Advertisement

Synthetic applications of enzymatic reactions in organic solvents

  • A. L. Gutman
  • M. Shapira
Chapter
Part of the Advances in Biochemical Engineering/Biotechnology book series (ABE, volume 52)

Abstract

One of the most important properties of enzymes is their ability to catalyze reactions in a stereoselective manner. This has been used for many years by organic chemist, who have exploited enzymes as catalysts in asymmetric synthesis and resolution for the preparation of optically pure compounds. It is now well established that hydrolytic enzymes can function also in organic solvents and can be used for certain types of transformations which are diffucult or impossible to do in water. The present review surveys recent publications of preparatively useful transformations catalyzed by hydrolytic enzymes in nonaqueous media, which enable one to obtain a wide range of homochiral molecules. These transformations exploit the enzymes' enantioselectivity as well as prochiral selectivity. While in the former case the enzymatic reactions amount to a kinetic resolution with the yield of the desired enantiomer not higher than 50%, in the latter case it is often possible to convert a symmetrical prochiral molecule into a homochiral molecule in much higher chemical yields. In addition to the preparative aspects of nonaqueous enzymology, this review also surveys the recent literature related to some fundamental questions of this phenomenon, such as the effect of the nature of the organic solvent and of its water content on reaction rate and stereospecificity of the enzymatic reaction.

Keywords

Vinyl Acetate Kinetic Resolution Acyl Donor Allylic Alcohol Synthetic Application 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

List of symbols and abbreviations

Bn

benzyl

CAL

Candida antarctica lipase

CCL

Candida cylindracea lipase

CVL

Chromobacterium viscosum lipase

Da

Dalton

E

enantiomeric ratio

ee

enantiomeric excess

LAPH

liver acetone powder horse

MML

Mucor miehei lipase

PCL

Pseudomonas cepacia lipase

PEG

poly(ethylene glycol)

