A three-dimensional predictive active site model for lipase from Pseudomonas cepacia

被引：65

作者：

Lemke, K ^{[1
]}

Lemke, M ^{[1
]}

Theil, F ^{[1
]}

机构：

[1] BERLIN ADLERSHOF EV,INST ANGEW CHEM,D-12484 BERLIN,GERMANY

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1997年 / 62卷 / 18期

关键词：

D O I：

10.1021/jo970838d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A three-dimensional active site model of lipase from Pseudomonas cepacia-one of the most popular lipases in organic synthesis-was developed on the basis of the kinetic revolution of 3-(aryloxy)propan-2-ols. Size and shape of both hydrophobic binding pockets of the active site of this lipase were determined by substrate mapping in combination with molecular modeling for substrates and nonsubstrates. This model explains and predicts whether a compound is accepted as a substrate or not and allows to assess the enantiomer selectivity of the lipase-catalyzed reaction.

引用

页码：6268 / 6273

页数：6

共 67 条

[1] LIPASE-CATALYZED STEREOSELECTIVE THIOTRANSESTERIFICATION OF MERCAPTO ESTERS [J].

BIANCHI, D ;

CESTI, P .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (21) :5657-5659

[2] ENZYMATIC RESOLUTION OF 1,2-DIOLS - PREPARATION OF OPTICALLY PURE DROPROPIZINE [J].

BIANCHI, D ;

BOSETTI, A ;

CESTI, P ;

GOLINI, P .

TETRAHEDRON LETTERS, 1992, 33 (22) :3231-3234

[3] AMINE ASSISTED ENZYMATIC ESTERIFICATION OF 1,2-DIOL MONOTOSYLATES [J].

BOAZ, NW ;

ZIMMERMAN, RL .

TETRAHEDRON-ASYMMETRY, 1994, 5 (02) :153-156

[4]

BOLAND W, 1991, SYNTHESIS-STUTTGART, P1049

[5] RESOLUTION OF (+/-)-TRANS-SOBREROL BY LIPASE PS-CATALYZED TRANSESTERIFICATION AND EFFECTS OF ORGANIC-SOLVENTS ON ENANTIOSELECTIVITY [J].

BOVARA, R ;

CARREA, G ;

FERRARA, L ;

RIVA, S .

TETRAHEDRON-ASYMMETRY, 1991, 2 (09) :931-938

[6] WATER ACTIVITY DOES NOT INFLUENCE THE ENANTIOSELECTIVITY OF LIPASE PS AND LIPOPROTEIN-LIPASE IN ORGANIC-SOLVENTS [J].

BOVARA, R ;

CARREA, G ;

OTTOLINA, G ;

RIVA, S .

BIOTECHNOLOGY LETTERS, 1993, 15 (02) :169-174

[7] A SERINE PROTEASE TRIAD FORMS THE CATALYTIC CENTER OF A TRIACYLGLYCEROL LIPASE [J].

BRADY, L ;

BRZOZOWSKI, AM ;

DEREWENDA, ZS ;

DODSON, E ;

DODSON, G ;

TOLLEY, S ;

TURKENBURG, JP ;

CHRISTIANSEN, L ;

HUGEJENSEN, B ;

NORSKOV, L ;

THIM, L ;

MENGE, U .

NATURE, 1990, 343 (6260) :767-770

[8] ENZYMATIC RESOLUTION OF 2-HYDROXY-4-PHENYLBUTANOIC ACID AND 2-HYDROXY-4-PHENYLBUTENOIC ACID [J].

CHADHA, A ;

MANOHAR, M .

TETRAHEDRON-ASYMMETRY, 1995, 6 (03) :651-652

[9] GENERAL-ASPECTS AND OPTIMIZATION OF ENANTIOSELECTIVE BIOCATALYSIS IN ORGANIC-SOLVENTS - THE USE OF LIPASES [J].

CHEN, CS ;

SIH, CJ .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1989, 28 (06) :695-707

[10] QUANTITATIVE-ANALYSES OF BIOCHEMICAL KINETIC RESOLUTIONS OF ENANTIOMERS [J].

CHEN, CS ;

FUJIMOTO, Y ;

GIRDAUKAS, G ;

SIH, CJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (25) :7294-7299

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