Cleavage and Formation of Cyanohydrins

Enzyme Catalysis in Organic Synthesis, Third Edition

Volumn 2, Issue , 2012, Pages 947-990

  Gruber Khadjawi, Mandana ^a   Fechter, Martin H ^b   Griengl, Herfried ^a  

^a GRAZ UNIVERSITY OF TECHNOLOGY   (Austria)

^b Austrian Foundry Research Institute   (Austria)

Author keywords

Biotransformations; Cyanohydrin Cleavage; Cyanohydrin formation; Enzyme promiscuity; Hydroxynitrile lyases; Resolution of racemates

Indexed keywords

EID: 84886595474     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527639861.ch23     Document Type: Chapter

References (323)

1. Gregory, R.J.H. (1999) Chem. Rev., 99, 3649-3682.
2. North, M. (2003) Tetrahedron: Asymmetry, 14, 147-176.
3. Chen, F.-X. and Feng, X. (2006) Curr. Org. Synth., 3, 77-97.
4. Brussee, J. and van der Gen, A. (2000) Biocatalysis in the enantioselective formation of chiral cyanohydrins, valuable building blocks in organic synthesis, in Stereoselective Biocatalysis (ed. R.N. Patel),Marcel Dekker Inc., New York/Basel, pp. 289-320.
5. Effenberger, F. (2000) Hydroxynitrile lyases in stereoselective synthesis, in Stereoselective Biocatalysis (ed. R.N. Patel) Marcel Dekker Inc., New York/Basel, pp. 321-342.
6. van der Gen, A. and Brussee, J. (2000) Stereoselective biocatalytic formation of cyanohydrins, versatile building blocks for organic synthesis, in Enzymes in Action (eds B. Zwanenburg, M. Mikolajczyk, and P. Kielbasinski), Kluwer Academic Publishers, The Netherlands, pp. 365-396.
7. Holt, J. and Hanefeld, U. (2009) Curr. Org. Synth., 6, 15-37.
8. Brunel, J.-M. and Holmes, I.P. (2004) Angew. Chem., Int. Ed., 43, 2752-2778.
9. Achard, T.R.J., Clutterbuck, L.A., and North, M. (2005) Synlett, 12, 1828-1847.
10. Khan, N.H., Kureshy, R.I., Abdi, S.H.R., Agrawal, S., and Jasra, R.V. (2008) Coord. Chem. Rev., 252, 593-623.
11. North, M., Usanov, D.L., and Young, C. (2008) Chem. Rev., 108, 5146-5226. 12 Jones, P.R., Andersen, M.D., Nielsen, J.S., Høj, P.B., and Møller, B.L. (2000) Recent Adv. Phytochem., 34, 191-247.
12. Dewick, P.M. (1984) Nat. Prod. Rep., 1, 545-549.
13. Poulton, J.E. (1990) Plant Physiol., 94, 401-405.
14. Rosenthaler, L. (1908) Biochem. Z., 14, 238-253.
15. Krieble, V.K. and Wieland, W.A. (1921) J. Am. Chem. Soc., 43, 164-175.
16. Albers, H. and Hamann, K. (1932) Biochem. Z., 255, 44-65.
17. Albers, H. and Hamann, K. (1934) Biochem. Z., 269, 14-25.
18. Becker, W., Benthin, U., Eschenhof, E., and Pfeil, E. (1963) Biochem. Z., 337, 156-166.
19. Becker, W. and Pfeil, E. (1964) Naturwissenschaften, 51, 193.
20. Becker, W., Freund, H., and Pfeil, E. (1965) Angew. Chem., Int. Ed. Engl., 4, 1079.
21. Becker, W. and Pfeil, E. (1966) Biochem. Z., 346, 301-321.
22. Becker, W. and Pfeil, E. (1966) J. Am. Chem. Soc., 88, 4299-4300.
23. Akazawa, T., Miljanich, P., and Conn, E.E. (1960) Plant Physiol., 35, 535-538.
24. Bové, C. and Conn, E.E. (1961) J. Biol. Chem., 236, 207-210.
25. Seely, M.K., Criddle, R.S., and Conn, E.E. (1966) J. Biol. Chem., 241, 4457-4462.
26. Mao, C.-H. and Anderson, L. (1967) Phytochemistry, 6, 473-483.
27. Conn, E.E. (1981) Cyanogenic glycosides, in The Biochemistry of Plants: a Comprehensive Treatise, vol. 7 (eds P.K. Stumpf and E.E. Conn), Academic Press, New York, pp. 479-500.
28. Seigler, D.S. (1991) Cyanide and cyanogenic glycosides, in Hervivores: Their Interactions with Secondary Plant Metabolites: Volume 1 The Chemical Participants, 2nd edn, (eds G.A. Rosenthal and M.R. Berenbaum), Academic Press, New York, pp. 35-77.
29. Lechtenberg, M. and Nahrstedt, A. (1999) Cyanogenic glycosides, in Naturally Occurring Glycosides, (ed. R. Ikan), John Wiley & Sons, Ltd., Chichester, pp. 147-191.
30. Effenberger, F., Foerster, S., and Kobler, C. (2007) State of the art and applications in stereoselective synthesis of chiral cyanohydrins, in Biocatalysis in the Pharmaceutical and Biotechnology Industries (ed. R. Patel), CRC Press, Boca Raton, pp. 677-698.
31. Sharma, M., Sharma, N.N., and Bhalla, T.C. (2005) Enzyme Microb. Technol., 37, 279-294.
32. Fechter, M.H. and Griengl, H. (2004) Food Technol. Biotechnol., 42, 287-294.
33. Effenberger, F., Forster, S., and Wajant, H. (2000) Curr. Opin. Biotechnol., 11, 532-539.
34. Johnson, D.V., Zabelinskaja-Mackova, A.A., and Griengl, H. (2000) Curr. Opin. Chem. Biol., 4, 103-109.
35. Seoane, G. (2000) Curr. Org. Chem., 4, 283-304.
36. Johnson, D.V. andGriengl, H. (1999) Adv. Biochem. Eng./Biotechnol., 63, 31-55.
37. Sukumaran, J. and Hanefeld, U. (2005) Chem. Soc. Rev., 34, 530-542.
38. Liu, Z., Weis, R., and Glieder, A. (2004) Food Technol. Biotechnol., 42, 237-249.
39. Mugford, P.F., Wagner, U.G., Jiang, Y., Faber, K., and Kazlauskas, R.J. (2008) Angew. Chem., Int. Ed., 47, 8782-8793.
