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New alcohol dehydrogenases for the synthesis of chiral compounds

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New Enzymes for Organic Synthesis

Part of the book series: Advances in Biochemical Engineering/Biotechnology ((4143,volume 58))

Abstract

The enantioselective reduction of carbonyl groups is of interest for the production of various chiral compounds such as hydroxy acids, amino acids, hydroxy esters, or alcohols. Such products have high economic value and are most interesting as additives for food and feed or as building blocks for organic synthesis. Enzymatic reactions or biotransformations with whole cells (growning or resting) for this purpose are described. Although conversions with whole cells are advantageous with respect to saving expensive isolation of the desired enzymes, the products often lack high enantiomeric excess and the process results in low time-space-yield. For the synthesis of chiral alcohols, only lab-scale syntheses with commercially available alcohol dehydrogenases have been described yet. However, most of these enzymes are of limited use for technical applications because they lack substrate specificity, stability (yeast ADH) or enantioselectivity (Thermoanaerobium brockii ADH). Furthermore, all enzymes so far described are forming (S)-alcohols. Quite recently, we found and characterized several new bacterial alcohol dehydrogenases, which are suited for the preparation of chiral alcohols as well as for hydroxy esters in technical scale. Remarkably, of all these novel ADHs the (R)-specific enzymes were found in strains of the genus Lactobacillus. Meanwhile, these new enzymes were characterized extensively. Protein data (amino acid sequence, bound cations) confirm that these catalysts are novel enzymes. (R)-specific as well as (S)-specific ADHs accept a broad variety of ketones and ketoesters as substrates. The applicability of alcohol dehydrogenases for chiral syntheses as an example for the technical use of coenzyme-dependent enzymes is demonstrated and discussed in this contribution. In particular NAD-dependent enzymes coupled with the coenzyme regeneration by formate dehydrogenase proved to be economically feasible for the production of fine chemicals.

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Abbreviations

ADH:

alcohol dehydrogenase

YADH:

yeast alcohol dehydrogenase

HLADH:

horse liver alcohol dehydrogenase

TBADH:

Thermoanaerobium brockii alcohol dehydrogenase

FDH:

