    Google Scholar 

  456. Naoi M, Takahashi T, Kuno N, Nagatsu T (1987) Biochem Biophys Res Commun 143: 482

    Google Scholar 

  457. Dainty RH (1970) Biochem J 117: 585

    Google Scholar 

  458. Vassilev VP, Uchiyama T, Kajimoto T, Wong C-H (1995) Tetrahedron Lett 36: 4081

    Google Scholar 

  459. Herbert RB, Wilkinson B, Ellames GJ (1994) Can J Chem 72: 114

    Google Scholar 

  460. Herbert RB, Wilkinson B, Ellames GJ, Kunec EK (1993) J Chem Soc Chem Commun 205

    Google Scholar 

  461. Ura D, Hashimukai T, Matsumoto T, Fukuhara N (1991) CA 115: 90657q

    Google Scholar 

  462. Anderson DM, Hsiao H-H (1992) Enzymatic method for L-serine production. In: Rozzell D, Wagner F (eds) Biocatalytic Production of Amino Acids & Derivatives. Hanser, Munich, p 23

    Google Scholar 

  463. Ulevitch RJ, Kallen RG (1977) Biochemistry 16: 5342

    Google Scholar 

  464. Schirch L, Peterson D (1980) J Biol Chem 255: 7801

    Google Scholar 

  465. Sakamoto M, Masuda T, Yanagimoto Y, Nakano Y, Kitaoka S (1991) Agric Biol Chem 55: 2243

    Google Scholar 

  466. Miyazaki SS, Toki S, Izumi Y, Yamada H (1987) Eur J Biochem 162: 533

    Google Scholar 

  467. Miyazaki SS, Toki S, Izumi Y, Yamada H (1987) Agric Biol Chem 51: 2587

    Google Scholar 

  468. Ide H, Hamaguchi K, Kobata S, Murakami A, Kimura Y, Makino K, Kamada M, Miyamoto S, Nagaya T, Kamogawa K, Izumi Y (1992) J Chromatogr 596: 203

