Enantioselective acylation of α-aminonitriles catalysed by Candida antarctica lipase.: An unexpected turnover-related racemisation

被引：29

作者：

López-Serrano, P ^{[1
]}

Jongejan, JA ^{[1
]}

van Rantwijk, F ^{[1
]}

Sheldon, RA ^{[1
]}

机构：

[1] Delft Univ Technol, Organ Chem & Catalysis Lab, NL-2628 BL Delft, Netherlands

来源：

TETRAHEDRON-ASYMMETRY | 2001年 / 12卷 / 02期

关键词：

D O I：

10.1016/S0957-4166(01)00011-8

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Candida antarctica lipase B (Novozyme 435) catalysed the enantioselective acylation of 2-amino-2-phenylacetonitrile 1 with ethyl phenylacetate affording a near enantiopure product in 47% yield. Acylation of 1 and 2-amino-4-phenylbutyronitrile with ethyl acetate yielded an unexpected partially racemised final product. The racemisation was shown to be turnover related and is ascribed to the increased acidity of the alpha -proton in the formation of the tetrahedral intermediate in the active site of the enzyme. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：219 / 228

页数：10

共 18 条

[1]

BLAH TC, 1992, APPL MICROBIOL BIOT, V37, P184

[2] NEW ASYMMETRIC TRANSFORMATION OF ALPHA-AMINO-ACID ESTERS WITH (+)-TARTARIC ACID [J].

CLARK, JC ;

PHILLIPPS, GH ;

STEER, MR .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (05) :475-481

[3] Candida antarctica lipase B catalysed amidation of pyroglutamic acid derivatives.: A reaction survey [J].

Conde, S ;

López-Serrano, P ;

Martínez, A .

JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 1999, 7 (5-6) :299-306

[4] Lipase-catalyzed synthesis of chiral amides. A systematic study of the variables that control the synthesis [J].

de Castro, MS ;

Gago, JVS .

TETRAHEDRON, 1998, 54 (12) :2877-2892

[5]

FUKUDA Y, 1971, J FERMENT TECHNOL, V49, P1011

[6]

GASTROCK WH, 1987, Patent No. 4683324

[7]

HULT K, COMMUNICATION

[8]

NAKAI K, 1992, B I CHEM RES KYOTO U, V70, P333

[9] Chiral recognition of alcohol enantiomers in acyl transfer reactions catalysed by Candida antarctica lipase B [J].

Orrenius, C ;

Haeffner, F ;

Rotticci, D ;

Ohrner, N ;

Norin, T ;

Hult, K .

BIOCATALYSIS AND BIOTRANSFORMATION, 1998, 16 (01) :1-+

[10]

PEDERSEN S, 1990, Patent No. 9015868

← 1 2 →