formate dehydrogenase

References

  1. Enzyme Nomenclature (1979) New York: Academic Press

    Google Scholar 

  2. Hummel W, Kula M-R (1989) Eur J Biochem 184: 1

    CAS  Google Scholar 

  3. Kula M-R, Wandrey C (1987) Meth Enzymol 136:9

    CAS  Google Scholar 

  4. Kragl U, Vasic-Racki D, Wandrey C (1993) Indian J Chem 32B: 103

    CAS  Google Scholar 

  5. Kim MJ, Whitesides GM (1988) J Am Chem Soc 110: 2959

    CAS  Google Scholar 

  6. Hogan JK, Parris W, Gold M, Jones JB (1992) Bioorg Chem 20: 204

    CAS  Google Scholar 

  7. Hummel W, Schütte H, Kula M-R (1983) Europ J Appl Microbiol Biotechnol 18: 75

    CAS  Google Scholar 

  8. Simon ES, Plante R, Whitesides GM (1989) Appl Biochem Biotechnol 22: 169

    CAS  Google Scholar 

  9. Bradshaw CW, Wong C-H, Hummel W, Kula M-R (1991) Bioorganic Chemistry 19: 29

    CAS  Google Scholar 

  10. Kim M-J, Kim JY (1991) J Chem Soc, Chem Commun: 326

    Google Scholar 

  11. Hummel W, Schütte H, Kula M-R (1985) Appl Microbiol Biotechnol 21: 7

    CAS  Google Scholar 

  12. Schütte H, Hummel W, Kula M-R (1984) Appl Microbiol Biotechnol 19: 167

    Google Scholar 

  13. Hummel W, Schütte H, Kula M-R (1988) Appl Microbiol Biotechnol 28: 433

    CAS  Google Scholar 

  14. Vasic-Racki D, Jonas M, Wandrey C, Hummel W, Kula M-R (1989) Appl Microbiol Biotechnol 31: 215

    CAS  Google Scholar 

  15. Bommarius AS, Drauz K, Hummel W, Kula M-R, Wandrey C, Biocatalysis 10: 37

    Google Scholar 

  16. Bommarius A, Schwarm M, Stingl K, Kottenhan M, Huthmacher K, Drauz K (1995) Tetrahedron: Asymmetry 6: 2851

    CAS  Google Scholar 

  17. Wandrey C, Bossow B (1986) Biotechnol Bioind 3: 8

    Google Scholar 

  18. Hanson RL, Singh J, Kissik TP, Patel RN, Szarka LJ, Mueller RH (1990) Bioorg Chem 18: 116

    CAS  Google Scholar 

  19. Hummel W, Schütte H, Schmidt E, Wandrey C, Kula M-R (1987) Appl Microbiol Biotechnol 26: 409

    CAS  Google Scholar 

  20. Seebach D (1990) Angew Chem 102: 1363

    CAS  Google Scholar 

  21. Nikolova P, Ward OP (1992) Biotechnol Bioeng 39: 870

    CAS  Google Scholar 

  22. Ward OP, Young CS (1990) Enzyme Microb Technol 12: 482

    CAS  Google Scholar 

  23. Servi S (1990) Synthesis: 1

    Google Scholar 

  24. Csuk R, Glänzer B (1991) Chem Rev 91: 49

    CAS  Google Scholar 

  25. Sih CJ, Chen C-S (1984) Angew Chem Int Ed Engl 23: 570

    Google Scholar 

  26. Buisson D, Azerad R, Sanner C, Larcheveque M (1992) Biocatalysis 5: 249

    CAS  Google Scholar 

  27. Seebach D, Roggo S, Maetzke T, Braunschweiger H, Cercus J, Krieger M (1987) Helv Chi Acta 70: 1605

    CAS  Google Scholar 

  28. Sheih W-R, Gopalan AS, Sih CJ (1985) J Am Chem Soc 107: 2993

    Google Scholar 

  29. Bernardi R, Ghiringhelli D (1987) J Org Chem 52: 5021

    CAS  Google Scholar 

  30. Bernardi R, Cardillo R, Ghiringhelli D, de Pavo V (1987) J Chem Soc Perkin Trans I: 1607

    Google Scholar 

  31. Ushio K, Inouye K, Nakamura K, Oka S, Ohno A (1986) Tetrahedron Lett 27: 2657

    CAS  Google Scholar 

  32. Nakamura K, Inoue K, Ushio K, Oka S, Ohno A (1987) Chem Lett: 679

    Google Scholar 

  33. Nakamura K, Kawai Y, Oka S, Ohno A (1989) Bull Chem Soc Jpn 62: 875

    CAS  Google Scholar 

  34. Ushio K, Ebara K, Yamashita T (1991) Enzyme Microb Technol 13: 834

    CAS  Google Scholar 

  35. Chibata I, Tosa T, Sato T (1974) Appl Microbiol 27: 878

    CAS  Google Scholar 

  36. Nakamura K, Higaki M, Ushio K, Oka S, Ohno A (1985) Tetrahedron Lett: 4213

    Google Scholar 

  37. Prelog V (1964) Pure Appl Chem 9: 119

    CAS  Google Scholar 

  38. Jones JB, Jakovac IJ (1982) Can J Chem 60: 19

    CAS  Google Scholar 

  39. Pereira RS (1995) Appl Biochem Biotechnol 55: 123

    CAS  Google Scholar 

  40. Kroner K-H, Schütte H, Stach W, Kula M-R (1982) J Chem Tech Biotechnol 32: 130

    CAS  Google Scholar 

  41. Cordes A, Kula M-R (1986) J Chromatography 376: 375

    CAS  Google Scholar 

  42. Wong C-H, Whitesides GM. 1994. Enzymes in synthetic organic chemistry. New York: Pergamon, Elsevier Science Inc

    Google Scholar 

  43. Faber K. 1995. Biotransformations in organic chemistry. Berlin, Heidelberg, New York: Springer-Verlag

    Google Scholar 

  44. Davies HG, Green RH, Kelly DR, Roberts SM. 1989. Biotransformations in preparative organic chemistry. London: Academic Press

    Google Scholar 

  45. Morrison JD. 1985. Chiral Catalysis. London: Academic Press

    Google Scholar 

  46. Sheldon JD. 1993. Chirotechnology. New York: Marcel Dekker

    Google Scholar 

  47. Millership JS, Fitzpatrick A (1993) Chirality 5: 573

    CAS  Google Scholar 

  48. Hummel W. (1997) In Frontiers in Biosensorics, ed. F. Scheller, J. Fedrowitz, F. Schubert. Basel: Birkhäuser, p. 47

    Google Scholar 

  49. Goodhue CT. 1982. In Microbial transformations of bioactive compounds, Vol. I, ed. J.P. Rosazza, pp. 9. Boca Raton, Florida: CRC Press

    Google Scholar 

  50. Elander RP. 1987. In Basic Biotechnology, ed. J. Bu'Lock, B. Kristiansen, pp. 217. London: Academic Press

    Google Scholar 

  51. Cheetham PSJ (1987) Enz Microb Technol 9: 194

    CAS  Google Scholar 

  52. Hummel W, Weiss N, Kula M-R (1984) Arch Microbiol 137: 47

    CAS  Google Scholar 

  53. Hummel W, Schmidt E, Wandrey C, Kula M-R (1986) Appl Microbiol Biotechnol 25: 175

    CAS  Google Scholar 

  54. Hummel W, Schmidt E, Schütte H, Kula M-R. 1987. In Proceedings Biochemical Engineering, ed. H.-J. Chmiel, pp. 392 Stuttgart: Fischer Verlag

