Enzymatic resolution of chiral phosphinate esters

被引：30

作者：

Li, YC

Aubert, SD

Maes, EG

Raushel, FM

机构：

[1] Texas A&M Univ, Dept Chem, College Stn, TX 77842 USA

[2] Texas A&M Univ, Dept Biochem & Biophys, College Stn, TX 77842 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2004年 / 126卷 / 29期

关键词：

D O I：

10.1021/ja048457m

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The bacterial phosphotriesterase has been shown to catalyze the stereoselective hydrolysis of phosphinate esters. The wild-type enzyme preferentially hydrolyzes the SP-enantiomers of methyl phenyl p-X-phenylphosphinate esters by 3 orders of magnitude. The mutant enzyme, I106T/F132A/H254G/H257W, exhibits the opposite stereoselectivity and hydrolyzes the RP-enantiomer up to 30 times faster than the corresponding SP-enantiomer. The enantiomerically pure phosphinate esters, prepared from the kinetic resolution of racemic mixtures, can serve as the entry point for the chemoenzymatic preparation of P-chiral phosphines and phosphine oxides. Copyright © 2004 American Chemical Society.

引用

收藏

页码：8888 / 8889

页数：2

相关论文

共 11 条

[1] High resolution X-ray structures of different metal-substituted forms of phosphotriesterase from Pseudomonas diminuta [J].

Benning, MM ;

Shim, H ;

Raushel, FM ;

Holden, HM .

BIOCHEMISTRY, 2001, 40 (09) :2712-2722

[2] Structural determinants of the substrate and stereochemical specificity of phosphotriesterase [J].

Chen-Goodspeed, M ;

Sogorb, MA ;

Wu, FY ;

Hong, SB ;

Raushel, FM .

BIOCHEMISTRY, 2001, 40 (05) :1325-1331

[3] Enhancement, relaxation, and reversal of the stereoselectivity for phosphotriesterase by rational evolution of active site residues [J].

Chen-Goodspeed, M ;

Sogorb, MA ;

Wu, FY ;

Raushel, FM .

BIOCHEMISTRY, 2001, 40 (05) :1332-1339

[4] Enzymatic synthesis of chiral organophosphothioates from prochiral precursors [J].

Li, WS ;

Li, YC ;

Hill, CM ;

Lum, KT ;

Raushel, FM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (14) :3498-3499

[5] Stereoselective detoxification of chiral sarin and soman analogues by phosphotriesterase [J].

Li, WS ;

Lum, KT ;

Chen-Goodspeed, M ;

Sogorb, MA ;

Raushel, FM .

BIOORGANIC & MEDICINAL CHEMISTRY, 2001, 9 (08) :2083-2091

[6] Operational control of stereoselectivity during the enzymatic hydrolysis of racemic organophosphorus compounds [J].

Li, YC ;

Aubert, SD ;

Raushel, FM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (25) :7526-7527

[7]

MCEWEN WE, 1965, TOPICS PHOSPHORUS CH, V2, P1

[8] PREPARATION OF SCALEMIC P-CHIRAL PHOSPHINES AND THEIR DERIVATIVES [J].

PIETRUSIEWICZ, KM ;

ZABLOCKA, M .

CHEMICAL REVIEWS, 1994, 94 (05) :1375-1411

[9]

Raushel FM, 2000, ADV ENZYMOL RAMB, V74, P51

[10] Bacterial detoxification of organophosphate nerve agents [J].

Raushel, FM .

CURRENT OPINION IN MICROBIOLOGY, 2002, 5 (03) :288-295