40. Hickel, A., Hasslacher, M., and Griengl, H. (1996) Physiol. Plant., 98, 891-898.
41. Jorns, M.S. (1979) J. Biol. Chem., 254, 12145-12152.
42. Wajant, H. and Effenberger, F. (1996) Biol. Chem., 377, 611-617.
43. Hasslacher, M., Kratky, C., Griengl, H., Schwab, H., and Kohlwein, S.D. (1997) Proteins: Struct., Funct., Genet., 27, 438-449.
44. Gruber, K. and Kratky, C. (2004) J. Polym. Sci. Pol. Chem., 42, 479-486.
45. Effenberger, F. (1994) Angew. Chem., Int. Ed. Engl., 33, 1555-1564.
46. Effenberger, F., Horsch, B.,Weingart, F., Ziegler, T., and Kuhner, S. (1991) Tetrahedron Lett., 32, 2605-2608.
47. Effenberger, F., Hörsch, B.,Weingart, F., Ziegler, T., and Kühner, S. (1991) Tetrahedron Lett., 32, 2605-2608.
48. Nanda, S., Kato, Y., and Asano, Y. (2005) Tetrahedron, 61, 10908-10916.
49. Gregory, R.J.H., Roberts, S.M., Barkley, J.V., Coles, S.J., Hursthouse, M.B., and Hibbs, D.E. (1999) Tetrahedron Lett., 40, 7407-7411.
50. Kiljunen, E. and Kanerva, L.T. (1997) Tetrahedron: Asymmetry, 8, 1225-1234.
51. Kiljunen, E. and Kanerva, L.T. (1997) Tetrahedron: Asymmetry, 8, 1551-1557.
52. Bhunya, R., Jana, N., Das, T., and Nanda, S. (2009) Synlett, 1237-1240.
53. Bhunja, R., Mahapatra, T., and Nanda, S. (2009) Tetrahedron: Asymmetry, 20, 1526-1530.
54. Lin, G., Han, S., and Li, Z. (1999) Tetrahedron, 55, 3531-3540.
55. de Gonzalo, G., Brieva, R., and Gotor, V. (2002) J. Mol. Catal. B: Enzym., 19-20, 223-230.
56. Weis, R., Poechlauer, P., Bona, R., Skranc, W., Luiten, R., Wubbolts, M.G., Schwab, H., and Glieder, A. (2004) J. Mol. Catal. B: Enzym., 29, 211-218.
57. Glieder, A., Weis, R., Skranc, W., Poechlauer, P., Dreveny, I., Majer, S., Wubbolts, M., Schwab, H., and Gruber, K. (2003) Angew. Chem., Int. Ed., 42, 4815-4818.
58. Dreveny, I., Gruber, K., Glieder, A., Thompson, A., and Kratky, C. (2001) Structure (Cambridge), 9, 803-815.
59. Pscheidt, B., Avi, M., Gaisberger, R., Hartner, F.S., Skranc,W., and Glieder, A. (2008) J. Mol. Catal. B: Enzym., 52-53, 183-188.
60. Hernández, L., Luna, H., Ruiz-Teran, F., and Vazquez, A. (2004) J. Mol. Catal. B: Enzym., 30, 105-108.
61. Hernández, L., Luna, H., Solís, A., and Vázquez, A. (2006) Tetrahedron: Asymmetry, 17, 2813-2816.
62. Solís, A., Luna, H., Manjarrez, N., and Pérez, H. (2004) Tetrahedron, 60, 10427-10431.
63. Solís, A., Luna, H., Pérez, H.I., Manjarrez, N., and Sánchez, R. (1998) Rev. Soc. Quim. Mex., 42, 214-216.
64. Solís, A., Luna, H., Pérez, H.I., Manjarrez, N., Sánchez, R., Albores- Velasco, M., and Castillo, R. (1998) Biotechnol. Lett., 20, 1183-1185.
65. Solís, A., Luna, H., Pérez, H.I., Manjarrez, N., and Sánchez, R. (2002) Rev. Mex. Cienc. Farm., 33, 27-31.
66. Lee, T. and Ahn, Y. (2002) Bull. Korean Chem. Soc., 23, 1490-1492.
67. Poechlauer, P., Skranc, W., and Wubbolts, M. (2004) The large-scale biocatalytic synthesis of enantiopure cyanohydrins, in Asymmetric Catalysis on Industrial Scale: Challenges, Approaches and Solutions (eds H.U. Blaser and E. Schmidt), Wiley-VCH Verlag GmbH, Weinheim, pp. 151-164.
68. Purkarthofer, T., Skranc,W., Schuster, C., and Griengl, H. (2007) Appl. Microbiol. Biotechnol., 76, 309-320.
69. Rosenthaler, L. (1913) Arch. Pharm., 251, 56-84.
70. Xu, L.L., Singh, B.K., and Conn, E.E. (1988) Arch. Biochem. Biophys., 263, 256-263.
71. Cutler, A.J., Sternberg, M., and Conn, E.E. (1985) Arch. Biochem. Biophys., 238, 272-279.
72. Albrecht, J., Jansen, I., and Kula, M.R. (1993) Biotechnol. Appl. Biochem., 17, 191-203.
73. Roberge, C., Fleitz, F., Pollard, D., and Devine, P. (2007) Tetrahedron: Asymmetry, 18, 208-214.
74. Trummler, K., Roos, J., Schwaneberg, U., Effenberger, F., Förster, S., Pfizenmaier, K., and Wajant, H. (1998) Plant Sci., 139, 19-27.
75. Breithaupt, H., Pohl, M., Bönigk, W., Heim, P., Schimz, K.-L., and Kula, M.-R. (1999) J. Mol. Catal. B: Enzym., 6, 315-332.
76. Wajant, H., Förster, S., Selmar, D., Effenberger, F., and Pfizenmaier, K. (1995) Plant Physiol., 109, 1231-1238.
77. Han, S.-Q., Ouyang, P.-K., Wei, P., and Hu, Y. (2006) Biotechnol. Lett., 28, 1909-1912.
78. Andexer, J., von Langermann, J.,Mell, A., Bocola, M., Kragl, U., Eggert, T., and Pohl, M. (2007) Angew. Chem., Int. Ed., 46, 8679-8681.
