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.
This is a preview of subscription content, log in via an institution.
Preview
Unable to display preview. Download preview PDF.
9 References
Testa B, Trager WF (1990) Chirality 2: 129
Wainer IW, Drayer DE (1988) Drug Stereochemistry. Marcel Dekker, New York
Ariens EJ, van Rensen JJS, Welling W (1988) Stereoselectivity of Pesticides. Elsevier, Amsterdam
Whitesides GM, Wong C-H (1985) Angew Chem Int Ed Engl 24: 617
Jones JB (1986) Tetrahedron 42: 3351
Davies HG, Green RH, Kelly DR, Roberts SM (1989) Biotransformations in Preparative Organic Chemistry. Academic Press, London
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
Gerhartz W (1991) Enzymes in Industry: Production and Applications. VCH, Weinheim
Boland W, Froessl C, Lorenz M (1991) Synthesis 12: 1049
Schellenberger V, Jakubke HD (1991) Angew Chem Int Ed Engl 30: 1437
Holland HL (1992) Organic Synthesis with Oxidative Enzymes. VCH, Weinheim
David S, Augé C, Gautheron C (1991) Adv Carbohydr Chem Biochem 49: 175
Blanch HW, Clark DS (1991) Applied Biocatalysis, vol 1. Marcel Dekker, New York
Drauz K, Waldmann H (1995) Enzyme Catalysis in Organic Synthesis. A Comprehensive Handbook. VCH, Weinheim
Rozzell D, Wagner F (1992) Biocatalytic Production of Amino Acids & Derivatives. Hanser, Munich
Wong C-H, Whitesides GM (1994) Enzymes in Synthetic Organic Chemistry. Pergamon, Oxford
Faber K (1995) Biotransformations in Organic Chemistry, 2nd edn. Springer, Berlin
Servi S (1992) Microbial Reagents in Organic Synthesis, vol 381. Kluwer Academic, Dordrecht
Halgas J (1992) Biocatalysts in Organic Synthesis. Elsevier, Amsterdam
Poppe L, Novák L (1992) Selective Biocatalysis. A Synthetic Approach. VCH, Weinheim
Toone EJ, Simon ES, Bednarski MD, Whitesides GM (1989) Tetrahedron 45: 5365
Azerad R (1995) Bull Soc Chim Fr 132: 17
Santaniello E, Ferraboschi P, Grisenti P, Manzocchi A (1992) Chem Rev 92: 1071
Waldmann H, Sebastian D (1994) Chem Rev 94: 911
David S, Auge C, Gautheron C (1992) Adv Carbohydr Chem Biochem 49: 175
Varki A (1994) Proc Natl Acad Sci USA 91: 7390
Carlos TM, Harlan JM (1994) Blood 84: 2068
Hynes RO, Lander AD (1992) Cell 68: 303
Wegner CD (1994) Adhesion Molecules. Academic Press, London
Chibata I (1978) Immobilized Enzymes. Research and Development. Wiley, New York
Trevan MD (1980) Immobilized Enzymes. An Introduction and Applications in Biotechnology. Wiley, New York
Mosbach K (1976) Methods Enzymol 44, (1987) 135, (1987) 136, (1988) 137
Woodley JM (1992) Immobilized Biocatalysts. In: Smith K (ed) Solids Supports and Catalysts in Organic Synthesis. Ellis Horwood, Chichester, p 254
Chenault HK, Whitesides GM (1987) Appl Biochem Biotechnol 14: 147
Chenault HK, Simon ES, Whitesides GM (1988) Biotechnol Genet Eng Rev 6: 221
Schreiber SL, Verdine GL (1991) Tetrahedron 47: 2543
Hedstrom L (1994) Curr Opin Struct Biol 4: 608
Janda KD (1994) Proc Natl Acad Sci USA 91: 10779
Gordon EM, Barrett RW, Dower WJ, Fodor SPA, Gallop MA (1994) J Med Chem 37: 1385
Gallop MA, Barrett RW, Dower WJ, Fodor SPA, Gordon EM (1994) J Med Chem 37: 1233
Kluger R (1990) Chem Rev 90: 1151
Schomburg D, Salzmann M (1990–1995) Enzyme Handbook. Springer, Berlin
Horecker BL, Tsolas O, Lai CY (1972) Aldolases. In: Boyer PD (ed) The Enzymes. 3 edn. Academic Press, New York, vol. VII, p 213
Trombetta G, Balboni G, di Iasio A, Grazi E (1977) Biochem Biophys Res Commun 74: 1297
Kuo DJ, Rose IA (1985) Biochemistry 24: 3947
Grazi E, Cheng T, Horecker BL (1962) Biochem Biophys Res Commun 7: 250
Kadonaga JT, Knowles JR (1983) Biochemistry 22: 130
Webb EC (1992) Enzyme Nomenclature. Academic Press, San Diego
Demerec M, Adelberg EA, Clark AJ, Hartman PE (1966) Genetics 54: 61
Smith HO, Nathans D (1973) J Mol Biol 81: 419
Kluger R (1990) Chem Rev 90: 1151
Littlechild JA, Watson HC (1993) Trends Biochem Sci 18: 36
Morris AJ, Tolan DR (1993) J Biol Chem 268: 1095
Morris AJ, Tolan DR (1994) Biochemistry 33: 12291
Pollak A, Blumenfeld H, Wax M, Baughn RL, Whitesides GM (1980) J Am Chem Soc 102: 6324
Bossow B, Berke W, Wandrey C (1992) BioEngineering 8: 12
Sobolov SB, Bartoszkomalik A, Oeschger TR, Montelbano MM (1994) Tetrahedron Lett 35: 7751
Goße C, Fessner W-D, unpublished
Kragl U, Gödde A, Wandrey C, Lubin N, Augé C (1994) J Chem Soc Perkin Trans I 119
Kragl U, Gygax D, Ghisalba O, Wandrey C (1991) Angew Chem Int Ed Engl 30: 827
Kragl U, Niedermeyer U, Kula M-R, Wandrey C (1990) Ann N Y Acad Sci 613: 617
Raetz CRH, Dowhan W (1990) J Biol Chem 265: 1235
Unger FM (1981) Adv Carbohydr Chem Biochem 38: 323
Varki A (1993) Glycobiology 3: 97