    Google Scholar 

  469. Turner SR, Ireland R, Morgan C, Rawsthorne S (1992) J Biol Chem 267: 13528

    Google Scholar 

  470. Garrow TA, Brenner AA, Whitehead VM, Chen X-N, Duncan RG, Korenberg JR, Shane B (1993) J Biol Chem 268: 11910

    Google Scholar 

  471. Byrne PC, Sanders PG, Snell K (1992) Biochem J 286: 117

    Google Scholar 

  472. Jagath-Reddy J, Ganesan K, Saithri HS, Datta A, Rao NA (1995) Eur J Biochem 230: 533

    Google Scholar 

  473. Martini F, Angelaccio S, Pascarella S, Barra D, Bossa F, Schirch V (1987) J Biol Chem 262: 5499

    Google Scholar 

  474. Martini F, Maras B, Tanci P, Angelaccio S, Pascarella S, Barra D, Bossa F, Schirch V (1989) J Biol Chem 264: 8509

    Google Scholar 

  475. McNeil JB, McIntosh EM, Taylor BV, Zhang FR, Tang S, Bognar AL (1994) J Biol Chem 269: 9155

    Google Scholar 

  476. Chistoserdova LV, Lidstrom ME (1994) J Bacteriol 176: 6759

    Google Scholar 

  477. Urbanowski ML, Plamann MD, Stauffer LT, Stauffer GV (1984) Gene 27: 47

    Google Scholar 

  478. Chan VL, Bingham HL (1990) Gene 101: 51

    Google Scholar 

  479. McClung CR, Davis CR, Page KM, Denome SA (1992) Mol Cell Biol 12: 1412

    Google Scholar 

  480. Miyata A, Yoshida T, Yamaguchi K, Yokoyama C, Tanabe T, Toh H, Mitsunaga T, Izumi Y (1993) Eur J Biochem 212: 745

    Google Scholar 

  481. Plamann MD, Stauffer LT, Urbanowski ML, Stauffer GV (1983) Nucleic Acids Res 11: 2065

    Google Scholar 

  482. Rossbach S, Hennecke H (1991) Mol Microbiol 5: 39

    Google Scholar 

  483. Lotz BT, Gasparski CM, Peterson K, Miller MJ (1990) J Chem Soc Chem Commun 16: 1107

    Google Scholar 

  484. Saeed A, Young DW (1992) Tetrahedron 48: 2507

    Google Scholar 

  485. Chen MS, Schirch L (1973) J Biol Chem 248: 7979

    Google Scholar 

  486. Billhardt UM, Stein P, Whitesides GM (1989) Bioorg Chem 17: 1

    Google Scholar 

  487. Patel SS, Conlon HD, Walt DR (1986) J Org Chem 51: 2842

    Google Scholar 

  488. Ouyang T, Walt DR, Patel SS (1990) Bioorg Chem 18: 131

    Google Scholar 

  489. Patel SS, Walt DR (1987) J Biol Chem 262: 7132

    Google Scholar 

  490. Kumari S, Tishel R, Eisenbach M, Wolfe AJ (1995) J Bacteriol 177: 2878

    Google Scholar 

  491. Martin DP, Bibart RT, Drueckhammer DG (1994) J Am Chem Soc 116: 4660

    Google Scholar 

  492. Kao CM, Katz L, Khosla C (1994) Science 265: 509

    Google Scholar 

  493. Kao CM, Luo GL, Katz L, Cane DE, Khosla C (1994) J Am Chem Soc 116: 11612

    Google Scholar 

  494. McDaniel R, Ebert-Khosla S, Hopwood DA, Khosla C (1993) Science 262: 1546

    Google Scholar 

  495. McDaniel R, Ebert-Khosla S, Hopwood DA, Khosla C (1994) J Am Chem Soc 116: 10855

    Google Scholar 

  496. McDaniel R, Ebert-Khosla S, Hopwood DA, Khosla C (1995) Nature 375: 549

    Google Scholar 

  497. Tsoi CJ, Khosla C (1995) Chem Biol 2: 355

    Google Scholar 

  498. Shen B, Hutchinson CR (1993) Science 262: 1535

    Google Scholar 

  499. Rohr J (1995) Angew Chem Int Ed Engl 34: 881

    Google Scholar 

  500. Decker H, Haag S, Udvarnoki G, Rohr J (1995) Angew Chem Int Ed Engl 34: 1107

    Google Scholar 

  501. Effenberger F (1994) Angew Chem Int Ed Engl 33: 1555

    Google Scholar 

  502. Jorns MS (1979) J Biol Chem 254: 12145

    Google Scholar 

  503. Hochuli F (1983) Helv Chim Acta 66: 489

    Google Scholar 

  504. Becker W, Pfeil E (1966) Biochem Z 346: 301

    Google Scholar 

  505. Smitskamp-Wilms E, Brussee J, van der Gen A (1991) Recl Trav Chim Pays-Bas 110: 209

    Google Scholar 

  506. Lauble H, Muller K, Schindelin H, Forster S, Effenberger F (1994) Proteins 19: 343

    Google Scholar 

  507. Cheng IP, Poulton JE (1993) Plant Cell Physiol 34: 1139

    Google Scholar 

  508. Woker R, Champluvier B, Kula MR (1992) J Chromatogr 584: 85

    Google Scholar 

  509. Klempier N, Griengl H, Hayn M (1993) Tetrahedron Lett 34: 4769

    Google Scholar 

  510. van Scharrenburg GJM, Sloothaak JB, Kruse CG, Smitskamp-Wilms E, Brussee J (1993) Ind J Chem B 32: 16