    Google Scholar 

  55. Hummel W, Wendel U, Sting S. 1992. In Biosensors: Fundamentals, Technologies and Applications., ed. F. Scheller, R.D. Schmid, pp. 381. Weinheim: VCH Publisher

    Google Scholar 

  56. Schneider KH, Jakel G, Hoffmann R, Giffhorn F (1995) Microbiology 141: 1865

    CAS  Google Scholar 

  57. Lamed R, Keinan E. J. G. Z (1981) Enzyme Microb Technol 3: 144

    CAS  Google Scholar 

  58. Guagliardi A, Martino M, Iaccarino I, Derosa M, Rossi M, Bartolucci S (1996) Int J Biochem Cell Biol 28: 239

    CAS  Google Scholar 

  59. Rella R, Raia CA, Pensa M, Pisani FM, Gambacorta A, de Rosa M, Rossi M (1987) Eur J Biochem 167:475

    CAS  Google Scholar 

  60. Ammendola S, Raia CA, Caruso C, Camardella L, Dauria S, Derosa M, Rossi M (1992) Biochemistry 31: 12514

    CAS  Google Scholar 

  61. Bradshaw CW, Fu H, Shen G-J, Wong C-H (1992) J Org Chem 57: 1526

    CAS  Google Scholar 

  62. Bradshaw C, Shen G-J, Wong C-H (1991) Bioorg Chem 19: 398

    CAS  Google Scholar 

  63. Suzuki Y, Oishi K, Nakano H, Nagayama T (1987) Appl Microbiol Biotechnol 26: 546

    CAS  Google Scholar 

  64. Wilks HM, Hart KW, Freeney R, Dunn CR, Muirhead H, Chia WN, Barstow DA, Atkinson T, Clarkee AR, Holbrook JJ (1988) Science 242: 1541

    CAS  Google Scholar 

  65. Luyten MA, Bur D, Wynn H, Parris W, Gold M, Friesen JD, Jones JB (1989) J Am Chem Soc 111: 6800

    CAS  Google Scholar 

  66. Corbier C, Clermont S, Billard CP, Skarzynski T, Branlant C, Wonacott A, Branlant G (1990) Biochemistry 29: 7101

    CAS  Google Scholar 

  67. Seelbach K, Riebel B, Hummel W, Kula M-R, Tishkov VI, Egorov AM, Wandrey C, Kragl U (1996) Tetrahedron Lett 37: 1377

    CAS  Google Scholar 

  68. Tishkov VI, Galkin AG, Kulakova LB, Egorov AM. 1993. In Enzyme Engineering XII. Deauville, France

    Google Scholar 

  69. Tishkov VI, Galkin AG, Marchenko GN, Tsygankov YD, Egorov AM (1993) Biotechnol Appl Biochem 18: 201

    CAS  Google Scholar 

  70. Cronin CN, Malcolm BA, Kirsch JF (1987) J Am Chem Soc 109: 2222

    CAS  Google Scholar 

  71. Murali C, Creaser EH (1986) Protein Engineering 1: 55

    CAS  Google Scholar 

  72. Zhong Z, Liu JL-C, Dinterman LM, Finkelman MAJ, Mueller WT, Rollence ML, Whitlow M, Wong C-H (1991) J Am Chem Soc 113: 683