PFL

Pseudomonas fluorecens lipase

Ph

Phenyl

PPL

procine panacrease lipase

PSL

Pseudomonas species lipase

TBDPS

tert-butyl-diphenylsilyl

TEA

triethylamine

THF

tetrahydrofurane

TMS

trimethylsilyl

Z

benzyloxycarbonyl

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Midland MM, Nguyen NH (1981) J. Org. Chem. 46: 4107Google Scholar
  2. 2.
    Crossley R (1992) Tetrahedron 48: 8155Google Scholar
  3. 3.
    Jones JB, Sih CJ, Perlman D (eds) (1981) Applications of biochemical systems in organic chemistry. Wiley, New YorkGoogle Scholar
  4. 4.
    Porter R, Clark S (eds) (1985) Enzymes in organic synthesis. Ciba Foundation Symposium 111. Pitman, LondonGoogle Scholar
  5. 5.
    Davies HG, Green RH, Kelly DR, Roberts SM (eds) (1989) Biotransformations in preparative organic chemistry. Academic Press, LondonGoogle Scholar
  6. 6.
    Abramowicz DA (ed) (1990) Biocatalysis. Van Nostrand Reinhold, New York.Google Scholar
  7. 7.
    Whitesides GM, Wong C-H (1985) Angew, Chem. Int. Ed. Engl. 24: 617.Google Scholar
  8. 8.
    Jones JB (1986) Tetrahedron 42: 3351.Google Scholar
  9. 9.
    Yamada H, Shimizu S (1988) Angew, Chem. Int. Ed. Engl. 27: 622Google Scholar
  10. 10.
    Wong C-H (1989) Science 244: 1145Google Scholar
  11. 11.
    Zhu L-M, Tedford MC (1990) Tetrahedron 46: 6587Google Scholar
  12. 12.
    Xie X-F (1991) Tetrhedron Asymmetry 2: 733Google Scholar
  13. 13.
    Boland W, Frobl C, Lorenz M (1991) Synthesis 1049Google Scholar
  14. 14.
    Santaniello E, Ferraboschi P, Grisenti P, Manzocchi A (1992) Chem. Rev. 92: 1071Google Scholar
  15. 15.
    Faber K, Franssen MCR (1993) TIBTECH 11: 461Google Scholar
  16. 16.
    Chen C-S, Sih CJ (1989) Angew. Chem. Int. Ed. Engl. 28: 695Google Scholar
  17. 17.
    Dordick JS (1989) Enzyme Microb. Technol. 11: 194Google Scholar
  18. 18.
    Klibanov AM (1990) Acc. Chem. Res. 23: 114Google Scholar
  19. 19.
    Margolin AL (1991) CHEMTECH 160Google Scholar
  20. 20.
    Faber K, Riva S (1992) Synthesis 895Google Scholar
  21. 21.
    Zaks A, Klibanov AM (1984) Science 224: 1249Google Scholar
  22. 22.
    Aldercreutz P., Mattiasson B (1987) Biocatalysis 1: 99Google Scholar
  23. 23.
    Inagaki M, Hiratake J, nishioka, T, Oda J (1991) J. Am. Chem. Soc. 113: 9360Google Scholar
  24. 24.
    Zaks A, Klibanov AM (1986) J. Am. Chem. Soc. 108: 2767Google Scholar
  25. 25.
    Russel AJ, Klibanov AM (1988) J. Biol. Chem 263: 11624Google Scholar
  26. 26.
    Sakurai T, Margolin AL, Klibanov AM (1988) J. Am. Chem. Soc. 110: 7236Google Scholar
  27. 27.
    Kitaguchi H, Fitzpatrick PA, Huber JE, Klibanov AM (1989) J. Am. Chem. Soc. 111: 3094Google Scholar
  28. 28.
    Klibanov AM (1986) CHEMTECH 16: 354Google Scholar
  29. 29.
    Huang FC, Lee LFH, Mittal RSD, Ravi Kumar PR, Chan JA, Sih CJ, Sih CJ, Caspi E, Eck CR (1975) J. Am. Chem. Soc. 97: 4144Google Scholar
  30. 30.
    Ramos Tombo GM, Schar H-P, Fernandez X, Busquets I Ghisalba O (1986) Tetrahedron Lett. 27: 5707Google Scholar
  31. 31.
    Janssen AJM, Klunder AJH, Zwanenburg BZ (1991) Tetrahedron 47: 7645Google Scholar
  32. 32.
    Zaks A, Klibanov AM (1985) Proc. Natl. Acad., Sci. USA 82: 3192Google Scholar
  33. 33.
    Chen C-S, Fujimoto Y, Girdaukas G, Sih CJ (1982) J. Am. Chem. Soc. 104: 7294Google Scholar
  34. 34.
    Therisod M, Klibanov AM (1986) J. Am. Chem. Soc. 108: 5638Google Scholar
  35. 35.
    Ghogare A, Kumar GS (1989) J. Chem. Soc., Chem. Commun. 1533Google Scholar
  36. 36.
    Bianchi D, Cesti P, Battistel E (1988) J. Org. Chem. 53: 5531Google Scholar
  37. 37.
    Sweers HM, Wong CH (1986) J. Am. Chem. Soc. 108: 6421Google Scholar
  38. 38.
    Wang Y-F, Lalonde JJ, Momongan M, Bergbreiter DE, Wong C-H (1988) J. Am. Chem. Soc. 110: 7200Google Scholar
  39. 39.
    Drueckhammer DG, Hennen WJ, Pederson RL, Barbas CF, Gautheron CM, Krach T, Wong C-H (1991) Synthesis 499Google Scholar
  40. 40.
