Hydroxynitrile lyase catalysed synthesis of heterocyclic (R)- and (S)-cyanohydrins

被引:25
作者
Avi, M
Fechter, MH
Gruber, K
Bela, F
Pöchlauer, P
Griengl, H
机构
[1] Graz Univ Technol, Inst Organ Chem, A-8010 Graz, Austria
[2] Res Ctr Appl Biocatalysis, Graz, Austria
[3] Karl Franzens Univ Graz, Inst Chem, A-8010 Graz, Austria
[4] DSM Fine Chem Austria, A-4021 Linz, Austria
关键词
hydroxynitrile lyase; cyanohydrins; heterocyclic ketones; enzyme-catalysed;
D O I
10.1016/j.tet.2004.07.099
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Heterocyclic saturated five- and six-membered ring ketones sometimes bearing a methyl substituent were reacted with HCN under enzyme catalysis using recombinant hydroxynitrile lyase from Hevea brasiliensis, as a rule (S)-selective, and Prunus amygdalus, (R)selective. The resulting cyanohydrins were stereochemically characterised. The steric outcome of these transformations was interpreted by molecular modelling. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:10411 / 10418
页数:8
相关论文
共 34 条
[1]   REINDARSTELLUNG UND EIGENSCHAFTEN DER OXYNITRILASE AUS BITTEREN MANDELN [J].
BECKER, W ;
ESCHENHOF, E ;
BENTHIN, U ;
PFEIL, E .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1963, 75 (01) :93-+
[2]   On the selectivity of oxynitrilases towards α-oxygenated aldehydes [J].
Bianchi, P ;
Roda, G ;
Riva, S ;
Danieli, B ;
Zabelinskaja-Mackova, A ;
Griengl, H .
TETRAHEDRON, 2001, 57 (11) :2213-2220
[3]   HYDROBORATION .71. HYDROBORATION OF REPRESENTATIVE HETEROCYCLIC OLEFINS WITH BORANE-METHYL SULFIDE, 9-BORABICYCLO[3.3.1]NONANE, DICYCLOHEXYLBORANE, AND DISIAMYLBORANE - SYNTHESIS OF HETEROCYCLIC ALCOHOLS [J].
BROWN, HC ;
PRASAD, JVNV ;
ZEE, SH .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (10) :1582-1589
[4]  
BRUSSEE J, 2000, STEREOSELECTIVE BIOC, P289
[5]  
CASE DA, 1997, AMBER V6 0
[6]   Hydroxynitrile lyase-catalyzed addition of HCN to 4-substituted cyclohexanones:: stereoselective preparation of tetronic acids [J].
Effenberger, F ;
Roos, J ;
Kobler, C ;
Bühler, H .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 2002, 80 (06) :671-679
[7]  
Effenberger F, 2002, ANGEW CHEM INT EDIT, V41, P1876, DOI 10.1002/1521-3773(20020603)41:11<1876::AID-ANIE1876>3.0.CO
[8]  
2-1
[9]  
EFFENBERGER F, 2000, STEREOSELECTIVE BIOC, P321
[10]   Oxidation of olefins by palladium(II) Part 17. An asymmetric chlorohydrin synthesis catalyzed by a bimetallic palladium(II) complex [J].
El-Qisairi, A ;
Henry, PM .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2000, 603 (01) :50-60