79. Guterl, J.-K., Andexer, J.N., Sehl, T., von Langermann, J., Frindi-Wosch, I., Rosenkranz, T., Fitter, J., Gruber, K., Kragl, U., Eggert, T., and Pohl, M. (2009) J. Biotechnol., 141, 166-173.
80. Effenberger, F., Hörsch, B., Förster, S., andZiegler,T. (1990)Tetrahedron Lett., 31, 1249-1252.
81. Niedermeyer, U. and Kula, M.R. (1990) Angew. Chem., Int. Ed. Engl., 29, 386-387.
82. Hasslacher, M., Schall, M., Hayn, M., Griengl, H., Kohlwein, S.D., and Schwab, H. (1996) J. Biol. Chem., 271, 5884-5891.
83. Griengl, H., Hickel, A., Johnson, D.V., Kratky, C., Schmidt, M., and Schwab, H. (1997) Chem. Commun., 1933-1940.
84. Hasslacher, H., Schall, M., Hayn, M., Bona, R., Rumbold, K., Luckl, J., Griengl, H., Kohlwein, S.D., and Schwab, H. (1997) Protein Expression Purif., 11, 61-71.
85. Schmidt, M.,Hervé, S., Klempier, N., and Griengl, H. (1996) Tetrahedron, 52, 7833-7840.
86. Klempier, N., Griengl, H., and Hayn, M. (1993) Tetrahedron Lett., 34, 4769-4772.
87. Danieli, B., Frattini, S., Roda, G., Carrea, G., and Riva, S. (1998) J. Mol. Catal. B: Enzym., 5, 223-228.
88. Roda, G., Riva, S., and Danieli, B. (1999) Tetrahedron: Asymmetry, 10, 3939-3949.
89. Roda, G., Riva, S., Danieli, B., Griengl, H., Rinner, U., Schmidt, M., and Zabelinskaja-Mackova, A.A. (2002) Tetrahedron, 58, 2979-2983.
90. Avi, M., Fechter, M.H., Gruber, K., Belaj, F., Pöchlauer, P., and Griengl, H. (2004) Tetrahedron, 60, 10411-10418.
91. Fröhlich, R.F.G., Zabelinskaja-Mackova, A.A., Fechter, M.H., and Griengl, H. (2003) Tetrahedron: Asymmetry, 14, 355-362.
92. Wagner, U.G., Hasslacher, M., Griengl, H., Schwab, H., and Kratky, C. (1996) Structure (London), 4, 811-822.
93. Wagner, U.G., Schall, M.,Hasslacher, M., Hayn, M., Griengl, H., Schwab, H., and Kratky, C. (1996) Acta Crystallogr., Sect. D, 52, 591-593.
94. Zuegg, J., Gruber, K., Gugganig, M., Wagner, U.G., and Kratky, C. (1999) Protein Sci., 8, 1990-2000.
95. Gruber, K., Gugganig, M.,Wagner, U.G., and Kratky, C. (1999) Biol. Chem., 380, 993-1000.
96. Gruber, K. (2001) Protein Struct., Funct., Genet., 44, 26-31.
97. Avi, M., Wiedner, R.M., Griengl, H., and Schwab, H. (2008) Chem.-Eur. J., 14, 11415-11422.
98. Veum, L., Hanefeld, U., and Pierre, A. (2004) Tetrahedron, 60, 10419-10425.
99. Sheldon, R.A., Schoevaart, R., and L.M van. Langen, (2006) Cross-linked enzyme aggregates, in Methods in Biotechnology, Immobilization of Enzymes and Cells, 2nd edn (ed. J.M. Guisan) Humana Press, Totowa, NJ, pp. 31-45.
100. Gaisberger, R.P., Fechter, M.H., and Griengl, H. (2004) Tetrahedron: Asymmetry, 15, 2959-2963.
101. Purkarthofer, T., Papst, T., van, C., Broek, d., Griengl, H., Maurer, O., and Skranc, W. (2006) Org. Process Res. Dev., 10, 618-621.
102. Lauble, H., Miehlich, B., Förster, S., Wajant, H., and Effenberger, F. (2001) Protein Sci., 10, 1015-1022.
103. Lauble, H., Förster, S., Miehlich, B., Wajant, H., and Effenberger, F. (2001) Acta Cryst., Sect. D, 57, 194-200.
104. Daußmann, T., Rosen, T.C., and Dünkelmann, P. (2006) Eng. Life Sci., 6, 125-129.
105. Förster, S., Roos, J., Effenberger, F., Wajant, H., and Sprauer, A. (1996) Angew. Chem., Int. Ed. Engl., 35, 437-439.
106. Hughes, J., Carvalho, F.J.P.D.C., and Hughes, M.A. (1994) Arch. Biochem. Biophys., 311, 496-502.
107. Hughes, J., Lakey, J.H., and Hughes, M.A. (1997) Biotechnol. Bioeng., 53, 332-338.
108. Effenberger, F., Roos, J., Kobler, C., and Bühler, H. (2002) Can. J. Chem., 80, 671-679.
109. Roos, J. and Effenberger, F. (1999) Tetrahedron: Asymmetry, 10, 2817-2828.
110. Effenberger, F., Roos, J., and Kobler, C. (2002) Angew. Chem., Int. Ed., 41, 1876-1879.
111. Kobler, C., Bohrer, A., and Effenberger, F. (2004) Tetrahedron, 60, 10397-10410.
112. Schmidt, M. and Griengl, H. (1999) Top. Curr. Chem., 200, 193-226.
113. Asano, Y., Tamura, K., Doi, N., Ueatrongchit, T., H-Kittikun, A., and Ohmiya, T. (2005) Biosci., Biotechnol., Biochem., 69, 2349-2357.
114. Nanda, S., Kato, Y., and Asano, Y. (2005) Tetrahedron, 61, 10908-10916.
115. Nanda, S., Kato, Y., and Asano, Y. (2006) Tetrahedron: Asymmetry, 17, 735-741.
116. Ueatrongchit, T., Kayo, A., Komeda, H., Asano, Y., and H-Kittikun, A. (2008) Biosci. Biotechnol. Biochem., 72, 1513-1522.