    Baer E, Maurukas J, Russel MJ (1952) J. Am. Chem. Soc. 74: 152Google Scholar
  41. 41.
    Suemune H, Mizuhara Y, Akita H, Sakai K (1986) Chem. Pharm. Bull. 34: 3440Google Scholar
  42. 42.
    Hirth G, Barner R (1982) Helv. Chim. Acta 65: 1059Google Scholar
  43. 43.
    Chandrakumar NS, Hajdu J (1983) J. Org. Chem. 48: 1197Google Scholar
  44. 44.
    Morishima H, Koike Y, Nakano M, Atsuumi S, Tanaka S, Funabashi H, Hashimoto J, Sawasaki Y, Mino N, Nakano K, Matsushima K, Nakamuchi K, Yano M (1989) Biochem. Biophys. Res. Commun. 159: 999Google Scholar
  45. 45.
    Kojke K, Numata M, Sugikoto M, Nakahara Y, Ogawa T (1986) Carbohydr. Res. 113Google Scholar
  46. 46.
    Tsuji K, Terao Y, Achiwa K (1989) Tetrahedron Lett. 30: 6189Google Scholar
  47. 47.
    Atsuumi S, Nakano M, Koide Y, Tanaka S, Ohkubo M, Yonezawa T, Funabashi H, Hashimoto J, Morishima H (1990) Tetrahedron Lett. 31: 1601.Google Scholar
  48. 48.
    Bianchi D, Cesti P, Golini P, Spezia S, Garavaglia C, Mirenna L, (1992) Pure Appl. Chem. 64:1073Google Scholar
  49. 49.
    Barnett CJ, Wilson TM (1989) Tetrahedron Lett. 30: 6291Google Scholar
  50. 50.
    Wang Y-F, Wong, C-H (1988) J. Org. Chem. 53: 3127Google Scholar
  51. 51.
    Terao Y, Murata M, Achiwa K, Nishio T, Akamtsu M, Kamimura M (1988) Tetrahedron Lett. 29: 5173Google Scholar
  52. 52.
    Santanello E, Feraboschi P, Griesenti P, (1990) Tetrahedron Lett. 31: 5657Google Scholar
  53. 53.
    Djerourou A-H, Blanco L (1991) Tetrahedron Lett. 32: 6325Google Scholar
  54. 54.
    Naemura K, Furutani A (1991) J. Chem. Soc., Perkin Trans. 1: 2891Google Scholar
  55. 55.
    Hirose Y, Kariya K, Sasaki I, Kurono I, Ebiike H, Achiwa K (1992) Tetrahedron Lett. 33: 7157Google Scholar
  56. 56.
    Holdgrun XK, Sih CJ (1991) Tetrahedron Lett. 32: 3465Google Scholar
  57. 57.
    Yamamoto K, Nishioka T, Oda J, Yamamoto Y (1988) Tetrahedron Lett. 29: 1717Google Scholar
  58. 58.
    Yamamoto Y, Iwasa M, Sawada S, Oda J (1990) J. Agric. Biol. Chem. 54: 3269Google Scholar
  59. 59.
    Murata M, Achiwa K (1991) Tetrahedron Lett. 32: 6763Google Scholar
  60. 60.
    Gutman AL, Zuobi K, Bravdo T (1990) J. Org. Chem. 55: 3546Google Scholar
  61. 61.
    Gutman AL, Bravdo T (1989) J. Org. Chem. 54: 4263Google Scholar
  62. 62.
    Gao J, Jorgensen WL (1990) Chemtracts-Organic Chemistry3: 244Google Scholar
  63. 63.
    Bjorkling F, Boutelje J, Gatenbeck S Hult K, Norin T, Szmulik P (1985) Tetrahedron 41: 1347Google Scholar
  64. 64.
    Luyten M, Muller S, Herzog B, Keese R (1987) Helv. Chim. Acta 70: 1250Google Scholar
  65. 65.
    Toone EJ, Jones JB (1991) Tetrahedron Asymmetry 2: 1041Google Scholar
  66. 66.
    Gutman AL, Shapira M, Boltanski A (1992) J. Org. Chem. 57: 1063Google Scholar
  67. 67.
    Shapira M, Gutman AL (1994) Tetrahedron Asymmetry 5: 1689Google Scholar
  68. 68.
    Gutman AL, Bravdo T (1989) J. Org. Chem. 54: 5645Google Scholar
  69. 69.
    Theil F, Schick H, Winter G, Reck G (1991) Tetrahedron 47: 7569Google Scholar
  70. 70.
    Harris KJ, Gu Q-M, Shih Y-E, Girdaukas G, Sih CJ (1991) Tetrahedron Lett. 32: 3941Google Scholar
  71. 71.
    Johnson CR, Bis SJ (1992) Tetrahedron Lett. 33: 7287Google Scholar
  72. 72.
    Johnson CR, Golebiowski A, McGill TK, Steensma DH (1991) Tetrahedron Lett. 32: 2597Google Scholar
  73. 73.
    Ader U, Breitgoff D, Klein P, Laumen KE, Schneider MP (1989) Tetrahedron Lett. 30: 1793Google Scholar
  74. 74.
    Bonini C, Racioppi R, Viggiani L, Righi G, Rossi L (1993) Tetrahedron Asymmetry, 4: 793Google Scholar
  75. 75.
    Bonini C, Racioppi R, Righi G, Viggiani L (1993) J. Org. Chem. 58: 802Google Scholar
  76. 76.
    Pottie M. Van der Eycken J, Vandewalle M (1991) Tetrahedron Asymmetry 2: 239Google Scholar
  77. 77.
    Tanaka M, Yoshioka M, Sakai K (1993) Tetrahedron Asymmetry 4: 981Google Scholar
  78. 78.
    Toyooka N, Nishino A, Mamose T (1993) Tetrahedron Lett. 34: 4539Google Scholar