Schauer R, Wember M, Wirtz-Peitz F, Ferreira do Amaral C (1971) Hoppe Seyler's Z Physiol Chem 352: 1073
Comb DG, Roseman S (1960) J Biol Chem 235: 2529
Deijl CM, Vliegenthart JFG (1983) Biochem Biophys Res Commun 111: 668
Baumann W, Freidenreich J, Weisshaar G, Brossmer R, Friebolin H (1989) Biol Chem Hoppe Seyler 370: 141
Uchida Y, Tsukada Y, Sugimori T (1984) J Biochem 96: 507
Ohta Y, Shimosaka M, Murata K, Tsukada Y, Kimura A (1986) Appl Microbiol Biotechnol 24: 386
Aisaka K, Tamura S, Arai Y, Uwajima T (1987) Biotechnol Lett 9: 633
Ohta Y, Tsukada Y, Sugimori T, Murata K, Kimura A (1989) Agric Biol Chem 53: 477
Aisaka K, Igarashi A, Yamaguchi K, Uwajima T (1991) Biochem J 276: 541
Izard T, Lawrence MC, Malby RL, Lilley GG, Colman PM (1994) Structure 2: 361
Schauer R, Stoll S, Zbiral E, Schreiner E, Brandstetter HH, Vasella A, Baumberger F (1987) Glycoconjugate J 4: 361
Kraulis PJ (1991) J Appl Crystallogr 24: 946
Kim MJ, Hennen WJ, Sweers HM, Wong C-H (1988) J Am Chem Soc 110: 6481
Harlan JM, Liu DY (1992) Adhesion — Its Role in Inflammatory Disease. W.H. Freeman and Co, New York
Kelm S, Schauer R, Manuguerra JC, Gross HJ, Crocker PR (1994) Glycoconjugate J 11: 576
Troy FA (1992) Glycobiology 2: 5
Wiley DC, Skehel JJ (1987) Annu Rev Biochem 56: 365
Augé C, David S, Gautheron C, Malleron A, Cavayé B (1988) New J Chem 12: 733
Simon ES, Bednarski MD, Whitesides GM (1988) J Am Chem Soc 110: 7159
Lin CH, Sugai T, Halcomb RL, Ichikawa Y, Wong C-H (1992) J Am Chem Soc 114: 10138
Ichikawa Y, Liu JLC, Shen GJ, Wong C-H (1991) J Am Chem Soc 113: 6300
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
Liu JLC, Shen GJ, Ichikawa Y, Rutan JF, Zapata G, Vann WF, Wong C-H (1992) J Am Chem Soc 114: 3901
Augé C, Gautheron C, David S, Malleron A, Cavayé B, Bouxom B (1990) Tetrahedron 46: 201
Koppert K, Brossmer R (1992) Tetrahedron Lett 33: 8031
Sparks MA, Williams KW, Lukacs C, Schrell A, Priebe G, Spaltenstein A, Whitesides GM (1993) Tetrahedron 49: 1
Zhou PZ, Salleh HM, Honek JF (1993) J Org Chem 58: 264
Fitz W, Wong C-H (1994) J Org Chem 59: 8279
Gross HJ, Brossmer R (1988) Eur J Biochem 177: 583
Brossmer R, Gross HJ (1994) Methods Enzymol 247: 177
Brossmer R, Gross HJ (1994) Methods Enzymol 247: 153
Jacob GS, Kirmaier C, Abbas SZ, Howard SC, Steininger CN, Welply JK, Scudder P (1995) Biochemistry 34: 1210
Varki A (1992) Glycobiology 2: 25
Halcomb RL, Fitz W, Wong C-H (1994) Tetrahedron Asymmetry 5: 2437
Kong DCM, von Itzstein M (1995) Tetrahedron Lett 36: 957
Isecke R, Brossmer R (1994) Tetrahedron 50: 7445
Schrell A, Whitesides GM (1990) Liebigs Ann Chem 1111
Kragl U, Gödde A, Wandrey C, Kinzy W, Cappon JJ, Lugtenburg J (1993) Tetrahedron Asymmetry 4: 1193
Augé C, Bouxom B, Cavayé B, Gautheron C (1989) Tetrahedron Lett 30: 2217
David S, Malleron A, Cavayé B (1992) New J Chem 16: 751
Gautheron LNC, Ichikawa Y, Wong C-H (1991) J Am Chem Soc 113: 7816
Ladisch S, Hasegawa A, Li RX, Kiso M (1995) Biochemistry 34: 1197
Knappmann BR, Kula MR (1990) Appl Microbiol Biotechnol 33: 324
Ghalambor MA, Heath EC (1966) J Biol Chem 241: 3222
Sugai T, Shen GJ, Ichikawa Y, Wong C-H (1993) J Am Chem Soc 115: 413
Hammond SM, Claesson A, Jansson AM, Larsson L-G, Pring BG, Town CM, Ekström B (1987) Nature 327: 730
Claesson A (1987) J Org Chem 52: 4414
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
Scopes RK (1984) Anal Biochem 136: 525
Shelton MC, Toone EJ (1995) Tetrahedron Asymmetry 6: 207
Knappmann BR, Elnawawy MA, Schlegel HG, Kula MR (Erratum (1995) Carbohydr Res 272: C1)
Egan SE, Fliege R, Tong S, Shibata A, Wolf RE, Conway T (1992) J Bacteriol 174: 4638
Carter AT, Pearson BM, Dickinson JR, Lancashire WE (1993) Gene 130: 155
Conway T, Yi KC, Egan SE, Wolf REJ, Rowley DL (1991) J Bacteriol 173: 5247
Conway T, Fliege R, Jones-Kilpatrick D, Liu J, Barnell WO, Egan SE (1991) Mol Microbiol 5: 2901
Hugouvieux-Cotte-Pattat N, Robert-Baudouy J (1994) Mol Microbiol 11: 67
Suzuki N, Wood WA (1980) J Biol Chem 255: 3427
Hammerstedt RH, Möhler H, Decker KA, Ersfeld D, Wood WA (1975) Methods Enzymol 42: 258
Mavridis IM, Hatada MH, Tulinsky A, Lebioda L (1982) J Mol Biol 162: 419
Dekker EE, Kitson RP (1992) J Biol Chem 267: 10507
Dekker EE, Kobes RD, Grady SR (1975) Methods Enzymol 42: 280
Dekker EE, Nishihara H, Grady SR (1975) Methods Enzymol 42: 285
Kuratomi K, Fukunaga K (1963) Biochim Biophys Acta 78: 617
Maitra U, Dekker EE (1964) J Biol Chem 239: 1485
Rosso RG, Adams E (1967) J Biol Chem 242: 5524
Vlahos CJ, Dekker EE (1988) J Biol Chem 263: 11683
Patil RV, Dekker EE (1992) J Bacteriol 174: 102
Taha TSM, Deits TL (1994) Biochem Biophys Res Commun 200: 459
Meloche HP, Mehler L (1973) J Biol Chem 248: 6333