    CAS  Google Scholar 

  73. Bonneau PR, Graycar TP, Estell DA, Jones JB (1991) J Am Chem Soc 113: 1026

    CAS  Google Scholar 

  74. Pantoliano MW, Whitlow M, Wood JF, Dodd SW, Hardman KD, Rollence ML, Bryan PN (1989) Biochemistry 28: 7205

    CAS  Google Scholar 

  75. Russell AJ, Fersht AR (1987) Nature: 328

    Google Scholar 

  76. Russell AJ, Fersht AR (1987) Nature: 496

    Google Scholar 

  77. Fersht A, Winter G (1992) TIBS: 92

    Google Scholar 

  78. Wells JA, Estell DA (1988) Trends Biochem Sci 13: 291

    CAS  Google Scholar 

  79. Jörnvall H, Persson B, Jeffery J (1987) Eur J Biochem 167: 195

    Google Scholar 

  80. Reid MF, Fewson CA (1994) Crit Rev Microbiol 20: 13

    CAS  Google Scholar 

  81. Persson B, Krook M, Jörnvall H (1991) Eur J Biochem 200: 537

    CAS  Google Scholar 

  82. Persson B, Zigler JS, Jörvall H (1994) Eur J Biochem 226: 15

    CAS  Google Scholar 

  83. Schauder S, Schneider K-H, Giffhorn F (1995) Microbiology 141: 1857

    CAS  Google Scholar 

  84. MacKintosh RW, Fewson CA (1988) Biochem J 250: 743

    CAS  Google Scholar 

  85. Mallinder PR, Pritchard A, Moir A (1992) Gene 110: 9

    CAS  Google Scholar 

  86. Hummel W (1990) Appl Microbiol Biotechnol 34: 15

    CAS  Google Scholar 

  87. Lamed RJ, Zeikus JG (1981) Biochem J 195: 183

    CAS  Google Scholar 

  88. Lamed RJ, Zeikus JG (1980) J Bacteriol 141: 1251

    CAS  Google Scholar 

  89. Conway T, Ingram LO (1989) J Bacteriol 171: 3754

    CAS  Google Scholar 

  90. Riebel B, Hummel W. 1996 pers. commun.

    Google Scholar 

  91. Saliola M, Shuster JR, Falcone C (1990) Yeast 6: 193

    CAS  Google Scholar 

  92. Bränden C-I, Jörnvall H, Eklund H, Furugren B. 1975. In The Enzymes Vol. 11 ed PD Boyer, pp. 103 New York Academic Press

    Google Scholar 

  93. Jörnvall H, von Bahr-Lindström H, Jeffery J (1984) Eur J Biochem 140: 17

    Google Scholar 

  94. Riebel B. 1996. Thesis, University of Düsseldorf, Düsseldorf

    Google Scholar 

  95. Jörnvall H, Persson B, Jeffery J (1987) Eur J Biochem 167: 195

    Google Scholar 

  96. Borrás T, Persson B, Jörnvall H (1987) Eur J Biochem 28: 6133

    Google Scholar 

  97. Aronson BD, Somerville RL, Epperly BR, Dekker EE (1989) J. Biol Chem 264: 5226

    CAS  Google Scholar 

  98. Karlsson C, Maret W, Auld DS, Höög J-O, Jörnvall H (1989) Eur J Biochem 186: 543

    CAS  Google Scholar 

  99. Bright JR, Byrom D, Danson MJ, Hough DW, Towner P (1993) Eur J Biochem 211 549

    CAS  Google Scholar 

  100. Amy CM, Witkowski A, Naggert J, Williams B, Randhawa Z, Smith S (1989) Proc Natl Acad Sci USA 86: 3114

    CAS  Google Scholar 

  101. Donadio S, Staver MJ, McAlpine JB, Swanson SJ, Katz L (1991) Science 252: 675

    CAS  Google Scholar 

  102. Eklund H, Nordström B, Zeppezauer E, Söderlund G, Ohlsson I, Boiwe T, Brändén C-I (1974) FEBS Lett 44: 200

    CAS  Google Scholar 

  103. Eklund H, Nordström B, Zeppezauer E, Söderlund G, Ohlsson I, Boiwe T, Söderberg B-O, Tapla O, Bränden C-I (1976) J Mol Biol 102: 27