  79. 79.
    Takano S, Moriya M, Higashi Y, Ogasawara K, (1993) J. Chem. Soc., Chem. Commun. 177Google Scholar
  80. 80.
    Andreu C, Macro JA, Asensio G (1990) J. Chem. Soc., Perkin Trans. 1: 3209Google Scholar
  81. 81.
    Theil F, Ballschuh S, Schick H, Haupt M, Hafner B, Schwarz S (1988) Synthesis 540Google Scholar
  82. 82.
    Sugai T, Mori K (1988) Synthesis 19Google Scholar
  83. 83.
    Theil F, Kunath A, Schick H (1992) 33: 3457Google Scholar
  84. 84.
    Hemmerle H, Gais HJ (1987) Tetrahedron Lett. 28: 3471Google Scholar
  85. 85.
    Momose T, Toyooka N, Jin M (1992) Tetrahedron Lett. 33: 5389Google Scholar
  86. 86.
    Vanttinen E, Kanerva LT (1992) Tetrahedron Asymmetry 3: 1529Google Scholar
  87. 87.
    Sato M, Ohuchi H, Abe Y, Kaneko C (1992) Tetrahedron Asymmetry 3: 313Google Scholar
  88. 88.
    Bis SJ, Whitaker DT, Johnson CR (1993) Tetrahedron Asymmetry 4: 875Google Scholar
  89. 89.
    Nicolosi G, Morrone R, Patti A, Piattelli M (1992) Tetrahedron Asymmetry 3: 753Google Scholar
  90. 90.
    Howell JAS, Palin MG, Jaouen G, Top S, El Hafa H, Cense JM (1993) Tetrahedron Asymmetry 3: 1241Google Scholar
  91. 91.
    Fuji K, Kawabata T, Kiryu Y, Sugiura Y (1990) Tetrahedron Lett. 31: 6663Google Scholar
  92. 92.
    Ozegowski R, Kunath A, Schick H (1993) Tetrahedron Asymmetry 4: 695Google Scholar
  93. 93.
    Kagan HB (1985) Chiral ligands for asymmetric catalysis. In: Morrison JD (ed) Asymmetric synthesis, Vol. 5, Academic, Orlando, p 1Google Scholar
  94. 94.
    Gotor V, Memendez E, Mouloungui Z, Gaset A (1993) J. Chem. Soc., Perkin Trans. 1: 2453Google Scholar
  95. 95.
    Pozo M, Gotor V (1993) Tetrahedron 49: 4321Google Scholar
  96. 96.
    Puertas S, Brieva R, Rebolledo F, Gotor V (1993) Tetrahedron 49: 4007Google Scholar
  97. 97.
    Margolin AL, Fitzpatrick PA, Dubin PL, Klibanov AM (1991) J. Am. Chem. Soc. 113: 4693Google Scholar
  98. 98.
    Gutman AL, Meyer E, Kalerin E, Polyak F, Sterling J (1992) Biotechnol. Bioeng. 40: 760Google Scholar
  99. 99.
    Asensio G, Andreu C, Macro JA (1991) Tetrahedron Lett. 32: 4197Google Scholar
  100. 100.
    Fernandez S, Brieva R, Rebolledo F, Gotor V (1992) J. Chem. Soc., Perkin Trans. 1: 2885Google Scholar
  101. 101.
    Bevinakatti HS, Newadkar R (1990) Tetrahedron Asymmetry 1: 583Google Scholar
  102. 102.
    Cambou B, Klibanov AM (1985) Biotechnol. Bioeng. 26: 1449Google Scholar
  103. 103.
    Kirchner G, Scollar MP, Klibanov AM (1985) J. Am. Chem. Soc. 107: 7072Google Scholar
  104. 104.
    Engel KH (1991) Tetrahedron Asymmetry 2: 165Google Scholar
  105. 105.
    Berglund P, Holmquist M, Hedenstrom E, Hult K, Hogberg HE (1993) Tetrahedron Asymmetry 4: 1869Google Scholar
  106. 106.
    Chen C-S, Wu S-H, Girdaukas G, Sih CJ (1987) J. Am. Chem. Soc. 109: 2812Google Scholar
  107. 107.
    Fukui T, Kawamoto T, Sonomoto K, Tanaka A (1990) Appl. Microbiol. Biotechnol. 34: 330Google Scholar
  108. 108.
    Macfarlane ELA, Roberts SM, Steukers VGR, Taylor RL (1993) J. Chem. Soc., Perkin Trans. 1: 2287Google Scholar
  109. 109.
    Delinck DL, Margolin AL (1990) Tetrahedron Lett. 31: 6797Google Scholar
  110. 110.
    Ferraboschi P, Grisenti P, Manzocchi A, Santaniello E (1990) J. Org. Chem. 55: 6241Google Scholar
  111. 111.
    Grisenti P, Ferraboschi P, Manzocchi A, Santaniello E (1992) Tetrahedron 48: 3827Google Scholar
  112. 112.
    Lentz N, Peet N (1990) Tetrahedron Lett. 31: 811Google Scholar
  113. 113.
    Bevinakatti HS, Newadkar RV (1993) Tetrahedron Asymmetry 4: 773Google Scholar
  114. 114.
    Kanerva LT, Vanttinen E (1993) Tetrahedron Asymmetry 4: 85Google Scholar
  115. 115.
    Bianchi D, Cabri W, Cesti P, Francalanci F, Rama F (1988) Tetrahedron Lett. 29: 2455Google Scholar
  116. 116.
    Ferraboschi P, Casati S, Grisenti P, Santaniello E (1993) Tetrahedron Asymmetry 4: 9Google Scholar
  117. 117.