117. Ueatrongchit, T., Komeda, H., Asano, Y., and H-Kittikun, A. (2009) J. Mol. Catal. B: Enzym., 56, 208-214.
118. Huang, S.-R., Liu, S.-L., Zong, M.-H., and Xu, R. (2005) Biotechnol. Lett., 27, 79-82.
119. Solís, A., Luna, H., Pérez, H.I., and Manjarrez, N. (2003) Tetrahedron: Asymmetry, 14, 2351-2353.
120. Brussee, J., Roos, E.C., and van der Gen, A. (1988) Tetrahedron Lett., 29, 4485-4488.
121. Brussee, J., Loos, W.T., Kruse, C.G., and van der Gen, A. (1990) Tetrahedron, 46, 979-986.
122. van Langen, L.M., van Rantwijk, F., and Sheldon, R.A. (2003) Org. Process Res. Dev., 7, 828-831.
123. Effenberger, F., Ziegler, T., and Förster, S. (1987) Angew. Chem., Int. Ed. Engl., 26, 458-460.
124. Wehtje, E., Adlercreutz, P., and Mattiasson, B. (1990) Biotechnol. Bioeng., 36, 39-46.
125. Wehtje, E., Adlercreutz, P., and Mattiasson, B. (1993) Biotechnol. Bioeng., 41, 171-178.
126. Zandbergen, P., van der Linden, J., Brussee, J., and van der Gen, A. (1991) Synth. Commun., 21, 1387-1391.
127. Huuhtanen, T.T. and Kanerva, L.T. (1992) Tetrahedron: Asymmetry, 3, 1223-1226.
128. Menendez, E., Brieva, R., Rebolledo, F., and Gotor, V. (1995) J. Chem. Soc., Chem. Commun., 989-990.
129. Kiljunen, E. and Kanerva, L.T. (1996) Tetrahedron: Asymmetry, 7, 1105-1116.
130. Hulsbos, E., Marcus, J., Brussee, J., and van der Gen, A. (1997) Tetrahedron: Asymmetry, 8, 1061-1067.
131. Han, S., Lin, G., and Li, Z. (1998) Tetrahedron: Asymmetry, 9, 1835-1838.
132. Chen, P.,Han, S., Lin, G.,Huang, H., and Li, Z. (2002) J. Org. Chem., 67, 8251-8253.
133. Han, S., Chen, P., Lin, G.,Huang, H., and Li, Z. (2001) Tetrahedron: Asymmetry, 12, 843-846.
134. Chen, P.,Han, S., Lin, G.,Huang, H., and Li, Z. (2001) Tetrahedron: Asymmetry, 12, 3273-3279.
135. Purkarthofer, T., Gruber, K., Fechter, M., and Griengl, H. (2005) Tetrahedron, 61, 7661-7668.
136. Ognyanov, V.I., Datcheva, V.K., and Kyler, K.S. (1991) J. Am. Chem. Soc., 113, 6992-6996.
137. Monterde, M.I., Nazabadioko, S., Rebolledo, F., Brieva, R., and Gotor, V. (1999) Tetrahedron: Asymmetry, 10, 3449-3455.
138. Monterde, M.I., Brieva, R., and Gotor, V. (2001) Tetrahedron: Asymmetry, 12, 525-528.
139. Kragl, U., Niedermeyer, U., Kula, M.-R., and Wandrey, C. (1990) Ann. N. Y. Acad. Sci., 613, 167-175.
140. Loos, W.T., Geluk, H.W., Ruijken, M.M.A., Kruse, C.G., Brussee, J., and van derGen, A. (1995) Biocatal. Biotransform., 12, 255-266.
141. Gröger, H., Capan, E., Barthuber, A., and Vorlop, K.-D. (2001) Org. Lett., 3, 1969-1972.
142. Trummler, K. and Wajant, H. (1997) J. Biol. Chem., 272, 4770-4774.
143. Brussee, J., Dofferhoff, F., Kruse, C.G., and van der Gen, A. (1990) Tetrahedron, 46, 1653-1658.
144. Kiljunen, E. and Kanerva, L.T. (1997) Tetrahedron: Asymmetry, 8, 1551-1557.
145. Wajant, H. and Pfizenmaier, K. (1996) J. Biol. Chem., 271, 25830-25834.
146. Butler, G.W. (1965) Phytochemistry, 4, 127-131.
147. Lieberei, R. (1988) J. Phytopathol., 122, 54-67.
148. Selmar, D., Lieberei, R., Biehl, B., and Conn, E.E. (1989) Physiol. Plant., 75, 97-101.
149. Klempier, N., Pichler, U., and Griengl, H. (1995) Tetrahedron: Asymmetry, 6, 845-848.
150. Elliott, M., Farnham, A.W., Janes, N.F., Needham, P.H., and Pulman, D.A. (1974) ACS Symp. Ser., 2, 80-91.
151. Briggs, G.G., Elliott, M., Farnham, A.W., and Janes, N.F. (1974) Pestic. Sci., 5, 643-649.
152. Elliott, M., Farnham, A.W., Janes, N.F., Needham, P.H., and Pulman, D.A. (1974) Nature, 248, 710-711.
153. Moss, G.P. (1999) IUBMB Enzyme Nomenclature, EC 4.1.2.39, International Union of Biochemistry and Molecular Biology, http://www.chem.qmw.ac.uk/iubmb/enzyme/EC4/1/2/39.html. (accessed in 1999)
154. Wajant, H., Förster, S., Böttinger, H., Effenberger, F., and Pfizenmaier, K. (1995) Plant Sci. (Shannon, Irel.), 108, 1-11.
155. Effenberger, F. and Heid, S. (1995) Tetrahedron: Asymmetry, 6, 2945-2952.
156. Effenberger, F. and Gaupp, S. (1999) Tetrahedron: Asymmetry, 10, 1765-1775.
157. Li, N., Zong, M.-H., Liu, C., Peng, H.-S., and Wu, H.C. (2003) Biotechnol. Lett., 25, 219-222.
158. Effenberger, F., Roos, J., and Kobler, C. (2002) Angew. Chem., Int. Ed., 41, 1876-1879.
159. Griengl, H., Klempier, N., Pöchlauer, P., Schmidt, M., Shi, N., and Zabelinskaja- Mackova, A.A. (1998) Tetrahedron, 54, 14477-14486.