    CAS  Google Scholar 

  104. Eklund H, Samama J-P, Wallen L, Brändén C-I (1981) J Mol Biol 146: 561

    CAS  Google Scholar 

  105. Cedergen-Zeppezauer ES, Andersson I, Ottonello S (1985) Biochemistry 24: 4000

    Google Scholar 

  106. Jörnvall H, Eklund H, Branden CI (1978) J Biol Chem 253: 8414

    Google Scholar 

  107. Ganzhorn AJ, Green DW, Hershey AD, Gould RM, Plapp BV (1987) J Biol Chem 262: 3754

    CAS  Google Scholar 

  108. Jörnvall H, von Bahr-Lindström H, Jany K-D, Ulmer W, Fröschle M (1984) FEBS Lett 165: 190

    Google Scholar 

  109. Jörnvall H, Persson M, Jeffery J (1981) Proc Natl Acad Sci USA 78: 4226

    Google Scholar 

  110. Thatcher DR, Sawyer L (1980) Biochem J 187: 884

    CAS  Google Scholar 

  111. Villarroya A, Juan E, Egestad B, Jörnvall H (1989) Eur J Biochem J 180: 191

    CAS  Google Scholar 

  112. Dothie JM, Giglio JR, Moore CB, Taylor SS, Hartley BS (1985) Biochem J 230: 569

    CAS  Google Scholar 

  113. Taylor SS, Rigby PJW, Hartley BS (1974) Biochem J 141: 693

    CAS  Google Scholar 

  114. Pauly HE, Pfleiderer G (1975) Hoppe-Seylers Z Physiol Chem. 356: 1613

    CAS  Google Scholar 

  115. Jany KD, Ulmer W, Froschle M, Pfleiderer G (1984) FEBS Lett 165: 6

    CAS  Google Scholar 

  116. Conway T, Sewell GW, Osman YA, Ingram IO (1987) J Bacteriol 169: 2591

    CAS  Google Scholar 

  117. Williamson VM, Paquin CE (1987) Mol Gen Genet 209: 374

    CAS  Google Scholar 

  118. Chou PY, Fasman GD (1974) Biochemistry 13: 222

    CAS  Google Scholar 

  119. You KS (1984) Crit Rev Biotechnol 17: 313

    Google Scholar 

  120. Arnold LJ, You K, Allison WS, Kaplan NO (1976) Biochemistry 15: 4844

    CAS  Google Scholar 

  121. Dodds DR, Jones JB (1988) J Am Chem Soc 110: 577

    CAS  Google Scholar 

  122. Nakazaki M, Chikamatsu H, Naemura K, Hirose Y, Shimizu T, Asao M (1978) J Chem Soc Chem Commun: 667

    Google Scholar 

  123. Nakazaki M, Chikamatsu H, Naemura K, Asao M (1980) J Org Chem 45: 4432

    CAS  Google Scholar 

  124. Nakazaki M, Chikamatsu H, Naemura K, Suzuki T, Iwasaki M, Sasaki Y, Fujii T (1981) J Org Chem 46: 2726

    CAS  Google Scholar 

  125. Nakazaki M, Chikamatsu H, Fujii T, Susaki Y, Ao S (1983) J Org Chem 48: 4337

    CAS  Google Scholar 

  126. Hansch C, Bjorkroth (1986) J Org Chem 51: 5461

    CAS  Google Scholar 

  127. Dutler H, Branden C-I (1981) Bioorg Chem 10: 1

    CAS  Google Scholar 

  128. Horjales E, Branden C-I (1985) J Biol Chem 260: 15445

    CAS  Google Scholar 

  129. Lemière GL, van Osselaer TA, Lepovire JA, Alderweireldt FC (1982) J Chem Soc Perkin Trans II: 1123

    Google Scholar 

  130. Kuassman J, Petterson G (1980) Eur J Biochem 103: 557

    Google Scholar 

  131. Klinman JP (1981) Crit Rev Biochem: 39

    Google Scholar 

  132. MacLeod R, Prosser H, Fikentscher L, Lanyi J, Mosher HS (1964) Biochemistry 3: 838

    CAS  Google Scholar 

  133. Nakamura K, Miyai T, Kawai J, Nakajima N, Ohno A (1990) Tetrahedron Lett: 1159

