Klebsiella pneumoniae (NBRC 3319) Mediated Asymmetric Reduction of α-Substituted β-Oxo Esters and Its Application to the Enantioiselective Synthesis of Small-Ring Carbocycle Derivatives

被引：12
作者：
Bhuniya, Rajib [1 ]
Mahapatra, Tridib [1 ]
Nanda, Samik [1 ]
机构：
[1] Indian Inst Technol, Dept Chem, Kharagpur 721302, W Bengal, India
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 2012卷 / 08期
关键词：
Ketoreductases; Biotransformations; Small ring systems; Asymmetric synthesis; DYNAMIC KINETIC RESOLUTION; ETHYL; 2-METHYL-3-OXOBUTANOATE; STEREOSELECTIVE REDUCTION; BIOCATALYTIC REDUCTION; TRANSFER HYDROGENATION; SECONDARY ALCOHOLS; SEC-ALCOHOLS; ENZYME; OXIDATION; KETONES;
D O I：
10.1002/ejoc.201101695
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Ketoreductases from Klebsiella pneumoniae (NBRC 3319) selectively reduce several 2-substituted ethyl 3-oxobutyrates to yield the corresponding syn-beta-hydroxy esters with remarkable stereocontrol (de > 99 %, ee > 99 %). The enantiopure hydroxy oxo esters were synthetically manipulated to access new small-ring carbocycles.
引用
收藏
页码：1597 / 1602
页数：6
相关论文
共 51 条
[1]   Synthesis of L- and D-4,6-Dideoxyhexoses and 4,6-Dideoxy-C-phenylglycosides from Enzyme-Generated Products [J].
Acetti, Daniela ;
Brenna, Elisabetta ;
Fuganti, Claudio ;
Gatti, Francesco G. ;
Malpezzi, Luciana ;
Serra, Stefano .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (30) :5125-5134
[2]   Selective oxidation of secondary alcohols [J].
Arterburn, JB .
TETRAHEDRON, 2001, 57 (49) :9765-9788
[3]   Dynamic resolution and stereoinversion of secondary alcohols by chemo-enzymatic processes [J].
Azerad, R ;
Buisson, D .
CURRENT OPINION IN BIOTECHNOLOGY, 2000, 11 (06) :565-571
[4]   New Trends in the Recycling of NAD(P)H for the Design of Sustainable Asymmetric Reductions Catalyzed by Dehydrogenases [J].
Berenguer-Murcia, Angel ;
Fernandez-Lafuente, Roberto .
CURRENT ORGANIC CHEMISTRY, 2010, 14 (10) :1000-1021
[5]  
Bornscheuer UT, 2006, HYDROLASES IN ORGANIC SYNTHESIS: REGIO- AND STEREOSELECTIVE BIOTRANSFORMATIONS, 2ND EDITION, P1
[6]  
Carnell A J, 1999, Adv Biochem Eng Biotechnol, V63, P57
[7]   Recent advances in the synthetic applications of the oxazaborolidine-mediated asymmetric reduction [J].
Cho, Byung Tae .
TETRAHEDRON, 2006, 62 (33) :7621-7643
[8]   Recent development and improvement for boron hydride-based catalytic asymmetric reduction of unsymmetrical ketones [J].
Cho, Byung Tae .
CHEMICAL SOCIETY REVIEWS, 2009, 38 (02) :443-452
[9]   Vegetables as chemical reagents [J].
Cordell, Geoffrey A. ;
Lemos, Telma L. G. ;
Monte, Francisco J. Q. ;
de Mattos, Marcos C. .
JOURNAL OF NATURAL PRODUCTS, 2007, 70 (03) :478-492
[10]  
Drauz K., 2002, ENZYME CATALYSIS ORG, VIII, P991
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