Meloche HP, Monti CT (1975) J Biol Chem 250: 6875
Scholtz JM, Schuster SM (1984) Bioorg Chem 12: 229
Floyd NC, Liebster MH, Turner NJ (1992) J Chem Soc Perkin Trans I 1085
Allen ST, Heintzelman GR, Toone EJ (1992) J Org Chem 57: 426
Nishihara H, Dekker EE (1972) J Biol Chem 247: 5079
Meloche HP, O'Connell EL (1982) Methods Enzymol 90: 263
Dahms AS, Anderson RL (1972) J Biol Chem 247: 2238
Anderson RL, Dahms AS (1975) Methods Enzymol 42: 269
Dahms AS (1974) Biochem Biophys Res Commun 60: 1433
Dahms AS, Donald A (1982) Methods Enzymol 90: 269
Augé C, Delest V (1993) Tetrahedron Asymmetry 4: 1165
Elshafei AM, Abdel-Fatah OM (1989) Enzyme Microb Technol 11: 367
Elshafei AM, Mohawed SM, Ammar MS, Abdel-Fatah OM (1995) Int J Gen Mol Microbiol 67: 211
Auge C, Delest V (1995) Tetrahedron Asymmetry 6: 863
Fish DC, Blumenthal HJ (1966) Methods Enzymol 9: 529
Hirschbein BL, Mazenod FP, Whitesides GM (1982) J Org Chem 47: 3765
Simon ES, Grabowski S, Whitesides GM (1989) J Am Chem Soc 111: 8920
Blacklow RS, Warren L (1962) J Biol Chem 237: 3520
Annunziato PW, Wright LF, Vann WF, Silver RP (1995) J Bacteriol 177: 312
Ganguli S, Zapata G, Wallis T, Reid C, Boulnois G, Vann WF, Roberts IS (1994) J Bacteriol 176: 4583
Edwards U, Müller A, Hammerschmidt S, Gerardy-Schahn R, Frosch M (1994) Mol Microbiol 14: 141
Brossmer R, Rose U, Kasper D, Smith TL, Grasmuk H, Unger FM (1980) Biochem Biophys Res Commun 96: 1282
Raetz CRH (1993) J Bacteriol 175: 5745
Doong RL, Ahmad S, Jensen RA (1991) Plant Cell Environ 14: 113
Levin DH, Racker E (1959) J Biol Chem 234: 2532
Woisetschläger M, Högenauer G (1987) MGG Mol Gen Genet 207: 369
Woisetschläger M, Högenauer G (1986) J Bacteriol 168: 437
Dotson GD, Dua RK, Clemens JC, Wooten EW, Woodard RW (1995) J Biol Chem 270: 13698
Ray PH (1980) J Bacteriol 141: 635
Ray PH (1982) Method Enzymol 83: 525
Baasov T, Sheffer-Dee-Noor S, Kohen A, Jakob A, Belakhov V (1993) Eur J Biochem 217: 991
Yanase H, Okuda M, Kita K, Shibata K, Sakai Y, Kato Y (1995) Appl Microbiol Biotechnol 43: 228
Bednarski MD, Crans DC, DiCosimo R, Simon ES, Stein PD, Whitesides GM, Schneider MJ (1988) Tetrahedron Lett 29: 427
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
Doong RL, Jensen RA (1992) New Phytol 121: 165
Srinivasan PR, Sprinson DB (1959) J Biol Chem 234: 716
Hurwitz J, Weissbach A (1959) J Biol Chem 234: 710
Zurawski G, Brown KD, Killingly D, Yanofsky C (1978) Proc Natl Acad Sci USA 75: 4271
Shultz J, Hermodson MA, Garner CC, Herrmann KM (1984) J Biol Chem 259: 9655
Ray JM, Yanofsky C, Baeuerle R (1988) J Bacteriol 170: 5500
Weaver LM, Herrmann KM (1990) J Bacteriol 172: 6581
Sprinson DB, Srinivasan PR, Katagiri M (1962) Methods Enzymol 5: 394
Schoner R, Herrmann KM (1976) J Biol Chem 251: 5440
Paravicini G, Schmidheini T, Braus G (1989) Eur J Biochem 186: 361
Ray JM, Bauerle R (1991) J Bacteriol 173: 1894
Stuart F, Hunter IS (1993) Biochim Biophys Acta 1161: 209
Muday GK, Herrmann KM (1990) J Bacteriol 172: 2259
Dyer WE, Weaver LM, Zhao J, Kuhn DN, Weller SC, Herrmann KM (1990) J Biol Chem 265: 1608
Weaver LM, Pinto JEBP, Herrmann KM (1993) Bioorg Med Chem Lett 3: 1421
Doong RL, Gander JE, Ganson RJ, Jensen RA (1992) Physiol Plant 84: 351
Reimer LM, Conley DL, Pompliano DL, Frost JW (1986) J Am Chem Soc 108: 8010
Montchamp J-L, Piehler LT, Frost JW (1992) J Am Chem Soc 114: 4453
Draths KM, Frost JW (1990) J Am Chem Soc 112: 1657
Draths KM, Ward TL, Frost JW (1992) J Am Chem Soc 114: 9725
Draths KM, Frost JW (1995) J Am Chem Soc 117: 2395
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
Fessner W-D (1993) GIT Fachz Lab 37: 951
Lebherz HG (1972) Biochemistry 11: 2243
Lebherz HG, Rutter WJ (1969) Biochemistry 8: 109
Harris CE, Kobes RD, Teller DC, Rutter WJ (1969) Biochemistry 8: 2442
Schwartz NB, Abram D, Feingold DS (1974) Biochemistry 13: 1726
Fessner W-D, Sinerius G, Schneider A, Dreyer M, Schulz GE, Badia J, Aguilar J (1991) Angew Chem Int Ed Engl 30: 555
Taylor JF, Green AA, Cori GT (1948) J Biol Chem 173: 591
Vanderheiden BS, Meinhart JO, Dodson RG, Krebs EG (1962) J Biol Chem 237: 2095
Richards OC, Rutter WJ (1961) J Biol Chem 236: 3177
Periana RA, Motiu-DeGrood R, Chiang Y, Hupe DJ (1980) J Am Chem Soc 102: 3923
Fessner W-D, Sinerius G (1994) Angew Chem Int Ed Engl 33: 209
Stribling D (1974) Biochem J 141: 725
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
Whitesides GM, personal communication
Paterson MC, Norton IL, Hartman FC (1972) Biochemistry 11: 2070
Magnien A, Le Clef B, Biellmann JF (1984) Biochemistry 23: 6858
Weis K, Fessner W-D, unpublished
Eyrisch O, Fessner W-D (1995) Angew Chem Int Ed Engl 34: 1639
Fessner W-D, Sinerius G (1994) Bioorg Med Chem 2: 639