    Google Scholar 

  134. Wong C-H, Whitesides GM (1983) J Am Chem Soc 105: 5012

    CAS  Google Scholar 

  135. Mansson MO, Larsson PO, Mosbach K (1982) Meth Enzymol 89: 457

    Google Scholar 

  136. Wang SS, King C-K (1979) Adv Biochem Eng 12: 119

    CAS  Google Scholar 

  137. Dodds DR, Jones JB (1982) J Chem Soc, Chem Commun: 1080

    Google Scholar 

  138. Keinan E, Hafeli EK, Seth KK, Lamed R (1986) J Am Chem Soc 108: 162

    CAS  Google Scholar 

  139. Keinan E, Seth KK, Lamed R, Ghirlando R, Singh SP (1990) Biocatalysis 3: 57

    CAS  Google Scholar 

  140. Keinan E, Sinha SC, Shinha-Bagchi A (1991) J Chem Soc, Perkin Trans 1: 3333

    Google Scholar 

  141. Lee LG, Whitesides GM (1986) J Org Chem 51: 25

    CAS  Google Scholar 

  142. Carrea G, Bovara R, Longhi R, Riva S (1985) Enzyme Microb Technol 7: 597

    CAS  Google Scholar 

  143. Carrea G (1984) Trends Biotechnol 2: 102

    CAS  Google Scholar 

  144. Carrea G, Bovara R, Longhi R, Barani R (1984) Enzyme Microbiol Technol 6: 307

    CAS  Google Scholar 

  145. Hummel W, Boermann F, Kula M-R (1989) Biocatalysis 2: 293

    CAS  Google Scholar 

  146. Hata H, Sihimizu S, Hattori S, Yamada H (1990) J Org Chem 55: 4377

    CAS  Google Scholar 

  147. Peters J, Zelinski T, Minuth T, Kula M-R (1993) Tetrahedron Asymmetry 4: 1173

    CAS  Google Scholar 

  148. Peters J, Minuth T, Kula M-R (1993) Enzyme Microb Technol 15: 950

    CAS  Google Scholar 

  149. Shimizu S, Hattori S, Hata H, Yamada H (1988) Eur J Biochem 174: 37

    CAS  Google Scholar 

  150. Hata H, Shimizu S, Hattori H, Yamada H (1989) FEMS Microbiol Lett 58: 87

    CAS  Google Scholar 

  151. Hata H, Shimizu S, Hattori H Yamada H (1989) Biochim Biophys Acta 990: 175

    CAS  Google Scholar 

  152. Shimizu S, Hata H, Yamada H (1984) Agric Biol Chem 48: 2285

    CAS  Google Scholar 

  153. Tischer W, Bader J, Simon H (1979): Eur J Biochem 97: 103

    CAS  Google Scholar 

  154. Simon H, Günther H, Bader J, Tischer W (1981) Angew Chem Int Ed Engl 20: 861

    Google Scholar 

  155. Simon H, Bader J, Günther H, Neumann S, Thanos J (1985) Angew Chem Int Ed Engl 24: 539

    Google Scholar 

  156. Keinan E, Seth KK, Lamed R (1987) Ann NY Acad Sci 501: 130

    Google Scholar 

  157. Hummel W (1990) Biotechnol Lett 12: 403

    CAS  Google Scholar 

  158. Humel W, Goffwald, C. (1991) Ger. Pat. Appl. P 42.09.022.9

    Google Scholar 

  159. Kruse W, Hummel W, Kragl U (1996) Recl Trav Chim Pays-Bas 115: 239

    CAS  Google Scholar 

  160. Bradshaw CW, Hummel W, Wong C-H (1992) J Org Chem 57: 1532

    CAS  Google Scholar 

  161. Hughes MN, Poole RK 1989 Metals and micro-organisms London, Chapman and Hall

    Google Scholar 

  162. Westerhausen D, Herrmann S, Hummel W, Steckhan E (1992) Angew Chem Int Ed Engl 31: 1592

    Google Scholar 

  163. 1974. Bergey's Mannual of Determinative Bacteriology. Baltimore: Willians & Wilkins