    Jouglet B, Rousseau G (1993) Tetrahedron Lett. 34: 2307Google Scholar
  118. 118.(a)
    Ennis MD, Old DW (1992) Tetrahedron Lett. 33: 6283Google Scholar
  119. 118.(b)
    Ennis MD, Ghazal NB (1992) Tetrahedron Lett. 33: 6287Google Scholar
  120. 119.
    Antus S, Gottsegen A, Kajtar J, Kovasc T, Toth TS, Wagner H (1993) Tetrahedron Asymmetry, 4: 339Google Scholar
  121. 120.
    Herradon B (1992) Tetrahedron Asymmetry 3 209Google Scholar
  122. 121.
    Janssen AJM, Klunder AJH, Zwanenburg B (1991) Tetrahedron 47: 5513Google Scholar
  123. 122.
    Morgan B, Oehlschlager AC, Stokes TM (1991) Tetrahedron 47: 1611Google Scholar
  124. 123.
    Frykman H, Ohrner N, Norin T, Hult K (1993) Tetrahedron Lett. 34: 1367Google Scholar
  125. 124.
    Hult K, Norin T (1992) Pure Appl. Chem. 64: 1129Google Scholar
  126. 125.
    Belan A, Bolte J, Fauvé A, Gourcy JG, Veschambre H (1987) J. Org. Chem. 52: 256Google Scholar
  127. 126.
    Stokes TM, Oehlschlager AC (1987) Tetrahedron Lett. 28: 2091Google Scholar
  128. 127.
    Gutman AL, Brenner D, Boltanski A (1993) Tetrahedron Asymmetry 4: 839Google Scholar
  129. 128.
    Laumen K, Brietgoff D, Schneider MP (1988) J. Chem. Soc., Chem. Commun. 1459Google Scholar
  130. 129.
    Morgan B, Oehlschlager AC, Stokes TM (1992) J. Org. Chem. 57: 3231Google Scholar
  131. 130.
    Hsu S-H, Wu S-S, Wang Y-F, Wong C-H (1990) Tetrahedron Lett. 31: 6403Google Scholar
  132. 131.
    Nieduzak TR, Margolin AL (1991) Tetrahedron Asymmetry 2: 113Google Scholar
  133. 132.
    Izumi T, Fukaya K (1993) Bull. Chem. Soc. Jpn. 66: 1216Google Scholar
  134. 133.
    Hiratake J, Inagaki M, Nishioka T, Oda (1988) J. Org. Chem. 53: 6130Google Scholar
  135. 134.
    Ader A, Schneider MP (1992) Tetrahedron Asymmetry 3: 521Google Scholar
  136. 135.
    Bevinakatti HS, Banjeri AA (1992) J. Org. Chem. 57: 6003Google Scholar
  137. 136.
    Kim M-J, Choi YK (1992) J. Org. Chem. 57: 1605Google Scholar
  138. 137.
    Chen C-S, Liu Y-C, Marsella MJ (1990) J. Chem. Soc., Perkin 1 2559Google Scholar
  139. 138.
    Sakaki J-I, Sakoda H, Sugita Y, Sato M, Kaneko C (1991) Tetrahedron Asymmetry 2: 343Google Scholar
  140. 139.
    Georgens U, Schneider MP (1991) J. Chem. Soc., Chem. Commun. 1064Google Scholar
  141. 140.
    Georgens U, Schneider MP (1991) J. Chem. Soc., Chem. Commun. 1066Google Scholar
  142. 141.
    Chong JM, Mar EK (1991) Tetrahedron Lett. 32: 5683Google Scholar
  143. 142.
    Katsuki T, Sharpless KB (1980) J. Am. Chem. Soc. 102: 5974Google Scholar
  144. 143.
    Carlier PR, Mungall WS, Schroder G, Sharpless KB (1988) J. Am. Chem. Soc. 110: 2978Google Scholar
  145. 144.
    Burgess K, Jennings LD (1990) J. Am. Chem. Soc. 112: 7434Google Scholar
  146. 145.
    Burgess K, Jennings LD (1991) J. Am. Chem. Soc. 113: 6129Google Scholar
  147. 146.
    Burgess K, Jennings LD (1990) J. Org. Chem. 55: 1138Google Scholar
  148. 147.
    Bornscheuer U, Schapohler S, Scheper T, Schugerl K (1991) Tetrahedron Asymmetry 2: 1011Google Scholar
  149. 148.
    Burgess K, Henderson I (1990) Tetrahedron Asymmetry 1: 57Google Scholar
  150. 149.
    Carretero JC, Dominguez E (1992) J. Org. Chem. 57: 3867Google Scholar
  151. 150.
    Carretero JC, Dominguez E (1993) J. Org. Chem. 58: 1596Google Scholar
  152. 151.
    Sparks MA, Panek JS (1991) Tetrahedron Lett. 32: 4085Google Scholar
  153. 152.
    Gil G, Ferre E, Meou A, Petit JL, Triantaphylides C (1987) Tetrahedron Lett. 28: 1647Google Scholar
  154. 153.
    Langrand G, Secchi M, Buono G, Baratti J, Triantaphylides C (1985) Tetrahedron Lett. 26: 1857Google Scholar
  155. 154.
    Laumen K, Seemayer R, Schneider MP (1990) J. Chem. Soc., Chem. Commun. 49Google Scholar
  156. 155.
    Berkowitz DB, Danishefsky SJ (1991) Tetrahedron Lett. 32: 5497Google Scholar
  157. 156.
    Berger B, Faber K (1991) J. Chem. Soc., Chem. Commun. 1198Google Scholar
  158. 157.