von der Osten CH, Sinskey AJ, Barbas CF, Pederson RL, Wang YF, Wong C-H (1989) J Am Chem Soc 111: 3924
Götz F, Fischer S, Schleifer K-H (1980) Eur J Biochem 108: 295
Dreyer MK, Schulz GE (1993) J Mol Biol 231: 549
Sinerius G, Schneider A, Goße C, Fessner W-D, unpublished
Rutter WJ, Richards OC, Woodfin BM (1961) J Biol Chem 236: 3193
Spolter PD, Adelman RC, Weinhouse S (1965) J Biol Chem 240: 1327
Berthiaume L, Tolan DR, Sygusch J (1993) J Biol Chem 268: 10826
Berthiaume L, Loisel TP, Sygusch J (1991) J Biol Chem 266: 17099
Richard JP (1984) J Am Chem Soc 106: 4926
Richard JP (1993) Biochem Soc Trans 21: 549
Phillips SA, Thornalley PJ (1993) Eur J Biochem 212: 101
Sinerius G (1994) Ph.D. thesis, University of Freiburg
Waagen V, Barua TK, Anthonsen HW, Hansen LK, Fossli DJ, Hough E, Anthonsen T (1994) Tetrahedron 50: 10055
Effenberger F, Straub A (1987) Tetrahedron Lett 28: 1641
Pederson RL, Esker J, Wong C-H (1991) Tetrahedron 47: 2643
Colbran RL, Jones JKN, Matheson NK, Rozema I (1967) Carbohydr Res 4: 355
Jung SH, Jeong JH, Miller P, Wong C-H (1994) J Org Chem 59: 7182
Crans DC, Whitesides GM (1985) J Am Chem Soc 107: 7019
Crans DC, Kazlauskas RJ, Hirschbein BL, Wong C-H, Abril O, Whitesides GM (1987) Methods Enzymol 136: 263
Meyerhof O, Lohmann K, Schuster P (1936) Biochem Zeitschr 286: 301
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
Fessner W-D, Walter C (1992) Angew Chem Int Ed Engl 31: 614
Colombo G, Tate PW, Girotti AW, Kemp RG (1975) J Biol Chem 250: 9404
Babul J (1978) J Biol Chem 253: 4350
Eyrisch O, Sinerius G, Fessner W-D (1993) Carbohydr Res 238: 287
Walter C (1996) Ph.D. thesis, RWTH Aachen
Liu KKC, Pederson RL, Wong C-H (1991) J Chem Soc, Perkin Trans 1: 2669
Kajimoto T, Liu KKC, Pederson RL, Zhong Z, Ichikawa Y, Porco JAJ, Wong C-H (1991) J Am Chem Soc 113: 6187
Kajimoto T, Chen L, Liu KKC, Wong C-H (1991) J Am Chem Soc 113: 6678
Esders TW, Michrina CA (1979) J Biol Chem 254: 2710
Arth H-L, Sinerius G, Fessner W-D (1995) Liebigs Ann Chem 2037
Drueckhammer DG, Durrwachter JR, Pederson RL, Crans DC, Daniels L, Wong C-H (1989) J Org Chem 54: 70
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
Nour-Eldeen AF, Craig MM, Gresser MJ (1985) J Biol Chem 260: 6836
Crans DC, Schelble SM, Theisen LA (1991) J Org Chem 56: 1266
London J (1974) J Biol Chem 249: 7977
Sugimoto S, Nosoh Y (1971) Biochim Biophys Acta 235: 210
Freeze H, Brock TD (1970) J Bacteriol 101: 541
Ingram JM, Hochster RM (1967) Can J Biochem 45: 929
Stribling D, Perham RN (1973) Biochem J 131: 833
Barnes EM, Akagi JM, Himes RH (1971) Biochim Biophys Acta 227: 199
Krishnan G, Altekar W (1991) Eur J Biochem 195: 343
Baldwin SA, Perham RN (1978) Biochem J 169: 643
Brockamp HP, Kula MR (1990) Appl Microbiol Biotechnol 34: 287
Lebherz HG, Rutter WJ (1973) J Biol Chem 248: 1650
Bai NJ, Pai MR, Murthy PS, Venkitasubramanian TA (1975) Arch Biochem Biophys 168: 235
Schnarrenberger C, Pelzer-Reith B, Yatsuki H, Freund S, Jacobshagen S, Hori K (1994) Arch Biochem Biophys 313: 173
Russell GK, Gibbs M (1967) Biochim Biophys Acta 132: 145
Willard J, Gibbs M (1968) Biochim Biophys Acta 151: 438
Fluri R, Ramasarma T, Horecker BL (1967) Eur J Biochem 1: 117
Krüger I, Schnarrenberger C (1983) Eur J Biochem 136: 101
Lebherz HG, Leadbetter MM, Bradshaw RA (1984) J Biol Chem 259: 1011
Heil JA, Lebherz HG (1978) J Biol Chem 253: 6599
Valentin ML, Bolte J (1993) Tetrahedron Lett 34: 8103
Fernández-Sousa J, Gavilanes FG, Gavilanes JG, Paredes JA (1978) Arch Biochem Biophys 188: 456
Brenner-Holzach O (1979) Arch Biochem Biophys 194: 321
Kochman M, Kwiatkowska D (1972) Arch Biochem Biophys 152: 856
Certa U, Ghersa P, Döbeli H, Matile H, Kocher HP, Shrivastava IK, Shaw AR, Perrin LH (1988) Science 240: 1036
Ting S-M, Sia CL, Lai CY, Horecker BL (1971) Arch Biochem Biophys 144: 485
Komatsu SK, Feeney R (1970) Biochim Biophys Acta 206: 305
Yeltman DR, Harris BG (1977) Biochim Biophys Acta 484: 188
Rajkumar TV, Woodfin BM, Rutter WJ (1966) Methods Enzym 9: 491
Marquardt RR (1971) Can J Biochem 49: 658
Peanasky RJ, Lardy HA (1990) J Biol Chem 265: 1608
Gracy RW, Lacko AG, Horecker BL (1969) J Biol Chem 244: 3913
Penhoet EE, Kochman M, Rutter WJ (1969) Biochemisty 8: 4391
Izzo P, Costanzo P, Lupo A, Rippa E, Paolella G, Salvatore F (1988) Eur J Biochem 174: 569
von der Osten CH, Barbas CF, Wong C-H, Sinskey AJ (1989) Mol Microbiol 3: 1625
Schwelberger HG, Kohlwein SD, Paltauf F (1989) Eur J Biochem 180: 301
Mutoh N, Hayashi Y (1994) Biochim Biophys Acta 1183: 550
Berthiaume L, Beaudry D, Lazure C, Tolan DR, Sygusch J (1989) Arch Biochem Biophys 272: 281