    Google Scholar 

  164. Orla S. 1919 The lactic acid bacteria Copenhagen: Fred Host and Son

    Google Scholar 

  165. Orla S. 1943 The lactic acid bacteria, Corpenhagen: Munksgaard

    Google Scholar 

  166. Rogosa M (1970) In J System Bact 20: 519

    Google Scholar 

  167. Wilkinson BJ, Jones D (1977) J Gen Microbiol 98: 399

    CAS  Google Scholar 

  168. Williams RAD (1971) J Dent Res 50: 1104

    Google Scholar 

  169. Buyze G, van den Hamer CJA, de Haan PG (1957) J Microbiol Serol 23: 345

    CAS  Google Scholar 

  170. Delong A, Calderonurrea A, Dellaporta SL (1993) Cell 74: 757

    CAS  Google Scholar 

  171. Yoshimoto T, Hagashi H, Kanatani A, Lin XS, Nagai H, Oyama H, Kurazono K, Tsuru D (1991) J Bacteriol 173:2173

    CAS  Google Scholar 

  172. Krook M, Marekov L, Jörnvall H (1990) Biochemistry 29: 738

    CAS  Google Scholar 

  173. Yamamoto-Otake H, Koyama Y, Horiuchi T, Nakano E (1991) Appl Environ Microbiol 57: 1418

    CAS  Google Scholar 

  174. Neidle E, Hartnett C, Ornston N, Bairoch A, Rekik M, Harayama S (1992) Eur J Biochem 204: 113

    CAS  Google Scholar 

  175. Hofer B, Eltis LD, Dowling DN, Timmis KN (1993) Gene 130: 47

    CAS  Google Scholar 

  176. Verwoert IIGS, Verbree EC, van der Linden KH, Nijkamp HJJ, Stuitje AR (1992) J Bacteriol 174: 2851

    CAS  Google Scholar 

  177. Yin SJ, Vagelopoulos N, Lundquist G, Jörnvall H (1991) Eur J Biochem 197: 359

    CAS  Google Scholar 

  178. Marekov L, Krook M, Jörnvall H (1990) FEBS Lett 266: 51

    CAS  Google Scholar 

  179. Tannin GM, Agarwal AK, Monder C, New MI, White PC (1991) J Biol Chem 266: 16653

    CAS  Google Scholar 

  180. Agarwal AK, Monder C, Eckstein B, White PC (1989) J Biol Chem 264: 18939

    CAS  Google Scholar 

  181. Albalat R, Gonzàlez-Duarte R, Atrian S (1992) FEBS Lett 308: 235

    CAS  Google Scholar 

  182. Ensor CM, Tai H-H (1991) Biochem Biophys Res Commun 176: 840

    CAS  Google Scholar 

  183. Chen Z, Jiang JC, Lin ZG, Lee WR, Baker ME, Chang SH (1993) Biochemistry 32: 3342

    CAS  Google Scholar 

  184. Krook M, Prozorovski V, Atrian S, Gonzàlez-Duarte R, Jörnvall H (1992) Eur J Biochem 209: 233

    CAS  Google Scholar 

  185. Murdock GL, Chin CC, Warren JC (1986) Biochemistry 25: 641

    CAS  Google Scholar 

  186. Wong C-H, Whitesides GM (1981) J Am Chem Soc 103: 4890

    CAS  Google Scholar 

  187. Johnson SL, Tuazon PT (1977) Biochemistry 16: 1175

    CAS  Google Scholar 

  188. Oppenheimer NJ, Kaplan NO (1974) Biochemistry 13: 4675

    CAS  Google Scholar 

  189. Janssen DB, Keuning S, Witholt B (1987) J Gen Micorbiol 133: 85

    CAS  Google Scholar 

  190. Rigby DJ, Dodgson KS, White GF (1986) J Gen Microbiol 132: 35

    CAS  Google Scholar 

  191. Steinbüchel A, Schlegel HG (1984) Eur J Biochem 141: 555

    Google Scholar 

  192. Bellion E, Wu GT-S (1978) J Bacteriol 135: 251

    CAS  Google Scholar 

  193. Yamanaka K, Minoshima R (1984) Agric Biol Chem 48: 171

    Google Scholar 

  194. Hou CT, Patel R, Laskin AI, Barnabe N, Marczak I (1979) Appl Environ Microbiol 38: 135

    CAS  Google Scholar 

  195. Hou CT, Patel R, Barnabe N, Marczak I (1981) Eur J Biochem 199: 359

    Google Scholar 

  196. Hiu SF, Zhu C-X, Yan R-T, Chen J-S (1987) Appl Environ Microbiol 53: 697

    CAS  Google Scholar 

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

    CAS  Google Scholar 

  198. Jones JB, Sneddon DW, Higgins W, Lewis AJ (1972) J Chem Soc Chem Commun: 856

    Google Scholar 

  199. Vandecasteele J-P, Lemal J (1980) Bull Soc Chim France 101

    Google Scholar 

  200. Wienkamp R, Steckhan E (1983) Angew Chem Int Ed Engl 22: 497

    Google Scholar 

  201. Mandler D, Willner I (1984) J Am Chem Soc 106: 5352

    CAS  Google Scholar 

  202. Mandler D, Willner I (1986) J Chem Soc, Perk Trans 2: 805

    Google Scholar 

  203. Bader J, Günther H, Nagata S, Schütz H-J, Link M-L, Simon H (1984) J Biotechnol 1: 95

    CAS  Google Scholar 

  204. Günther H, Frank C, Schütz H-J, Bader J, Simon H (1983) Angew Chem Int Ed Engl 22: 322

    Google Scholar 

  205. Day RJ, Kinsey SJ, Seo ET, Weliky N, Silverman HP (1972) Trans NY Acad Sci 34: 588

    CAS  Google Scholar 

  206. Steckhan E, Hermann S, Ruppert R, Dietz E, Frede M, Spika E (1991) Organometallics 10: 1568

    CAS  Google Scholar 

  207. Ruppert R, Herrmann S, Steckhan E (1987) Tetrahedron Lett 28: 6583

    CAS  Google Scholar 

  208. Ruppert R, Herrmann S, Stekhan E (1988) J Chem Soc Chem Commun: 1150

    Google Scholar 

  209. Steckhan E, Herrmann S, Ruppert R, Thömmes J, Wandrey C (1990) Angew Chem Int Ed Engl 29: 388

    Google Scholar 

  210. Wichmann R, Wandrey C, Bückmann AF, Kula M-R (1981) Biotechnol Bioeng 23: 2789

    CAS  Google Scholar 