160. Buhler, H., Bayer, A., and Effenberger, F. (2000) Chem.-Eur. J., 6, 2564-2571.
161. Li, N., Zong, M.-H., Peng, H.-S.,Wu, H.- C., and Liu, C. (2003) J. Mol. Catal. B: Enzym., 22, 7-12.
162. Xu, R., Zong, M.-H., Liu, Y.-Y., He, J., Zhang, Y.-Y., and Lou, W.-Y. (2004) Appl. Microbiol. Biotechnol., 66, 27-33.
163. Liu, S.L., Zong, M.H., and Huang, S.R. (2005) Chin. Chem. Lett., 16, 1317-1320.
164. Purkarthofer, T., Skranc, W., Weber, H., Griengl, H., Wubbolts, M., Scholz, G., and Pöchlaner, P. (2004) Tetrahedron, 60, 735-739.
165. Rotcenkovs, G. and Kanerva, L.T. (2000) J. Mol. Catal. B: Enzym., 11, 37-43.
166. Hanefeld, U., Straathof, A.J.J., and Heijnen, J.J. (2001) J. Mol. Catal. B: Enzym., 11, 213-218.
167. Bornemann, S. (2002) Nat. Prod. Rep., 19, 761-772.
168. Dreveny, I., Gruber, K., Glieder, A., Thompson, A., and Kratky, C. (2001) Structure (Cambridge, MA), 9, 803-815.
169. Dreveny, I., Kratky, C., and Gruber, K. (2002) Protein Sci., 11, 292-300.
170. Dreveny, I., Andryushkova, A., Glieder, A., Gruber, K., and Kratky, C. (2009) Biochemistry, 48, 3370-3377.
171. Jorns, M.S. (1980) Biochim. Biophys. Acta, 613, 203-209.
172. Cascão-Pereira, L.G., Hickel, A., Radke, C.J., and Blanch, H.W. (2003) Biotechnol. Bioeng., 78, 595-605.
173. Cascão-Pereira, L.G., Hickel, A., Radke, C.J., and Blanch, H.W. (2003) Biotechnol. Bioeng., 83, 498-501.
174. Hickel, A., Radke, C.J., and Blanch, H.W. (1999) Biotechnol. Bioeng., 65, 425-436.
175. Hickel, A., Radke, C.J., and Blanch, H.W. (2001) Biotechnol. Bioeng., 74, 18-28.
176. Hickel, A., Radke, C.J., and Blanch, H.W. (1998) J. Mol. Catal. B: Enzym., 5, 349-354.
177. Gerrits, P.J., Willeman, W.F., Straathof, A.J.J., Heijnen, J.J., Brussee, J., and van der Gen, A. (2001) J. Mol. Catal. B: Enzym., 15, 111-121.
178. Hanefeld, U., Stranzl, G., Straathof, A.J.J., Heijnen, J.J., Bergmann, A., Mittelbach, R., Glatter, O., and Kratky, C. (2001) Biochim. Biophys. Acta, 1544, 133-142.
179. Gartler, G., Kratky, C., and Gruber, K. (2007) J. Biotechnol., 129, 87-97.
180. Gruber, K., Gartler, G., Krammer, B., Schwab, H., and Kratky, C. (2004) J. Biol. Chem., 279, 20501-20510.
181. Stranzl, G.R.,Gruber, K., Steinkellner, G., Zangger, K., Schwab, H., and Kratky, C. (2004) J. Biol. Chem., 279, 3699-3707.
182. Schmidt, A., Gruber, K., Kratky, C., and Lamzin, V.S. (2008) J. Biol. Chem., 283, 21827-21836.
183. Bauer, M., Griengl, H., and Steiner, W. (1999) Biotechnol. Bioeng., 62, 20-29.
184. Bauer, M., Geyer, R., Griengl, H., and Steiner, W. (2002) Food Technol. Biotechnol., 40, 9-19.
185. Purkarthofer, T., Gruber, K., Gruber- Khadjawi, M., Waich, K., Skranc, W., Mink, D., and Griengl, H. (2006) Angew. Chem., Int. Ed., 45, 3454-3456.
186. Gruber-Khadjawi, M., Purkarthofer, T., Skranc, W., and Griengl, H. (2007) Adv. Synth. Catal., 349, 1445-1450.
187. Lauble, H., Miehlich, B., Förster, S., Kobler, C., Wajant, H., and Effenberger, F. (2002) Protein Sci., 11, 65-71.
188. Wajant, H., Boettinger, H., and Mundry, K.W. (1993) Biotechnol. Appl. Biochem., 18, 75-82.
189. Wajant, H. and Mundry, K.W. (1993) Plant Sci., 89, 127-133.
190. Wajant, H., Mundry, K.W., and Pfizenmaier, K. (1994) Plant Mol. Biol., 26, 735-746.
191. Lauble, H., Miehlich, B., Förster, S., Wajant, H., and Effenberger, F. (2002) Biochemistry, 41, 12043-12050.
192. Jaeger, K.-E., Eggert, T., Eipper, A., and Reetz, M.T. (2001) Appl. Microbiol. Biotechnol., 55, 519-530.
193. Berglund, P. and Park, S. (2005) Curr. Org. Chem., 9, 325-336.
194. Fox, R.J. and Huisman, G.W. (2008) Trends Biotechnol., 26, 132-138.
195. Wang, Q. and Withers, S.G. (1995) J. Am. Chem. Soc., 117, 10137-10138.
196. de Raadt, A., Griengl, H., and Weber, H. (2001) Chem.-Eur. J., 7, 27-31.
197. de Raadt, A. and Griengl, H. (2002) Curr. Opin. Biotechnol., 13, 537-542.
198. Li, Z., van Beilen, J.B., Duetz, W.A., Schmid, A., de Raadt, A.,Griengl, H., and Witholt, B. (2002) Curr. Opin. Chem. Biol., 6, 136-144.
199. Fechter, M.H., Gruber, K., Avi, M., Skranc, W., Schuster, C., Pöchlauer, P., Klepp, K.O., and Griengl, H. (2007) Chem.-Eur. J., 13, 3369-3376.
200. Gaisberger, R., Weis, R., Luiten, R., Skranc, W., Wubbolts, M., Griengl, H., and Glieder, A. (2007) J. Biotechnol., 129, 30-38.
201. Liu, Z., Pscheidt, B., Avi, M., Gaisberger, R.,Hartner, F.S., Schuster, C., Skranc,W., Gruber, K., and Glieder, A. (2008) ChemBioChem, 9, 58-61.
