One-pot chemoenzymatic synthesis of protected cyanohydrins

Tetrahedron

Volumn 60, Issue 3, 2004, Pages 735-739

  Purkarthofer, Thomas ^a   Skranc, Wolfgang ^b   Weber, Hansjörg ^a   Griengl, Herfried ^a   Wubbolts, Marcel ^b   Scholz, Gerald ^b   Pöchlauer, Peter ^b  

^a GRAZ UNIVERSITY OF TECHNOLOGY   (Austria)

^b DSM Fine Chemicals Austria Nfg GmbH & Co KG   (Netherlands)

Author keywords

Chemoenzymatic synthesis; Cyanohydrins; Ethyl cyanoformate; Hydroxynitrile lyase (PaHNL)

Indexed keywords

BENZALDEHYDE; CYANOHYDRIN; ETHYL CYANOFORMATE; FORMIC ACID DERIVATIVE; HYDROXYNITRILE LYASE; ORGANIC COMPOUND; UNCLASSIFIED DRUG; WATER;

ADDITION REACTION; ARTICLE; CARBONYLATION; CATALYSIS; CATALYST; ENANTIOSELECTIVITY; ENZYME SYNTHESIS; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; PRUNUS;

PRUNUS DULCIS;

EID: 0348225177     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.10.108     Document Type: Article

References (29)

1. (a) Gotor V. Org. Proc. Res. Dev. 6:2002;420-426
2. (b) Gotor V. J. Biotechnol. 96:2002;35-42
3. (c) Effenberger F., Förster S., Wajant H. Curr. Opin. Biotechnol. 11:2000;532-539
4. (d) Johnson D.V., Zabelinskaja-Mackova A.A., Griengl H. Curr. Opin. Chem. Biol. 4:2000;103-109.
5. (a) Fechter M.H., Griengl H. Drauz K., Waldmann H. Enzyme Catalysis in Organic Synthesis. 2002;974-989 Wiley-VCH, Weinheim
6. (b) Griengl H., Schwab H., Fechter M. TIBTECH. 18:2000;252-256
7. (c) Griengl H., Hickel A., Johnson D.V., Kratky C., Schmidt M., Schwab H. Chem. Commun. 1997;1933-1940
8. (d) Effenberger F. Angew. Chem. 106:1994;1609-1619.
9. For reviews see: (a) Gregory R.J.H. Chem. Rev. 99:1999;3649-3682 (b) North M. Tetrahedron: Asymmetry. 14:2003;147-176.
10. For reviews see: (a) Gregory R.J.H. Chem. Rev. 99:1999;3649-3682 (b) North M. Tetrahedron: Asymmetry. 14:2003;147-176.
11. Hanefeld U., Straathof A.J.J., Heijnen. J. Mol. Catal. B Enzym. 11:2001;213-218.
12. (a) Inagaki M., Hiratake J., Nishioka T., Oda. J. Am. Chem. Soc. 113:1991;9360-9361
13. (b) Inagaki M., Hiratake J., Nishioka T., Oda. J. Org. Chem. 57:1992;5643-5649
14. (c) Inagaki M., Hatanaka A., Mimura M., Hiratake J., Nishioka T., Oda. J. Bull. Chem. Soc. Jpn. 65:1992;111-120.
15. (a) Kanerva L.T., Rahiala K., Sundholm O. Biocatalysis. 10:1994;169-180
16. (b) Paizs C., Tosa M., Majdik C., Tähtinen P., Irimie F.D., Kanerva L.T. Tetrahedron: Asymmetry. 14:2003;619-627.
17. see also (c) Li Y.-X., Straathof A.J.J., Hanefeld U. Tetrahedron: Asymmetry. 13:2002;739-743.
18. For reviews see: (a) El Gihani M.T., Williams J.M.J. Curr. Opin. Chem. Biol. 3:1999;11-15 (b) Huerta F.F., Minidis A.B.E., Bäckvall J.-E. Chem. Soc. Rev. 30:2001;321-331.
19. For reviews see: (a) El Gihani M.T., Williams J.M.J. Curr. Opin. Chem. Biol. 3:1999;11-15 (b) Huerta F.F., Minidis A.B.E., Bäckvall J.-E. Chem. Soc. Rev. 30:2001;321-331.
20. (a) Tian S.-K., Deng L.J. Am. Chem. Soc. 123:2001;6195-6196
21. (b) Tian J., Yamagiwa N., Matsunaga S., Shibasaki M. Angew. Chem. 114:2002;3788-3790
22. (c) Casas J., Baeza A., Sansano J.M., Nájera C., Saá J.M. Tetrahedron: Asymmetry. 14:2003;197-200.
23. Schwab, H.; Glieder, A.; Kratky, C.; Dreveny, I.; Poechlauer, P.; Skranc, W.; Mayrhofer, H.; Wirth, I.; Neuhofer, R.; Bona, R. EP 1223220 (DSM Fine Chemicals, Austria).
24. Weber H., Brecker L. Curr. Opin. Biotechnol. 11:2000;572-578.
25. (a) Wehtje E., Adlercreutz P., Mattiasson B. Biotechnol. Bioeng. 36:1990;39-46
26. (b) Wehtje E., Adlercreutz P., Mattiasson B. Biotechnol. Bioeng. 41:1993;171-178
27. (c) Costes D., Wehtje E., Adlercreutz P. Enzyme Microb. Technol. 25:1999;384-391
28. (d) Persson M., Costes D., Wehtje E., Adlercreutz P. Enzyme Microb. Technol. 30:2002;916-923.
29. Kimura M., Kuboki A., Sugai T. Tetrahedron: Asymmetry. 13:2002;1059-1068.