Alefounder PR, Baldwin SA, Perham RN, Short NJ (1989) Biochem J 257: 529
Sygusch J, Beaudry D, Allaire M (1987) Proc Natl Acad Sci USA 84: 7846
Gamblin SJ, Davies GJ, Grimes JM, Jackson RM, Littlechild JA, Watson HC (1991) J Mol Biol 219: 573
Gamblin SJ, Cooper B, Millar JR, Davies GJ, Littlechild JA, Watson HC (1990) FEBS Lett 262: 282
Hester G, Brenner-Holzach O, Rossi FA, Struck-Donatz M, Winterhalter KH, Smit JDG, Piontek K (1991) FEBS Lett 292: 237
Brockamp HP, Kula MR (1990) Tetrahedron Lett 31: 7123
Walter C, Petersen M, Fessner W-D, unpublished
Wong C-H, Whitesides GM (1983) J Org Chem 48: 3199
Schmid W, Whitesides GM (1990) J Am Chem Soc 112: 9670
Schmid W, Heidlas J, Mathias JP, Whitesides GM (1992) Liebigs Ann Chem 95
Borysenko CW, Spaltenstein A, Straub JA, Whitesides GM (1980) J Am Chem Soc 111: 9275
Wong C-H, Mazenod FP, Whitesides GM (1983) J Org Chem 48: 3493
Durrwachter JR, Sweers HM, Nozaki K, Wong C-H (1986) Tetrahedron Lett 27: 1261
Peters J, Brockamp HP, Minuth T, Grothus M, Steigel A, Kula MR, Elling L (1993) Tetrahedron Asymmetry 4: 1173
Durrwachter JR, Wong C-H (1988) J Org Chem 53: 4175
Schneider A (1990) Diploma thesis, University of Freiburg
Jaeschke G, Goße C, Petersen M, Fessner W-D, unpublished
Bednarski MD, Waldmann HJ, Whitesides GM (1986) Tetrahedron Lett 27: 5807
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
Lees WJ, Whitesides GM (1993) J Org Chem 58: 1887
Straub A, Effenberger F, Fischer P (1990) J Org Chem 55: 3926
Fessner W-D, unpublished
Angyal SJ (1969) Angew Chem Int Ed Engl 8: 157
Jones JKN, Sephton HH (1960) Can J Chem 38: 753
Kapuscinski M, Franke FP, Flanigan I, MacLeod JK, Williams JF (1985) Carbohydr Res 140: 69
Paoletti F, Williams JF, Horecker BL (1979) Arch Biochem Biophys 198: 614
Durrwachter JR, Drueckhammer DG, Nozaki K, Sweers HM, Wong C-H (1986) J Am Chem Soc 108: 7812
Turner NJ, Whitesides GM (1989) J Am Chem Soc 111: 624
Liu KKC, Wong C-H (1992) J Org Chem 57: 4789
Maliakel BP, Schmid W (1993) J Carbohydr Chem 12: 415
Nicotra F, Panza L, Russo G, Verani A (1993) Tetrahedron Asymmetry 4: 1203
Matsumoto K, Shimagaki M, Nakata T, Oishi T (1993) Tetrahedron Lett 34: 4935
Shimagaki M, Muneshima H, Kubota M, Oishi T (1993) Chem Pharm Bull 41: 282
Schultz M, Waldmann H, Kunz H, Vogt W (1990) Liebigs Ann Chem 1019
Myles DC, Andrulis PJI, Whitesides GM (1991) Tetrahedron Lett 32: 4835
Bissett DL, Anderson RL (1973) Biochem Biophys Res Commun 52: 641
Bissett DL, Anderson RL (1974) J Bacteriol 119: 698
Bissett DL, Anderson RL (1974) J Bacteriol 117: 318
Hamilton IR, Lebtag H (1979) J Bacteriol 140: 1102
Crow VL, Davey GP, Pearce LE, Thomas TD (1983) J Bacteriol 153: 76
Kanatani K, Tahara T, Yoshida K, Miura H, Sakamoto M, Oshimura M (1992) Biosci Biotechnol Biochem 56: 826
Szumilo T (1981) FEBS Lett 124: 270
Markwell J, Shimamoto GT, Bissett DL, Anderson RL (1976) Biochem Biophys Res Commun 71: 221
Lengeler J (1977) MGG Mol Gen Genet 152: 83
Bissett DL, Anderson RL (1980) J Biol Chem 255: 8750
Anderson RL, Bissett DL (1982) Methods Enzymol 90: 228
Crow VL, Thomas TD (1982) J Bacteriol 151: 600
Anderson RL, Markwell JP (1982) Methods Enzymol 90: 232
Fessner W-D, Eyrisch O (1992) Angew Chem Int Ed Engl 31: 56
Limsowtin GKY, Crow VL, Pearce LE (1986) FEMS Microbiol Lett 33: 79
Yu PL, Limsowtin GKY, Crow VL, Pearce LE (1988) Appl Microbiol Biotechnol 28: 471
Van Rooijen RJ, Van Schalkwijk S, De Vos WM (1991) J Biol Chem 266: 7176
Rosey EL, Oskouian B, Stewart GC (1991) J Bacteriol 173: 5992
Jagusztyn-Krynicka EK, Hansen JB, Crow VL, Thomas TD, Honeyman AL, Curtiss R (1992) J Bacteriol 174: 6152
Rosey EL, Stewart GC (1992) J Bacteriol 174: 6159
Alpert CA, unpublished
Takagi Y (1966) Methods Enzymol 9: 542
Chiu TH, Evans KL, Feingold DS (1975) Methods Enzymol 42: 264
Chiu T-H, Feingold DS (1969) Biochemistry 8: 98
Sawada H, Takagi Y (1964) Biochim Biophys Acta 92: 26
Schwartz NB, Feingold DS (1972) Bioinorg Chem 1: 233
Schwartz NB, Feingold DS (1972) Bioinorg Chem 2: 75
Badía J, Gimenez R, Baldomà L, Barnes E, Fessner W-D, Aguilar J (1991) J Bacteriol 173: 5144
Moralejo P, Egan SM, Hidalgo E, Aguilar J (1993) J Bacteriol 175: 5585
Nishitani J, Wilcox G (1991) Gene 105: 37
Axmann S, Schulz GE, unpublished
Fessner W-D, Schneider A, Eyrisch O, Sinerius G, Badia J (1993) Tetrahedron Asymmetry 4: 1183
Fessner W-D, Badia J, Eyrisch O, Schneider A, Sinerius G (1992) Tetrahedron Lett 33: 5231
Eyrisch O (1994) Ph.D. thesis, University of Freiburg
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
Eyrisch O, Keller M, Fessner W-D (1994) Tetrahedron Lett 35: 9013
Ghalambor MA, Heath EC (1962) J Biol Chem 237: 2427
Ghalambor MA, Heath EC (1966) Methods Enzymol 9: 538