202. Buhler, H., Effenberger, F., Förster, S., Roos, J., and Wajant, H. (2003) ChemBioChem, 4, 211-216.
203. Weis, R., Gaisberger, R., Skranc, W., Gruber, K., and Glieder, A. (2005) Angew. Chem., Int. Ed., 44, 4700-4704.
204. Yan, G., Cheng, S., Zhao, G.,Wu, S., Liu, Y., and Sun,W. (2003) Biotechnol. Lett., 25, 1041-1047.
205. Andexer, J., Guterl, J.-K., Pohl, M., and Eggert, T. (2006) Chem. Commun., 4201-4203.
206. Krammer, B., Rumbold, K., Tschemmernegg, M., Pöchlauer, P., and Schwab, H. (2007) J. Biotechnol., 129, 151-161.
207. Reisinger, C., van Assema, F., Schurmann, M., Hussain, Z., Remler, P., and Schwab, H. (2006) J. Mol. Catal. B: Enzym., 39, 149-155.
208. Pscheidt, B., Liu, Z., Gaisberger, R., Avi, M., Skranc, W., Gruber, K., Griengl, H., and Glieder, A. (2008) Adv. Synth. Catal., 350, 1943-1948.
209. Semba, H., Ichige, E., Imanaka, T., Atomi, H., and Aoyagi, H. (2008) Appl. Microbiol. Biotechnol., 79, 563-569.
210. Semba, H., Dobashi, Y., and Matsui, T. (2008) Biosci. Biotechnol. Biochem., 72, 1457-1463.
211. Hanefeld, U., Gardossi, L., and Magner, E. (2009) Chem. Soc. Rev., 38, 453-468.
212. Sheldon, R.A. (2007) Adv. Synth. Catal., 349, 1289-1307.
213. Costes, D.,Wehtje, E., and Aldercreutz, P. (2001) J. Mol. Catal. B: Enzym., 11, 607-612.
214. Veum, L., Hanefeld, U., and Pierre, A. (2004) Tetrahedron, 60, 10419-10425.
215. Mateo, C., Palomo, J.M., van Langen, L.M., van Rantwijk, F., and Sheldon, R.A. (2004) Biotechnol. Bioeng., 86, 273-276.
216. van Langen, L.M., Selassa, R.P., van Rantwijk, F., and Sheldon, R.A. (2005) Org. Lett., 7, 327-329.
217. Cabriol, F.L., Tan, P.L., Tay, B., Cheng, S., Hanefeld, U., and Sheldon, R.A. (2008) Adv. Synth. Catal., 350, 2329-2338.
218. Chmura, A., van der Kraan, G.M., Kielar, F., van Langen, L.M., van Rantwijk, F., and Sheldon, R.A. (2006) Adv. Synth. Catal., 348, 1655-1661.
219. Cabriol, F.L., Hanefeld, U., and Sheldon, R.A. (2006) Adv. Synth. Catal., 348, 1645-1654.
220. Roberge, C., Fleitz, F., Pollard, D., and Devine, P. (2007) Tetrahedron Lett., 48, 1473-1477.
221. Weis, R., Gaisberger, R., Gruber, K., and Glieder, A. (2007) J. Biotechnol., 129, 50-61.
222. Effenberger, F. and Schwammle, A. (1997) Biocatal. Biotransform., 14, 167-179.
223. Inagaki, M.,Hiratake, J., Nishioka, T., and Oda, J. (1989) Bull. Inst. Chem. Res., Kyoto Univ., 67, 132-135.
224. Inagaki, M.,Hiratake, J., Nishioka, T., and Oda, J. (1991) J. Am. Chem. Soc., 113, 9360-9361.
225. Paizs, C., Tahtinen, P., Lundell, K., Poppe, L., Irimie, F.-D., and Kanerva, L.T. (2003) Tetrahedron: Asymmetry, 14, 1895-1904.
226. Sakai, T., Wang, K., and Ema, T. (2008) Tetrahedron, 64, 2178-2183.
227. van Almsick, A., Buddrus, J., Hönicke- Schmidt, P., Laumen, K., and Schneider, M.P. (1989) J. Chem. Soc., Chem. Commun., 1391-1393.
228. Hsu, S.H., Wu, S.S., Wang, Y.F., and Wong, C.H. (1990) Tetrahedron Lett., 31, 6403-6406.
229. Wang, Y.F., Chen, S.T., Liu, K.K.C., and Wong, C.H. (1989) Tetrahedron Lett., 30, 1917-1920.
230. Xu, Q., Geng, X., and Chen, P. (2008) Tetrahedron Lett., 49, 6440-6441.
231. Mitsuda, S., Yamamoto, H., Umemura, T., Hirohara, H., and Nabeshima, S., (1990) Agric. Biol. Chem., 54, 2907-2912.
232. Fishman, A. and Zviely, M. (1998) Tetrahedron: Asymmetry, 9, 107-118.
233. Effenberger, F., Gutterer, B., Ziegler, T., Eckhardt, E., and Aichholz, R. (1991) Liebigs Ann. Chem., 47-54.
234. Holt, J., Arends, I.W.C.E., Minnaard, A.J., and Hanefeld, U. (2007) Adv. Synth. Catal., 349, 1341-1344.
235. Wiggers, M., Holt, J., Kourist, R., Bartsch, S., Arends, I.W.C.E., Minnaard, A.J., Bornscheuer, U.T., and Hanefeld, U. (2009) J. Mol. Catal. B: Enzym., 60, 82-86.
236. Kourist, R., Dominguez deMaria, P., and Bornscheuer, U.T. (2008) ChemBioChem, 9, 491-498.
237. Inagaki, M.,Hiratake, J., Nishioka, T., and Oda, J. (1992) J. Org. Chem., 57, 5643-5649.
238. Inagaki, M., Hatanaka, A., Mimura, M., Hiratake, J., Nishioka, T., and Oda, J. (1992) Bull. Chem. Soc. Jpn., 65, 111-120.
239. Sakai, T., Miki, Y., Tsuboi, M., Takeuchi, H., Ema, T., Uneyama, K., and Utaka, M. (2000) J. Org. Chem., 65, 2740-3274.