    Evans CT, Roberts SM, Shoberu KA, Sutherland AG (1992) J. Chem. Soc., Perkin Trans. 1 589Google Scholar
  159. 158.
    Takano S, Suzuki M, Ogasawara K (1993) Tetrahedron Asymmetry 4: 1043Google Scholar
  160. 159.
    McCague R, Olive HF, Roberts SM (1993) Tetrahedron Lett. 34: 3785Google Scholar
  161. 160.
    Cotterill IC, Sutherland AG, Roberts SM, Grobbauer R, Spreitz J, Faber K (1991) J. Chem. Soc., Perkin Trans. 1 1365Google Scholar
  162. 161.
    Cregge RJ, Wagner ER, Freedman J, Margolin AL (1990) J. Org. Chem. 55: 4237Google Scholar
  163. 162.
    Ling L, Watanabe Y, Akiyama T, Ozaki S (1992) Tetrahedron Lett. 33: 1911Google Scholar
  164. 163.
    Seemayer R, Schneider MP (1991) J. Chem. Soc., Chem. Commun. 49Google Scholar
  165. 164.
    Caron G, Kazlauskas RJ (1993) Tetrahedron Asymmetry 4: 1995Google Scholar
  166. 165.
    Mattson A, Ohrner N, Hult K, Norin T (1993) Tetrahedron Asymmetry 4: 925Google Scholar
  167. 166.
    Bisht KS, Parmar VS, Crout DHG (1993) Tetrahedron Asymmetry 4: 957Google Scholar
  168. 167.
    Nakamura K, Ishihara K, Ohno A, Uemura M, Nishimura H, Hayashi Y (1990) Tetrahedron Lett. 31: 3603Google Scholar
  169. 168.
    Yamazaki Y, Hosono K (1990) Tetrahedron Lett. 31: 3895Google Scholar
  170. 169.
    Baldoli C, Maiorana S, Carrea G, Riva S (1993) Tetrahedron Asymmetry 4: 767Google Scholar
  171. 170.
    Boaz NW (1989) Tetrahedron Lett. 30: 2061Google Scholar
  172. 171.
    Effenberger F, Ziegler T, Forster S (1987) Angew. Chem. Int. Ed. Engl. 26: 458Google Scholar
  173. 172.
    Ohta H, Miyamae Y, Tsuchihashi G (1986) J. Agric. Biol. Chem. 50: 3181Google Scholar
  174. 173.
    Wang Y-F, Chen S-T, Liu KK-C, Wong C-H (1989) Tetrahedron Lett. 30: 1917Google Scholar
  175. 174.
    Inagaki M, Hiratake J, Nishioka T, Oda J (1992) J. Org. Chem. 57: 5643Google Scholar
  176. 175.
    Inagaki M, Hiratake J, Nishioka T, Oda J (1989) J. Agric. Biol. Chem. 53: 1879Google Scholar
  177. 176.
    Lin G, Liu S-H, Chen S-J, Wu F-C, Sun H-L (1993) Tetrahedron Lett. 34: 6057Google Scholar
  178. 177.
    Kamal H, Damayanthi Y, Rao MV (1992) Tetrahedron Asymmetry 3: 1361Google Scholar
  179. 178.
    Wallase JS, Reda KB, Williams ME, Morrow CJ (1990) J. Org. Chem. 55: 3544Google Scholar
  180. 179.
    Gou D-M, Liu Y-C, Chen C-S (1993). J. Org. Chem. 58: 1287Google Scholar
  181. 180.
    Kanerva LT, Sundholm O (1993) J. Chem. Soc., Perkin Trans. 1 1385Google Scholar
  182. 181.
    Burgess K, Henderson I, Ho K-K (1992) J. Org. Chem. 57: 1290Google Scholar
  183. 182.
    Pirke WH, Sikkenga DL, Pavlin MS (1989) Chem. Rev. 89: 347Google Scholar
  184. 183.
    Shkolnik E, Gutman AL (1994) Bioorg. & Medicinal Chem. 2: 567Google Scholar
  185. 184.
    Bevinakatti HS, Banjeri AA (1991) J. Org. Chem. 56: 5372Google Scholar
  186. 185.
    Lu Y, Miet C, Kunesch N, Poisson JE (1993) Tetrahedron Asymmetry 4: 893Google Scholar
  187. 186.
    Bevinakatti HS, Banjeri AA, Newadkar RV (1989) J. Org. Chem. 54: 2453Google Scholar
  188. 187.
    Bianchi D, Cesti P (1990) J. Org. Chem. 55: 5657Google Scholar
  189. 188.
    Barnier JP, Blanco L, Rousseau G, Guibe-Jampel E, Fressel I (1993) J. Org. Chem. 58: 1570Google Scholar
  190. 189.
    Quiros M, Sanchez VM, Brieva R, Rebolledo F, Gotor V (1993) Tetrahedron Asymmetry 4: 1105Google Scholar
  191. 190.
    Gotor V, Brieva R, Gonzalez, Rebolledo F (1991) Tetrahedron 47: 9207Google Scholar
  192. 191.
    Crich JZ, Brieva R, Marquart P, Gu R-L, Flemming S, Sih CJ (1993) J. Org. Chem. 58: 3252Google Scholar
  193. 192.
    Bevinakatti HS, Newadkar RV, Banjeri AA (1990) J. Chem. Soc., Chem. Commun. 1091Google Scholar
  194. 193.
    Brieva R, Crich JZ, Sih CJ (1993) J. Org. Chem. 58: 1068Google Scholar
  195. 194.
    Hiratake J, Yamamoto K, Yamamoto Y, Oda J (1989) Tetrahedron Lett. 30: 1555Google Scholar
  196. 195.
    Gutman AL, Oren D, Boltanski A, Bravdo T (1987) Tetrahedron Lett. 28: 3861Google Scholar