Chen YM, Zhu Y, Lin ECC (1987) MGG Mol Gen Genet 210: 331
Lu Z, Lin ECC (1989) Nucleic Acids Res 17: 4883
Ozaki A, Toone EJ, von der Osten CH, Sinskey AJ, Whitesides GM (1990) J Am Chem Soc 112: 4970
Dreyer M, Schulz GE, unpublished
Fessner W-D, Schneider A, Held H, Sinerius G, Walter C, Hixon M, Schloss JV (1996) Angew Chem Int Ed Engl 35: 0000
Mildvan AS, Kobes RD, Rutter WJ (1971) Biochemistry 10: 1191
Smith GM, Mildvan AS, Harper ET (1980) Biochemistry 19: 1248
Smith GM, Mildvan AS (1981) Biochemistry 20: 4340
Belasco JG, Knowles JR (1983) Biochemistry 22: 122
Schneider A (1994) Ph.D. thesis, University of Freiburg
Racker E (1952) J Biol Chem 196: 347
Hoffee P, Rosen OM, Horecker BL (1966) Methods Enzymol 9: 545
Hoffee PA (1968) Arch Biochem Biophys 126: 795
Hoffee P, Rosen OM, Horecker BL (1965) J Biol Chem 240: 1512
Stura EA, Ghosh S, Garcia-Junceda E, Chen LR, Wong C-H, Wilson IA (1995) Proteins 22: 67
Valentin-Hansen P, Boetius F, Hammer-Jespersen K, Svendsen I (1982) Eur J Biochem 125: 561
Gijsen HJM, Wong C-H (1995) J Am Chem Soc 117: 2947
Chen L, Dumas DP, Wong C-H (1992) J Am Chem Soc 114: 741
Barbas CF, Wang YF, Wong C-H (1990) J Am Chem Soc 112: 2013
Gijsen HJM, Wong C-H (1994) J Am Chem Soc 116: 8422
Wong C-H, Garcia-Junceda E, Chen LR, Blanco O, Gijsen HJM, Steensma DH (1995) J Am Chem Soc 117: 3333
Beisswenger R, Kula MR (1991) Appl Microbiol Biotechnol 34: 604
Levering PR, Croes LM, Dijkhuizen L (1986) Arch Microbiol 144: 279
Yanase H, Matsuzaki K, Sato Y, Kita K, Sato Y, Kato N (1992) Appl Microbiol Biotechnol 37: 301
Yanase H, Koike Y, Matsuzaki K, Kita K, Sato Y, Kato N (1992) Biosci Biotechnol Biochem 56: 541
Kemp MB (1974) Biochem J 139: 129
Brockamp HP, Steigel A, Kula MR (1993) Liebigs Ann Chem 621
Beisswenger R, Snatzke G, Thiem J, Kula MR (1991) Tetrahedron Lett 32: 3159
Lill U, Pirzer P, Kukla D, Huber R, Eggerer H (1980) Hoppe Seyler's Z Physiol Chem 361: 875
Banki K, Halladay D, Perl A (1994) J Biol Chem 269: 2847
Schaaf I, Hohmann S, Zimmermann FK (1990) Eur J Biochem 188: 597
Williams JF, Blackmore PF (1983) Int J Biochem 15: 797
Arora KK, Collins JG, MacLeod JK, Williams JF (1988) Biol Chem Hoppe Seyler 369: 549
Horecker BL, Smyrniotis PZ (1953) J Am Chem Soc 75: 2021
Moradian A, Benner SA (1992) J Am Chem Soc 114: 6980
Grazi E, Mangiarotti M, Pontremoli S (1962) Biochemistry 1: 628
Horecker BL, Smyrniotis PZ (1953) J Am Chem Soc 75: 1009
Datta A, Racker E (1961) J Biol Chem 236: 624
Racker E, de la Haba G, Leder IG (1953) J Am Chem Soc 75: 1010
Racker E (1961) Transketolase. In: Boyer P, Lardy H, Myrbäck K (eds) The Enzymes. Academic Press, New York, vol. 5, p 397.
Villafranca JJ, Axelrod B (1971) J Biol Chem 246: 3126
de la Haba G, Leder IG, Racker E (1955) J Biol Chem 214: 409
Sprenger GA, Schörken U, Sprenger G, Sahm H (1995) Eur J Biochem 230: 525
French C, Ward JM (1995) Biotechnol Lett 17: 247
Kotchetov GA (1982) Methods Enzymol 90: 209
Iida A, Teshiba S, Mizobuchi K (1993) J Bacteriol 175: 5375
Sprenger GA (1993) Biochim Biophys Acta 1216: 307
Chen J-H, Gibson JL, McCue LA, Tabita FR (1991) J Biol Chem 266: 20447
Fletcher TS, Kwee IL, Nakada T, Largman C, Martin BM (1992) Biochemistry 31: 1892
Sundstrom M, Lindqvist Y, Schneider G, Hellman U, Ronne H (1993) J Biol Chem 268: 24346
Metzger MH, Hollenberg CP (1994) Appl Microbiol Biotechnol 42: 319
McCool BA, Plonk SG, Martin PR, Singleton CK (1993) J Biol Chem 268: 1397
Lindqvist Y, Schneider G, Ermler U, Sundström M (1992) EMBO J 11: 2373
Nikkola M, Lindqvist Y, Schneider G (1994) J Mol Biol 238: 387
König S, Schellenberger A, Neef H, Schneider G (1994) J Biol Chem 269: 10879
Nilsson U, Lindqvist Y, Kluger R, Schneider G (1993) FEBS Lett 326: 145
Bolte J, Demuynck C, Samaki H (1987) Tetrahedron Lett 28: 5525
Dickens F, Williamson DH (1958) Biochem J 68: 74
Dickens F (1962) Biochem Prep 9: 86
Zimmermann F, Fessner W-D, unpublished
Dalmas V, Demuynck C (1993) Tetrahedron Asymmetry 4: 2383
Wood T (1973) Prep Biochem 3: 509
Mocali A, Aldinucci D, Paoletti F (1985) Carbohydr Res 143: 288
Effenberger F, Null V, Ziegler T (1992) Tetrahedron Lett 33: 5157
Kobori Y, Myles DC, Whitesides GM (1992) J Org Chem 57: 5899
Demuynck C, Bolte J, Hecquet L, Dalmas V (1991) Tetrahedron Lett 32: 5085
Ziegler T, Straub A, Effenberger F (1988) Angew Chem Int Ed Engl 27: 716
Effenberger F, Straub A, Null V (1992) Liebigs Ann Chem 1297
Hecquet L, Bolte J, Demuynck C (1994) Tetrahedron 50: 8677
Dalmas V, Demuynck C (1993) Tetrahedron Asymmetry 4: 1169
Csuk R, Glänzer BI (1991) Chem Rev 91: 49
Servi S (1990) Synthesis 1
Crout DHG, Dalton H, Hutchinson DW, Miyagoshi M (1991) J Chem Soc Perkin Trans I 1329