240. Sakai, T., Miki, Y., Nakatani, M., Ema, T., Uneyama, K., and Utaka, M. (1998) Tetrahedron Lett., 39, 5233-5236.
241. Sakai, T., Takayama, T., Ohkawa, T., Yoshio, O., Ema, T., and Utaka, M. (1997) Tetrahedron Lett., 38, 1987-1990.
242. Veum, L., Kanerva, L.T., Halling, P.J., Maschmeyer, T., and Hanefeld, U. (2005) Adv. Synth. Catal., 347, 1015-1021.
243. Bianchi, P., Roda, G., Riva, S., Danieli, B., Zabelinskaja-Mackova, A., and Griengl, H. (2001) Tetrahedron, 57, 2213-2220.
244. Kobler, C. and Effenberger, F. (2005) Chem.-Eur. J., 11, 2783-2787.
245. Kobler, C., Bohrer, A., and Effenberger, F. (2004) Tetrahedron, 60, 10397-10410.
246. Kobler, C. and Effenberger, F. (2004) Tetrahedron: Asymmetry, 15, 3731-3742.
247. Buhler, H., Miehlich, B., and Effenberger, F. (2005) ChemBioChem, 6, 711-717.
248. Cruz Silva, M.M., Sae Melo, M.L., Parolin, M., Tessaro, D., Riva, S., and Danieli, B. (2004) Tetrahedron: Asymmetry, 15, 21-27.
249. Schmidt, M. and Griengl, H. (1999) Top. Curr. Chem., 200, 193-226.
250. Effenberger, F.X. (1992) (R)- and (S)- Cyanohydrins - Their enzymatic synthesis and their reactions, in Microbial Reagents in Organic Synthesis (ed. S. Servi), Kluwer, Dordrecht, pp. 25-33.
251. Kruse, C.G., Geluk, H.W., and van Scharrenburg, G.J.M. (1992) Chim. Oggi, 10, 59-63.
252. Breuer, M. and Hauer, B. (2003) Curr. Opin. Biotechnol., 14, 570-576.
253. Johnson, D.V. and Griengl, H. (1997) Chim. Oggi., 15, 9-13.
254. Deardorff, D.R., Taniguchi, C.M., Nelson, A.C., Pace, A.P., Kim, A.J., Pace, A.K., Jones, R.A., Tafti, S.A., Nguyen, C., O'Connor, C., Tang, J., and Chen, J. (2005) Tetrahedron: Asymmetry, 16, 1655-1661.
255. Ziegler, T., Hörsch, B., and Effenberger, F. (1990) Synthesis, 575-478.
256. Osprian, I., Fechter, M.H., and Griengl, H. (2003) J. Mol. Catal. B: Enzym., 24-25, 89-98.
257. Reisinger, C., Osprian, I., Glieder, A., Schoemaker, H.E., Griengl, H., and Schwab, H. (2004) Biotechnol. Lett., 26, 1675-1680.
258. Zandbergen, P., Brussee, J., van der Gen, A., and Kruse, C.G. (1999) Tetrahedron: Asymmetry, 10, 2817-2828.
259. Marcus, J., Vandermeulen, G.W.M., Brussee, J., and van der Gen, A. (1999) Tetrahedron: Asymmetry, 10, 1617-1622.
260. Duffield, J.J. and Regan, A.C. (1996) Tetrahedron: Asymmetry, 7, 663-666.
261. Buhler, H., Bayer, A., and Effenberger, F. (2000) Chem.-Eur. J., 6, 2564-2571.
262. Roos, J. and Effenberger, F. (2002) Tetrahedron: Asymmetry, 13, 1855-1862.
263. Effenberger, F. and Stelzer, U. (1991) Angew. Chem., Int. Ed. Engl., 30, 873-874.
264. Effenberger, F. and Roos, J. (2000) Tetrahedron: Asymmetry, 11, 1085-1095.
265. Warmerdam, E.G.J.C., Brussee, J., Kruse, C.G., and van der Gen, A. (1993) Tetrahedron, 49, 1063-1070.
266. Effenberger, F., Kremser, A., and Stelzer, U. (1996) Tetrahedron: Asymmetry, 7, 607-618.
267. Gaupp, S. and Effenberger, F. (1999) Tetrahedron: Asymmetry, 10, 1777-1786.
268. Nazabadioko, S., Perez, R.J., Brieva, R., and Gotor, V. (1998) Tetrahedron: Asymmetry, 9, 1597-1604.
269. Gotor, V. (2002) Org. Process Res. Dev., 6, 420-426.
270. Gotor, V. (2002) J. Biotechnol., 96, 35-42.
271. Vink, M.K.S., Schortinghuis, C.A., Mackova-Zabelinskaja, A., Fechter, M., Pöchlauer, P., Castelijns, A.M.C.F., van Maarseveen, J.H., Hiemstra, H., Griengl, H., Schoemaker, H.E., and Rutjes, F.P.J.T. (2003) Adv. Synth. Catal., 345, 483-487.
272. Stelzer, U. and Effenberger, F. (1993) Tetrahedron: Asymmetry, 4, 161-164.
273. Tromp, R.A., van der Hoeven, M., Amore, A., Brussee, J., Overhand, M., van der Marel, G.A., and van der Gen, A. (2003) Tetrahedron: Asymmetry, 14, 1645-1652.
274. Tromp, R.A., van der Hoeven, M., Amore, A., Brussee, J., Overhand, M., van der Marel, G.A., and van der Gen, A. (2001) Tetrahedron: Asymmetry, 12, 1109-1112.
275. van der Nieuwendijk, A.M.C.H., Kriek, N.M.A.J., Brussee, J., van Boom, J.H., and van der Gen, A. (2000) Eur. J. Org. Chem., 3683-3691.
276. Ueberbacher, B.J., Griengl, H., and Weber, H. (2008) Tetrahedron: Asymmetry, 19, 838-846.
277. Johnson, D.V., Felfer, U., and Griengl, H. (2000) Tetrahedron, 56, 781-790.
278. Johnson, D.V., Fischer, R., and Griengl, H. (2000) Tetrahedron, 56, 9289-9295.
279. Avi, M., Gaisberger, R., Feichtenhofer, S., and Griengl, H. (2009) Tetrahedron, 65, 5418-5426.
280. Tromp, R.A., Brussee, J., and van derGen, A. (2003) Org. Biomol. Chem., 1, 3592-3599.
281. van Pelt, S., van Rantwijk, F., and Sheldon, R.A. (2009) Adv. Synth. Catal., 351, 397-404.
