Stereoselective C-C bond formation catalysed by engineered carboxymethylproline synthases

被引：0
|
作者：
Hamed R.B. [1 ,2 ]
Gomez-Castellanos J.R. [1 ]
Thalhammer A. [1 ]
Harding D. [1 ]
Ducho C. [1 ,3 ]
Claridge T.D.W. [1 ]
Schofield C.J. [1 ]
机构：
[1] Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Oxford OX1 3TA, Mansfield Road
[2] Department of Pharmacognosy, Faculty of Pharmacy, Assiut University
[3] Department of Chemistry, Institute of Organic and Biomolecular Chemistry, Georg-August-University Göttingen, Göttingen
来源：
Nature Chemistry | 2011年 / 3卷 / 5期
基金：
英国生物技术与生命科学研究理事会;
关键词：
D O I：
10.1038/nchem.1011
中图分类号：
学科分类号：
摘要：
The reaction of enol(ate)s with electrophiles is used extensively in organic synthesis for stereoselective C-C bond formation. Protein-based catalysts have had comparatively limited application for the stereoselective formation of C-C bonds of choice via enolate chemistry. We describe protein engineering studies on 5-carboxymethylproline synthases, members of the crotonase superfamily, aimed at enabling stereoselective C-C bond formation leading to N-heterocycles via control of trisubstituted enolate intermediates. Active site substitutions, including at the oxyanion binding site, enable the production of substituted N-heterocycles in high diastereomeric excesses via stereocontrolled enolate formation and reaction. The results reveal the potential of the ubiquitous crotonase superfamily as adaptable catalysts for the control of enolate chemistry. © 2011 Macmillan Publishers Limited. All rights reserved.
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页码：365 / 371
页数：6
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