Bringer-Meyer S, Schmiz K-L, Sahm S (1986) Arch Microbiol 146: 105
Kuo DJ, Dikdan G, Jordan F (1986) J Biol Chem 261: 3316
Farrenkopf B, Jordan F (1992) Protein Express Purif 3: 101
Zehender H, Trescher D, Ullrich J (1987) Eur J Biochem 167: 149
Mücke U, König S, Hübner G (1995) Biol Chem Hoppe Seyler 376: 111
Neale AD, Scopes RK, Wettenhall REH, Hoogenraad NJ (1987) J Bacteriol 169: 1024
Kellermann E, Seeboth PG, Hollenberg CP (1986) Nucleic Acids Res 14: 8963
Hohmann S (1991) J Bacteriol 173: 7963
Hohmann S, Cederberg H (1990) Eur J Biochem 188: 615
Bräu B, Sahm H (1986) Arch Microbiol 144: 296
Conway T, Osman YA, Konnan JI, Hoffmann EM, Ingram LO (1987) J Bacteriol 169: 949
Neale AD, Scopes RK, Wettenhall REH, Hoogenraad NJ (1987) Nucleic Acids Res 15: 1753
Lowe SE, Zeikus JG (1992) J Gen Microbiol 138: 803
Alvarez ME, Rosa AL, Temporini ED, Wolstenholme A, Panzetta G, Patrito L, Maccioni HJF (1993) Gene 130: 253
Kelley PM, Godfrey K, Lal SK, Alleman M (1991) Plant Mol Biol 17: 1259
Dyda F, Furey W, Swaminathan S, Sax M, Farrenkopf B, Jordan F (1993) Biochemistry 32: 6165
Muller YA, Lindqvist Y, Furey W, Schulz GE, Jordan F, Schneider G (1993) Structure 1: 95
Abraham W-R, Stumpf B (1987) Z Naturforsch 42 C: 559
Chen GC, Jordan F (1984) Biochemistry 23: 3576
Bornemann S, Crout DHG, Dalton H, Hutchinson DW, Dean G, Thomson N, Turner MM (1993) J Chem Soc Perkin Trans I 309
Crout DHG, Littlechild J, Morrey SM (1986) J Chem Soc Perkin Trans I 105
Kren V, Crout DHG, Dalton H, Hutchinson DW, Konig W, Turner MM, Dean G, Thomson N (1993) J Chem Soc Chem Commun 341
Grue-Søresen G, Spencer ID (1988) J Am Chem Soc 110: 3714
Fuganti C, Grasselli P (1977) Chem Ind 983
Fuganti C, Grasselli P, Poli G, Servi S, Zorzella A (1988) J Chem Soc Chem Commun 1619
Karasek MA, Greenberg DM (1957) J Biol Chem 227: 191
Malkin LI, Greenberg DM (1964) Biochim Biophys Acta 85: 117
Greenberg DM (1967) Methods Enzymol 931
Bruns FH, Fiedler L (1958) Biochem Z 330: 324
Bruns FH, Fiedler L (1958) Nature 181: 1533
Naoi M, Takahashi T, Kuno N, Nagatsu T (1987) Biochem Biophys Res Commun 143: 482
Dainty RH (1970) Biochem J 117: 585
Vassilev VP, Uchiyama T, Kajimoto T, Wong C-H (1995) Tetrahedron Lett 36: 4081
Herbert RB, Wilkinson B, Ellames GJ (1994) Can J Chem 72: 114
Herbert RB, Wilkinson B, Ellames GJ, Kunec EK (1993) J Chem Soc Chem Commun 205
Ura D, Hashimukai T, Matsumoto T, Fukuhara N (1991) CA 115: 90657q
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
Ulevitch RJ, Kallen RG (1977) Biochemistry 16: 5342
Schirch L, Peterson D (1980) J Biol Chem 255: 7801
Sakamoto M, Masuda T, Yanagimoto Y, Nakano Y, Kitaoka S (1991) Agric Biol Chem 55: 2243
Miyazaki SS, Toki S, Izumi Y, Yamada H (1987) Eur J Biochem 162: 533
Miyazaki SS, Toki S, Izumi Y, Yamada H (1987) Agric Biol Chem 51: 2587
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
Turner SR, Ireland R, Morgan C, Rawsthorne S (1992) J Biol Chem 267: 13528
Garrow TA, Brenner AA, Whitehead VM, Chen X-N, Duncan RG, Korenberg JR, Shane B (1993) J Biol Chem 268: 11910
Byrne PC, Sanders PG, Snell K (1992) Biochem J 286: 117
Jagath-Reddy J, Ganesan K, Saithri HS, Datta A, Rao NA (1995) Eur J Biochem 230: 533
Martini F, Angelaccio S, Pascarella S, Barra D, Bossa F, Schirch V (1987) J Biol Chem 262: 5499
Martini F, Maras B, Tanci P, Angelaccio S, Pascarella S, Barra D, Bossa F, Schirch V (1989) J Biol Chem 264: 8509
McNeil JB, McIntosh EM, Taylor BV, Zhang FR, Tang S, Bognar AL (1994) J Biol Chem 269: 9155
Chistoserdova LV, Lidstrom ME (1994) J Bacteriol 176: 6759
Urbanowski ML, Plamann MD, Stauffer LT, Stauffer GV (1984) Gene 27: 47
Chan VL, Bingham HL (1990) Gene 101: 51
McClung CR, Davis CR, Page KM, Denome SA (1992) Mol Cell Biol 12: 1412
Miyata A, Yoshida T, Yamaguchi K, Yokoyama C, Tanabe T, Toh H, Mitsunaga T, Izumi Y (1993) Eur J Biochem 212: 745
Plamann MD, Stauffer LT, Urbanowski ML, Stauffer GV (1983) Nucleic Acids Res 11: 2065
Rossbach S, Hennecke H (1991) Mol Microbiol 5: 39
Lotz BT, Gasparski CM, Peterson K, Miller MJ (1990) J Chem Soc Chem Commun 16: 1107
Saeed A, Young DW (1992) Tetrahedron 48: 2507
Chen MS, Schirch L (1973) J Biol Chem 248: 7979
Billhardt UM, Stein P, Whitesides GM (1989) Bioorg Chem 17: 1
Patel SS, Conlon HD, Walt DR (1986) J Org Chem 51: 2842
Ouyang T, Walt DR, Patel SS (1990) Bioorg Chem 18: 131
Patel SS, Walt DR (1987) J Biol Chem 262: 7132
Kumari S, Tishel R, Eisenbach M, Wolfe AJ (1995) J Bacteriol 177: 2878
Martin DP, Bibart RT, Drueckhammer DG (1994) J Am Chem Soc 116: 4660
Kao CM, Katz L, Khosla C (1994) Science 265: 509
Kao CM, Luo GL, Katz L, Cane DE, Khosla C (1994) J Am Chem Soc 116: 11612