282. Rustler, S., Motejadded, H., Altenbuchner, J., and Stolz, A. (2008) Appl. Microbiol. Biotechnol., 80, 87-97.
283. Sheldon, R.A., Schoevaart, R., and van Langen, L.M. (2005) Biocatal. Biotransform., 23, 141-147.
284. Sheldon, R.A. (2005) Green Chem., 7, 267-278.
285. Mateo, C., Chmura, A., Rustler, S., van Rantwijk, F., Stolz, A., and Sheldon, R.A. (2006) Tetrahedron: Asymmetry, 17, 320-323.
286. Sheldon, R.A. (2008) Chem. Commun., 3352-3365.
287. van Pelt, S., van Rantwijk, F., and Sheldon, R.A. (2009) Adv. Synth. Catal., 351, 397-404.
288. von Langermann, J., Guterl, J.-K., Pohl, M., Wajant, H., and Kragl, U. (2008) Bioprocess Biosyst. Eng., 31, 155-161.
289. Willemann W.F., Gerrits, P.J., Hanefeld, U., Brussee, J., Straathof, A.J.J., van der Gen, A., and Heijnen, J.J. (2002) Biotechnol. Bioeng., 77, 239-247.
290. von Langermann, J., Mell, A., Paetzold, E., Daußmann, T., and Kragl, U. (2007) Adv. Synth. Catal., 349, 1418-1424.
291. Wajant, H., Förster, S., Sprauer, A., Effenberger, F., and Pfizenmaier, K. (1996) Ann. N.Y. Acad. Sci., 799, 771-776.
292. Effenberger, F., Ziegler, T., and Forster, S. (1987) Angew. Chem., Int. Ed., 26, 458-460.
293. van den Nieuwendijk, A.M.C.H., Warmerdam, E.G.J.C., Brussee, J., and van der Gen, A. (1995) Tetrahedron: Asymmetry, 6, 801-806.
294. Costes, D.,Wehtje, E., and Adlercreutz, P. (1999) Enzyme Microb. Technol., 25, 384-391.
295. Gotor, V. (2000) Molecules, 5, 290-292.
296. Persson, M., Costes, D., Wehtje, E., and Aldercreutz, P. (2002) Enzyme Microb. Technol., 30, 916-923.
297. Pogorevc, M., Stecher, H., and Faber, K. (2002) Biotechnol. Lett., 24, 857-860.
298. Koch, K., van den Berg, R.J.F., Nieuwland, P.J., Wijtmans, R., Wubbolts, M.G., Schoemaker, H.E., Rutjes, F.P.J.T., and van Hest, J.C.M. (2008) Chem. Eng. J. (Amsterdam), 135, 89-92.
299. Koch, K., van den Berg, R.J.F., Nieuwland, P.J., Wijtmans, R., Schoemaker, H.E., van Hest, J.C.M., and Rutjes, F.P.J.T. (2008) Biotechnol. Bioeng., 99, 1028-1033.
300. Chen, P.R., Gu, J.-X., Wie, Z.-L., Han, S.Q., Li, Z.-Y., and Lin, G. (2003) Chin. J. Chem., 21, 983-993.
301. Chen, P.R., Han, S.Q., Lin, G., and Li, Z.-Y. (2002) J. Org. Chem., 67, 8251-8253.
302. Gerrits, P.J., Marcus, J., Birikaki, L., and van der Gen, A. (2001) Tetrahedron: Asymmetry, 12, 971-974.
303. Avi, M. and Griengl, H. (2008) Biocatalysis in biphasic systems: oxynitrilases, in Organic Synthesis with Enzymes in Non-Aqueous Media (eds G. Carrea and S. Riva), Wiley-VCH Verlag GmbH, Weinheim, pp. 211-226.
304. Gaisberger, R.P., Fechter, M.H., and Griengl, H. (2004) Tetrahedron: Asymmetry, 15, 2959-2963.
305. Lou, W.-Y., Xu, R., and Zong, M.-H. (2005) Biotechnol. Lett., 27, 1387-1390.
306. Hickel, A., Gradnig, G., Griengl, H., Schall, M., and Sterk, H. (1996) Spectrochim Acta, Part A, 52, 93-96.
307. National Research Council (1995) Prudent Practices in the Laboratory: Handling and Disposal of Chemicals, National Academic Press, Washington, D.C.
308. Lewis, R.J. (1999) Sax's Dangerous Properties of IndustrialMaterials, 10th edn, John Wiley & Sons, Inc., New York.
309. Somerville, R.L. (1990) Chem. Eng. Prog., 86, 64-68.
310. Baxter, R. (1977) Ind. Finish. (Wheaton, IL), 53, 38-41.
311. Kiljunen, E. and Kanerva, L.T. (1996) Tetrahedron: Asymmetry, 7, 1105-1116.
312. Warmerdam, E.G.J.C., van den Nieuwendijk, A.M.C.H., Kruse, C.G., Brussee, J., and van der Gen, A. (1996) Recl. Trav. Chim. Pays-Bas, 115, 20-24.
313. Tellitu, I., Badia, D., Dominguez, E., and Garcia, F.J. (1994) Tetrahedron: Asymmetry, 5, 1567-1578.
314. Lu, W., Chen, P., and Lin, G. (2008) Tetrahedron, 64, 7822-7827.
315. Effenberger, F. and Eichhorn, J. (1997) Tetrahedron: Asymmetry, 8, 469-476.
316. Syed, J., Forster, S., and Effenberger, F. (1998) Tetrahedron: Asymmetry, 9, 805-815.
317. Effenberger, F. (1994) Angew. Chem., Int. Ed. Engl., 33, 1555-1564.
318. Effenberger, F., Horsch, B.,Weingart, F., Ziegler, T., and Kuhner, S. (1991) Tetrahedron Lett., 32, 2605-2608.
319. Effenberger, F., Gutterer, B., and Syed, J. (1995) Tetrahedron: Asymmetry, 6, 2933-2943.
320. Brussee, J. and van der Gen, A. (1991) Recl. Trav. Chim. Pays-Bas, 110, 25-26.
321. Effenberger, F., Hopf, M., Ziegler, T., and Hudelmayer, J. (1991) Chem. Ber., 124, 1651-1659.
322. Effenberger, F. and Stelzer, U. (1993) Chem. Ber., 126, 779-786.
323. Jackson, W.R., Jacobs, H.A., Jayatilake, G.S., Matthews, B.R., and Watson, K.G. (1990) Aust. J. Chem., 43, 2045-2062.