Biocatalyzed Enantioselective Reduction of Activated C=C Bonds: Synthesis of Enantiomerically Enriched α-Halo-β-arylpropionic Acids

被引：29

作者：

Brenna, Elisabetta ^{[1
]}

Gatti, Francesco G. ^{[1
]}

Manfredi, Alessia ^{[1
]}

Monti, Daniela ^{[2
]}

Parmeggiani, Fabio ^{[1
]}

机构：

[1] Politecn Milan, Dipartimento Chim, I-20131 Milan, Italy

[2] CNR, Ist Chim Riconoscimento Mol, I-20131 Milan, Italy

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 2011卷 / 20-21期

关键词：

Enzyme catalysis; Biocatalysis; Reduction; Asymmetric synthesis; Biotransformations; OLD YELLOW ENZYME; AMINO-ACIDS; ASYMMETRIC HYDROGENATION; FAMILY; YEAST; EFFICIENT; DERIVATIVES; INHIBITORS; RESOLUTION; DISCOVERY;

D O I：

10.1002/ejoc.201100537

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The enantioselective biocatalyzed reduction of the C=C bond of some (Z)-methyl alpha-halo-beta-arylacrylates was investigated. The reaction was performed by baker's yeast fermentation and Old Yellow Enzymes 1-3 mediated biotransformations. The final products were, respectively, enantiomerically enriched (S)-alpha-halo-beta-arylpropionic acids and their methyl esters, and ester hydrolysis was promoted in the whole cell system. High conversions and enantioselectivity values were observed when the aromatic ring was substituted by an electron-withdrawing group. Further manipulation of two of these enantiomerically enriched (S)-haloacids afforded p-substituted D-phenylalanines.

引用

页码：4015 / 4022

页数：8

共 77 条

[1] Novel biosynthetic routes to non-proteinogenic amino acids as chiral pharmaceutical intermediates [J].

Ager, DJ ;

Li, T ;

Pantaleone, DP ;

Senkpeil, RF ;

Taylor, PP ;

Fotheringham, IG .

JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2001, 11 (4-6) :199-205

[2] Hydantoinases and related enzymes as biocatalysts for the synthesis of unnatural chiral amino acids [J].

Altenbuchner, J ;

Siemann-Herzberg, M ;

Syldatk, C .

CURRENT OPINION IN BIOTECHNOLOGY, 2001, 12 (06) :559-563

[3]

Barba O., 2010, WO Pat. Appl., Patent No. 2010103335

[4] (Z)-α-haloacrylates:: An exceptionally stereoselective preparation via Cr(II)-mediated olefination of aldehydes with trihaloacetates [J].

Barma, DK ;

Kundu, A ;

Zhang, HM ;

Mioskowski, C ;

Falck, JR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (11) :3218-3219

[5]

Bechtold M., ORG PROC RES D UNPUB

[6]

Betancort J. M., 2010, [No title captured], Patent No. [2010/33466 A1, 201033466]

[7]

Bjoere A., 2004, [No title captured], Patent No. [1192154 B1, 1192154]

[8]

Blaser H.-U., 2007, REND LINCEI-SCI FIS, V18, P281, DOI DOI 10.1007/BF02934925

[9] From a chiral switch to a ligand portfolio for asymmetric catalysis [J].

Blaser, Hans-Ulrich ;

Pugin, Benoit ;

Spindler, Felix ;

Thommen, Marc .

ACCOUNTS OF CHEMICAL RESEARCH, 2007, 40 (12) :1240-1250

[10]

Bommarius AS, 2001, CHIMIA, V55, P50

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