McDaniel R, Ebert-Khosla S, Hopwood DA, Khosla C (1993) Science 262: 1546
McDaniel R, Ebert-Khosla S, Hopwood DA, Khosla C (1994) J Am Chem Soc 116: 10855
McDaniel R, Ebert-Khosla S, Hopwood DA, Khosla C (1995) Nature 375: 549
Tsoi CJ, Khosla C (1995) Chem Biol 2: 355
Shen B, Hutchinson CR (1993) Science 262: 1535
Rohr J (1995) Angew Chem Int Ed Engl 34: 881
Decker H, Haag S, Udvarnoki G, Rohr J (1995) Angew Chem Int Ed Engl 34: 1107
Effenberger F (1994) Angew Chem Int Ed Engl 33: 1555
Jorns MS (1979) J Biol Chem 254: 12145
Hochuli F (1983) Helv Chim Acta 66: 489
Becker W, Pfeil E (1966) Biochem Z 346: 301
Smitskamp-Wilms E, Brussee J, van der Gen A (1991) Recl Trav Chim Pays-Bas 110: 209
Lauble H, Muller K, Schindelin H, Forster S, Effenberger F (1994) Proteins 19: 343
Cheng IP, Poulton JE (1993) Plant Cell Physiol 34: 1139
Woker R, Champluvier B, Kula MR (1992) J Chromatogr 584: 85
Klempier N, Griengl H, Hayn M (1993) Tetrahedron Lett 34: 4769
van Scharrenburg GJM, Sloothaak JB, Kruse CG, Smitskamp-Wilms E, Brussee J (1993) Ind J Chem B 32: 16
Wajant H, Mundry KW (1993) Plant Sci 89: 127
Wajant H, Mundry KW, Pfizenmaier K (1994) Plant Mol Biol 26: 735
Xu L-L, Singh BK, Conn EE (1988) Arch Biochem Biophys 263: 256
Albrecht J, Jansen I, Kula MR (1993) Biotechnol Appl Biochem 17: 191
Hughes J, Decarvalho JPC, Hughes MA (1994) Arch Biochem Biophys 311: 496
Brussee J, Roos EC, van der Gen A (1988) Tetrahedron Lett 29: 4485
Becker W, Pfeil E (1966) J Am Chem Soc 88: 4299
Becker W, Freund H, Pfeil E (1965) Angew Chem Int Ed Engl 4: 1079
Niedermeyer U, Kula M-R (1990) Angew Chem Int Ed Engl 29: 386
Effenberger F, Ziegler T, Förster S (1987) Angew Chem Int Ed Engl 26: 458
Ognyanov VI, Datcheva VK, Kyler KS (1991) J Am Chem Soc 113: 6992
Brussee J, Loos WT, Kruse CG, van der Gen A (1990) Tetrahedron 46: 979
Huuhtanen TT, Kanerva LT (1992) Tetrahedron Asymmetry 3: 1223
Zandbergen P, van der Linden J, Brussee J, van der Gen A (1991) Synth Commun 21: 1387
Kiljunen E, Kanerva LT (1994) Tetrahedron Asymmetry 5: 311
Effenberger F, Hörsch B, Förster S, Ziegler T (1990) Tetrahedron Lett 31: 1249
Klempier N, Pichler U, Griengl H (1995) Tetrahedron Asymmetry 6: 845
Ziegler T, Hörsch B, Effenberger F (1990) Synthesis 575–578
Menendez E, Brieva R, Rebolledo F, Gotor V (1995) J Chem Soc Chem Commun 989–990
Effenberger F, Hörsch B, Weingart F, Ziegler T, Kühner S (1991) Tetrahedron Lett 32:2605
Effenberger F, Eichhorn J, Roos J (1995) Tetrahedron Asymmetry 6: 271
Henderson I, Sharpless KB, Wong C-H (1994) J Am Chem Soc 116: 558
Badia J, Baldomà L, Aguilar J, Boronat A (1989) FEMS Microbiol Lett 65: 253
Card PJ, Hitz WD, Ripp KG (1986) J Am Chem Soc 108: 158
Berger A, de Raadt A, Gradnig G, Grasser M, Loew H, Stuetz AE (1992) Tetrahedron Lett 33: 7125
Look GC, Fotsch CH, Wong C-H (1993) Acc Chem Res 26: 182
Wong C-H, Halcomb RL, Ichikawa Y, Kajimoto T (1995) Angew Chem Int Ed Engl 34: 412
Pederson RL, Kim MJ, Wong C-H (1988) Tetrahedron Lett 29: 4645
Liu KKC, Kajimoto T, Chen L, Zhong Z, Ichikawa Y, Wong C-H (1991) J Org Chem 56: 6280
Zhou PZ, Salleh HM, Chan PCM, Lajoie G, Honek JF, Nambiar PTC, Ward OP (1993) Carbohydr Res 239: 155
Lees WJ, Whitesides GM (1992) Bioorg Chem 20: 173
Hung RR, Straub JA, Whitesides GM (1991) J Org Chem 56: 3849
Winchester B, Fleet GWJ (1992) Glycobiology 2: 199
Henderson I, Laslo K, Wong C-H (1994) Tetrahedron Lett 35: 359
Holt KE, Leeper FJ, Handa S (1994) J Chem Soc Perkin Trans I 231–234
Chou WC, Chen LH, Fang JM, Wong C-H (1994) J Am Chem Soc 116: 6191
Kuan KT, Weber DS, Sottile L, Goux WJ (1992) Carbohydr Res 225: 123
Fleischmann RD, et al. (1995) Science 269: 496
Marshall E (1994) Science 266: 208
Sakowicz R, Gold M, Jones JB (1995) J Am Chem Soc 117: 2387
Wilks HM, Moreton KM, Halsall DJ, Hart KW, Sessions RD, Clarke AR, Holbrook JJ (1992) Biochemistry 31: 7802
Wang QP, Graham RW, Trimbur D, Warren RAJ, Withers SG (1994) J Am Chem Soc 116: 11594
Oshima T (1994) Curr Opin Struct Biol 4: 623
Bocanegra JA, Scrutton NS, Perham RN (1993) Biochemistry 32: 2737
Mittl PRE, Berry A, Scrutton NS, Perham RN, Schulz GE (1994) Protein Sci 3: 1504
Reymond JL, Chen YW (1995) Tetrahedron Lett 36: 2575
Author information
Authors and Affiliations
Editor information
Rights and permissions
Copyright information
© 1996 Springer-Verlag
About this chapter
Cite this chapter
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
Download citation
DOI: https://doi.org/10.1007/3-540-61388-9_63
Published:
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-540-61388-6
Online ISBN: 978-3-540-68510-4
eBook Packages: Springer Book Archive