    Google Scholar 

  511. Wajant H, Mundry KW (1993) Plant Sci 89: 127

    Google Scholar 

  512. Wajant H, Mundry KW, Pfizenmaier K (1994) Plant Mol Biol 26: 735

    Google Scholar 

  513. Xu L-L, Singh BK, Conn EE (1988) Arch Biochem Biophys 263: 256

    Google Scholar 

  514. Albrecht J, Jansen I, Kula MR (1993) Biotechnol Appl Biochem 17: 191

    Google Scholar 

  515. Hughes J, Decarvalho JPC, Hughes MA (1994) Arch Biochem Biophys 311: 496

    Google Scholar 

  516. Brussee J, Roos EC, van der Gen A (1988) Tetrahedron Lett 29: 4485

    Google Scholar 

  517. Becker W, Pfeil E (1966) J Am Chem Soc 88: 4299

    Google Scholar 

  518. Becker W, Freund H, Pfeil E (1965) Angew Chem Int Ed Engl 4: 1079

    Google Scholar 

  519. Niedermeyer U, Kula M-R (1990) Angew Chem Int Ed Engl 29: 386

    Google Scholar 

  520. Effenberger F, Ziegler T, Förster S (1987) Angew Chem Int Ed Engl 26: 458

    Google Scholar 

  521. Ognyanov VI, Datcheva VK, Kyler KS (1991) J Am Chem Soc 113: 6992

    Google Scholar 

  522. Brussee J, Loos WT, Kruse CG, van der Gen A (1990) Tetrahedron 46: 979

    Google Scholar 

  523. Huuhtanen TT, Kanerva LT (1992) Tetrahedron Asymmetry 3: 1223

    Google Scholar 

  524. Zandbergen P, van der Linden J, Brussee J, van der Gen A (1991) Synth Commun 21: 1387

    Google Scholar 

  525. Kiljunen E, Kanerva LT (1994) Tetrahedron Asymmetry 5: 311

    Google Scholar 

  526. Effenberger F, Hörsch B, Förster S, Ziegler T (1990) Tetrahedron Lett 31: 1249

    Google Scholar 

  527. Klempier N, Pichler U, Griengl H (1995) Tetrahedron Asymmetry 6: 845

    Google Scholar 

  528. Ziegler T, Hörsch B, Effenberger F (1990) Synthesis 575–578

    Google Scholar 

  529. Menendez E, Brieva R, Rebolledo F, Gotor V (1995) J Chem Soc Chem Commun 989–990

    Google Scholar 

  530. Effenberger F, Hörsch B, Weingart F, Ziegler T, Kühner S (1991) Tetrahedron Lett 32:2605

    Google Scholar 

  531. Effenberger F, Eichhorn J, Roos J (1995) Tetrahedron Asymmetry 6: 271

    Google Scholar 

  532. Henderson I, Sharpless KB, Wong C-H (1994) J Am Chem Soc 116: 558

    Google Scholar 

  533. Badia J, Baldomà L, Aguilar J, Boronat A (1989) FEMS Microbiol Lett 65: 253

    Google Scholar 

  534. Card PJ, Hitz WD, Ripp KG (1986) J Am Chem Soc 108: 158

    Google Scholar 

  535. Berger A, de Raadt A, Gradnig G, Grasser M, Loew H, Stuetz AE (1992) Tetrahedron Lett 33: 7125

    Google Scholar 

  536. Look GC, Fotsch CH, Wong C-H (1993) Acc Chem Res 26: 182

    Google Scholar 

  537. Wong C-H, Halcomb RL, Ichikawa Y, Kajimoto T (1995) Angew Chem Int Ed Engl 34: 412

    Google Scholar 

  538. Pederson RL, Kim MJ, Wong C-H (1988) Tetrahedron Lett 29: 4645

    Google Scholar 

  539. Liu KKC, Kajimoto T, Chen L, Zhong Z, Ichikawa Y, Wong C-H (1991) J Org Chem 56: 6280

    Google Scholar 

  540. Zhou PZ, Salleh HM, Chan PCM, Lajoie G, Honek JF, Nambiar PTC, Ward OP (1993) Carbohydr Res 239: 155

    Google Scholar 

  541. Lees WJ, Whitesides GM (1992) Bioorg Chem 20: 173

    Google Scholar 

  542. Hung RR, Straub JA, Whitesides GM (1991) J Org Chem 56: 3849

    Google Scholar 

  543. Winchester B, Fleet GWJ (1992) Glycobiology 2: 199

    Google Scholar 

  544. Henderson I, Laslo K, Wong C-H (1994) Tetrahedron Lett 35: 359

    Google Scholar 

  545. Holt KE, Leeper FJ, Handa S (1994) J Chem Soc Perkin Trans I 231–234

    Google Scholar 

  546. Chou WC, Chen LH, Fang JM, Wong C-H (1994) J Am Chem Soc 116: 6191

    Google Scholar 

  547. Kuan KT, Weber DS, Sottile L, Goux WJ (1992) Carbohydr Res 225: 123

    Google Scholar 

  548. Fleischmann RD, et al. (1995) Science 269: 496

    Google Scholar 

  549. Marshall E (1994) Science 266: 208

    Google Scholar 

  550. Sakowicz R, Gold M, Jones JB (1995) J Am Chem Soc 117: 2387

    Google Scholar 

  551. Wilks HM, Moreton KM, Halsall DJ, Hart KW, Sessions RD, Clarke AR, Holbrook JJ (1992) Biochemistry 31: 7802

    Google Scholar 

  552. Wang QP, Graham RW, Trimbur D, Warren RAJ, Withers SG (1994) J Am Chem Soc 116: 11594

    Google Scholar 

  553. Oshima T (1994) Curr Opin Struct Biol 4: 623

    Google Scholar 

  554. Bocanegra JA, Scrutton NS, Perham RN (1993) Biochemistry 32: 2737

    Google Scholar 

  555. Mittl PRE, Berry A, Scrutton NS, Perham RN, Schulz GE (1994) Protein Sci 3: 1504

    Google Scholar 

  556. Reymond JL, Chen YW (1995) Tetrahedron Lett 36: 2575

    Google Scholar 

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  1. Institut für Organische Chemie der Rheinisch-Westfälischen Technischen Hochschule Aachen, Professor-Pirlet-Str. 1, D-52056, Aachen, Germany

    Wolf-Dieter Fessner & Christiane Walter

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  1. Wolf-Dieter Fessner
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F. P. Schmidtchen

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Fessner, WD., Walter, C. (1996). Enzymatic C-C bond formation in asymmetric synthesis. In: Schmidtchen, F.P. (eds) Bioorganic Chemistry. Topics in Current Chemistry, vol 184. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3-540-61388-9_63

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