  197. 196.
    Gutman AL, Zuobi K, Boltanski A (1987) Tetrahedron Lett. 28: 5367Google Scholar
  198. 197.
    Huffer M, Schreier P (1991) Tetrahedron Asymmetry 2: 1157Google Scholar
  199. 198.
    Sugai T, Ohsawa S, Yamada H, Ohta H (1990) Synthesis 1112Google Scholar
  200. 199.
    Bonini C, Pucci P, Racioppi R, Viggiani L (1992) Tetrahedron Asymmetry 3: 29Google Scholar
  201. 200.
    Henkel B, Kunath A, Schick H (1993) Tetrahedron Asymmetry 4: 153Google Scholar
  202. 201.
    Makita A, Nihira T, Yamada Y (1987) Tetrahedron Lett. 28: 805Google Scholar
  203. 202.
    Yamada H, Ohsawa S, Sugai T, Ohta H, Yoshikawa S (1989) Chem. Lett. 1775.Google Scholar
  204. 203.
    Zhi-wei G, Ngooi TK, Scilimati A, Fulling G, Sih CJ(1988) Tetrahedron Lett. 29: 5583Google Scholar
  205. 204.
    Lobell M, Schneider MP (1993) Tetrahedron Asymmetry 4: 1027Google Scholar
  206. 205.
    Zhi-wei G, Sih CJ (1988) J. Am. Chem. Soc. 110: 1999Google Scholar
  207. 206.
    Margolin, AL, Crenne J-Y, Klibanov AM (1987) Tetrahedron Lett. 28: 1607Google Scholar
  208. 207.
    O'Hagan D, Zaidi NA (1993) J. Chem. Soc., Perkin Trans. 1 2389Google Scholar
  209. 208.
    Gutman AL, Meyer E, Yue X, Abell C (1992) Tetrahedron Lett. 33: 3943Google Scholar
  210. 209.
    Cesti P, Zaks A, Klibanov AM (1985) Appl. Biochem. Biotechnol 11: 401Google Scholar
  211. 210.
    Parmar VS, Sinha R, Bisht KS, Gupta S, Prasad AK, Taneja P (1993) Tetrahedron 49: 4107Google Scholar
  212. 211.
    Janssen AJM, Klunder AJH, Zwanenburg B (1991) Tetrahedron 47: 7409Google Scholar
  213. 212.
    Ramaswamy S, Morgan B, Oehlschlager AC (1990) Tetrahedron Lett. 31: 3405Google Scholar
  214. 213.
    Ottolina G, Carrea G, Riva S (1990) J. Org. Chem. 55: 2366Google Scholar
  215. 214.
    Theil F, Weidner J, Ballschuh S, Kunath A, Schick H (1993) Tetrahedron Lett. 34: 305Google Scholar
  216. 215.
    Wang Y-F, Dumas DP, Wong C-H (1993) Tetrahedron Lett. 34: 403Google Scholar
  217. 216.
    Pedrocchi-Fantoni G, Servi S (1992) J. Chem. Soc., Perkin Trans 1 1029Google Scholar
  218. 217.
    Chinsky N, Margolin AL, Klibanov AM (1989) J. Am. Chem. Soc. 111: 386Google Scholar
  219. 218.
    Bovara R, Carrea G, Ferrara L, Riva S (1991) Tetrahedron Asymmetry 2: 931Google Scholar
  220. 219.
    Nicolosi G, Piattelli M, Sanfilippo C (1993) Tetrahedron 49: 3143Google Scholar
  221. 220.
    Parmar VS, Prasad AK, Sharma NK, Singh SK, Pati HN, Gupta S (1992) Tetrahedron 48: 6495Google Scholar
  222. 221.
    Natoli M, Nicolosi G, Piattelli M (1992) J. Org. Chem. 57: 5776Google Scholar
  223. 222.
    Parmar VS, Prasad AK, Sharma NK, Vardhan A, Pati HN, Sharma SK, Bisht KS (1993) J. Chem. Soc., Chem. Commun. 27Google Scholar
  224. 223.
    Hennen WJ, Sweers HM, Wang Y-F, Wong C-H (1988) J. Org. Chem. 53: 4939Google Scholar
  225. 224.
    Bjorkling F, Godtfredsen SE, Kirk O (1989) J. Chem. Soc., Chem. commun. 934Google Scholar
  226. 225.
    Therisod M, Klibanov AM (1987) J. Am. Chem. Soc. 109: 3977Google Scholar
  227. 226.
    Nicotra F, Riva S, Secundo F, Zucchelli L (1989) Tetrahedron Lett. 30: 1703Google Scholar
  228. 227.
    Ciuffreda P, Colombo D, Ronchetti F, Toma L (1990) J. Org. Chem. 55: 4187Google Scholar
  229. 228.
    Riva S, Chopineau J, Kieboom APG, Klibanov AM (1988) J. Am. Chem. Soc. 110: 584Google Scholar
  230. 229.
    Carrea G, Riva S, Secundo F, Danieli B (1989) J. Chem. Soc., Perkin Trans. 1: 1057Google Scholar
  231. 230.
    Danieli B, De Bellis P, Carrea G, Riva S (1990) Helv. Chim. Acta 73: 1837Google Scholar
  232. 231.
    Chinn MJ, Lacazio G, Spackman DG, Turner NJ, Roberts SM (1992) J. Chem. Soc., Perkin Trans. 1: 661Google Scholar
  233. 232.
    Panza L, Brasca S, Riva S, Russo G (1993) Tetrahedron Asymmetry 4: 931Google Scholar
  234. 233.
    Lacazio G, Roberts SM (1993) J. Chem. Soc., Perkin Trans. 1: 1099Google Scholar
  235. 234.