  211. Shaked Z, Whitesides GM (1980) J Am Chem Soc. 102: 7104

    CAS  Google Scholar 

  212. Schen G-J, Wang Y-F, Wong C-H (1990) J Chem Soc, Chem Commun 9: 677

    Google Scholar 

  213. Wong C-H, Drueckhammer DG, Sweers HW (1985) J Am Chem Soc 107: 4028

    CAS  Google Scholar 

  214. Egorov AM, Avilova TV, Dikov MM, Popov VO, Radionov YV, Berezin IV (1979) Eur J Biochem 99: 569

    CAS  Google Scholar 

  215. Wong C-H, Matos JR (1985) J Org Chem 50: 1992

    CAS  Google Scholar 

  216. Wong C-H, McCurry SD, Whitesides GM (1980) J Am Chem Soc 102: 7938

    CAS  Google Scholar 

  217. Lee LG, Whitesides GM (1985) J Am Chem Soc 107: 6999

    CAS  Google Scholar 

  218. Carrea G, Bovara R, Cremonesi P, Lodi R (1984) Biotechnol Bioeng 26: 560

    CAS  Google Scholar 

  219. Wong C-H, Whitesides GM (1982) J Org Chem 47: 2816

    CAS  Google Scholar 

  220. Lemière GL, Lepoivre JA, Alderweireldt FC (1985) Tetrahedr Lett 26: 4527

    Google Scholar 

  221. Chambers RP, Walle EM, Baricos WH, Cohen W (1978) Enz Eng 3: 363

    Google Scholar 

  222. Jones JB, Taylor KE (1973) Chem Comm: 205

    Google Scholar 

  223. Jones JB, Taylor KE (1976) Can J Chem 54: 2974

    CAS  Google Scholar 

  224. Jones JB, Taylor KE (1976) Can J Chem 54 2969

    CAS  Google Scholar 

  225. Hummel W, Riebel B (1996) Enz Eng 13: 713

    Google Scholar 

  226. Cambou B, Klibanov AM (1984) J Am Chem Soc 106: 2687

    CAS  Google Scholar 

  227. Yokozeki K, Yamanaka S, Takinami K, Hirose Y, Tanaka A, Sonomoto K, Fukui S. (1982) Eur J Appl Microbiol Biotechnol 14: 1

    CAS  Google Scholar 

  228. Martinek K, Semenov AN, Berezin IV (1981) Biocheim Biophys Acta 658: 76

    CAS  Google Scholar 

  229. Klibanov AM, Samokhin GP, Martinek K, Berezin IV (1977) Biotechnol Bioeng 19: 1351

    CAS  Google Scholar 

  230. Dastol FR, Musto NA, Price S (1966) Arch Biochem Biophys 115: 44

    Google Scholar 

  231. Laane C, Boeren S, Hilhorst RC, Veeger C. 1987. In Biocatalysis in Organic Media, ed. C. Laane, J. Tramper, M.D. Lilly, pp. 65. Amsterdam

    Google Scholar 

  232. Laane C, Boeren S, Vos K, Voeger C (1987) Biotechnol Bioeng 30: 81

    CAS  Google Scholar 

  233. Zaks A., Klibanov AM (1988) J Biol Chem 263: 8017

    CAS  Google Scholar 

  234. Zaks A, Klibanov AM (1988) J Biol Chem 263: 3194

    CAS  Google Scholar 

  235. Schinkel JE, Downer NW, Rupley JA (1985) Biochemistry 24: 352

    CAS  Google Scholar 

  236. Liusi PL, Laane C (1986) TIBTECH: 153

    Google Scholar 

  237. Careri G, Gratton E, Yang P-H, Rupley JA (1980) Nature 284: 572

    CAS  Google Scholar 

  238. Kragl U, Kruse W, Hummel W, Wandrey C (1996) Biotechnol Bioeng (in press)

    Google Scholar 

  239. Zagalak B, Frey PA, Karabatsos GL, Abeles RH (1966) J Biol Chem 241: 3028

    CAS  Google Scholar 

  240. Krawczyk AR, Jones JB (1989) J Org Chem 54: 1795

    CAS  Google Scholar 

  241. Nakazaki M, Chikamatsu H, Taniguchi M (1982) Chem Lett: 1761

    Google Scholar 

  242. Jones JB, Takemura T (1984) Can J Chem 62: 77

    CAS  Google Scholar 

  243. Davies J, Jones JB (1979) J Am Chem Soc 101: 5405

    CAS  Google Scholar 

  244. Haslegrave JA, Jones JB (1982) J Am Chem Soc 104: 4666

    CAS  Google Scholar 

  245. Sadozai SK, Lepoivre JA, Dommisse RA, Alderweireldt FC (1980) Bull Soc Chim Belg 89: 637

    CAS  Google Scholar 

  246. Jones JB, Schwartz HM (1981) Can J Chem 59: 1574

    CAS  Google Scholar 

  247. Jones JB. 1985. In Enzymes in organic synthesis, pp. 3. London: Pitman

    Google Scholar 

  248. Drueckhammer DG, Sadozai SK, Wong C-H, Roberts SM (1987) Enzyme Microb Technol 9: 564

    CAS  Google Scholar 

  249. Naemura K, Katoh T, Chikamatsu H, Nakasaki M (1984) Chem Lett: 1371

    Google Scholar 

  250. Bridges AJ, Raman PS, Ng GSY, Jones JB (1984) J Am Chem Soc 106: 1461

    CAS  Google Scholar 

  251. Jakovac JJ, Goodbrand HB, Lok KP, Jones JB (1982) J Am Chem Soc 104: 4559

    Google Scholar 

  252. Yamazaki Y, Hosono K (1988) Tetrahedron Lett 29: 5769

    CAS  Google Scholar 

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  1. Institut für Enzymtechnologie, der Heinrich-Heine-Universität, Forschungszentrum Jülich, Postfach 2050, D-52404, Jülich, Germany

    Werner Hummel

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Dedicated to Professor Dr. Maria-Regina Kula on the occasion of her 60th birthday

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Hummel, W. (1997). New alcohol dehydrogenases for the synthesis of chiral compounds. In: New Enzymes for Organic Synthesis. Advances in Biochemical Engineering/Biotechnology, vol 58. Springer, Berlin, Heidelberg. https://doi.org/10.1007/BFb0103304

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