    Wong C-H, Chen S-T, Hennen WJ, Bibbs JA, Wang Y-F, Liu JL-C, Pantoliano MW, Whitlow M, Bryan PN (1990) J. Am. Chem. Soc. 112: 945Google Scholar
  236. 235.
    Moris F, Gotor V (1993) J. Org. Chem. 58: 653Google Scholar
  237. 236.
    Garcia-Alles LF, Moris F, Gotor V (1993) Tetrahedron Lett. 34: 6337Google Scholar
  238. 237.
    Riva S, Bovara R, Ottolina G, Secundo F, Carrea G (1989) J. Org. Chem. 54 3161Google Scholar
  239. 238.
    Riva S, Klibanov AM (1988) J. Am. Chem. Soc. 110: 3291Google Scholar
  240. 239.
    Njar VCO, Caspi E (1987) Tetrahedron Lett. 28: 6549Google Scholar
  241. 240.
    Ottolina G, Carrea G, Riva S (1991) Biocatalysis 5: 131Google Scholar
  242. 241.
    Margolin AL, Delinck DL, Whalon MR (1990) J. Am. Chem. Soc. 112: 2849Google Scholar
  243. 242.
    Delinck DL, Margolin AL (1990) Tetrahedron Lett. 31: 3093Google Scholar
  244. 243.
    Holla EW (1989) Angew. Chem. Int. Ed. Engl. 28: 220Google Scholar
  245. 244.
    Ling L, Ozaki S (1993) Tetrahedron Lett. 34: 2501Google Scholar
  246. 245.
    Henly R, Elie CJJ, Buser HP, Ramos G, Moser HE (1993) Tetrahedron Lett. 34: 2923Google Scholar
  247. 246.
    Lutz D, Guldner A, Thums R, Schreier P (1990) Tetrahedron Lett. 1: 783Google Scholar
  248. 247.
    Morgan B, Oehlschlager AC (1993) Tetrahedron Asymmetry 4: 907Google Scholar
  249. 248.
    Fourneron JD, Chiche M, Pieroni G (1990) Tetrahedron Lett. 31: 4875Google Scholar
  250. 249.
    Geresh S, Elbaz E, Glaser R (1993) Tetrahedron 49: 4939Google Scholar
  251. 250.
    Laane C, Boeren S, Vos K, Veeger C (1987) Biotechnol. Bioeng. 30: 81Google Scholar
  252. 251.
    Zaks A, Klibanov AM (1988) J. Biol. Chem 263: 3194Google Scholar
  253. 252.
    Parida S, Dordiok JS (1991) J. Am. Chem. Soc. 113: 2253Google Scholar
  254. 253.
    Bornscheuer U, Herar A, Kreye L, Wendel V, Capewell A, Meyer HH, Scheper T, Kolisis FN (1993) Tetrahedron Asymmetry 4: 1007Google Scholar
  255. 254.
    Parida S, Dordick JS (1993) J. Org. Chem. 58: 3238Google Scholar
  256. 255.
    Kanerva LT, Vihanto J, Halme MH, Loponen JM, Euranto EK (1990) Acta Chem. Scand. 44: 1032Google Scholar
  257. 256.
    Secundo F, Riva S, Carrea G (1992) Tetrahedron Asymmetry 3: 267Google Scholar
  258. 257.
    Zaks A, Klibanov AM (1988) J. Biol. Chem. 263: 8017Google Scholar
  259. 258.
    Kitaguchi H, Itoh I, Ono M (1990) Chem. Lett. 1203Google Scholar
  260. 259.
    Gutman AL, Shapira M (1991) J. Chem. Soc., Chem. Commun. 1467Google Scholar
  261. 260.
    Adlercreutz P (1991) Eur. J. Biochem. 199: 609Google Scholar
  262. 261.
    Sanchez-Montero JM, Hamon V, Thomas D, Legoy MD (1991) Biochem. Biophys. Acta 1078: 345Google Scholar
  263. 262.
    Kvittingen, L, Sjursnes B, Anthosen T, Halling P (1992) Tetrahedron 48: 2793Google Scholar
  264. 263.
    Yamamoto Y, Kise H (1993) Chem. Lett. 1821Google Scholar
  265. 264.
    Wescott CR, Klibanov AM (1993) J. Am. Chem. Soc. 115: 1629Google Scholar
  266. 265.
    Westcott CR, Klibanov AM (1993) J. Am. Chem. Soc. 115: 10362Google Scholar
  267. 266.
    Terradas F, Teston-Henry M, Fitzpatrick PA, Klibanov AM (1993) J. Am. Chem. Soc. 115: 390Google Scholar
  268. 267.
    Tawaki S, Klibanov AM (1992) J. Am. Chem. Soc. 114: 1882Google Scholar
  269. 268.
    Fitzpatrick PA, Klibanov AM (1991) J. Am. Chem. Soc. 113: 3166Google Scholar
  270. 269.
    Nakamura K, Takebe Y, Kitayama T, Ohno A (1991) Tetrahedron Lett. 32: 4941Google Scholar
  271. 270.
    Ueji S, Fujino R, Okubo N, Miyazawa T, Kurita S, Kitadani M, Muromatsu A (1992) Biotechnol. Lett. 14: 163Google Scholar
  272. 271.
    Rubio E, Fernandez-Mayorales A, Klibanov AM (1991) J. Am. Chem. Soc. 113: 695Google Scholar

Copyright information

© Springer-Verlag 1995

Authors and Affiliations

  • A. L. Gutman
    • 1
  • M. Shapira
    • 1
  1. 1.Department of ChemistryTechnion-Israel Institute of TechnologyHaifaIsrael

Personalised recommendations