C-C Bond-Forming Lyases in Organic Synthesis

被引:179
作者
Brovetto, Margarita [1 ]
Gamenara, Daniela [1 ]
Saenz Mendez, Patricia [1 ,2 ]
Seoane, Gustavo A. [1 ]
机构
[1] Univ Republ UdelaR, Grp Fis Quim Organ & Bioproc, Dept Quim Organ, Montevideo 11800, Uruguay
[2] Univ Republ UdelaR, Fac Quim, DETEMA, Grp Quim & Biol Computac, Montevideo 11800, Uruguay
关键词
ENZYME-CATALYZED REACTIONS; N-ACETYLNEURAMINIC ACID; L-THREONINE ALDOLASE; ONE-POT SYNTHESIS; SITE-DIRECTED MUTAGENESIS; ALPHA-AMINO ACIDS; OPTICALLY-ACTIVE CYANOHYDRINS; DIPHOSPHATE-DEPENDENT ENZYMES; STEREOSELECTIVE BIOCATALYTIC SYNTHESIS; EFFICIENT CHEMOENZYMATIC SYNTHESIS;
D O I
10.1021/cr100299p
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Lyase catalyzed C-C bond formation is reviewed and an overview of the latest developments in the field of synthetic applications of enzymatic aldol, acyloin condensation, and cyanohydrin reactions, is presented. New insights on enzymatic mechanism and structure, added to an increasing number of synthetic applications has made possible the development of new catalysts and new reactions. The discovery of novel aldolase activity of promiscuous enzymes, and unexpected relaxed substrate specificity, has broadened the opportunities to perform enzymatic carboligations to solve synthetic problems. New techniques such as DYKAT, tandem aldol-Henry methods, or buffer trapping, have expanded the scope of biocatalytic methods. It is also found that more flexibility for the donor substrate is desirable for both aldolases and hydroxynitrilases. Improvements in the stereoselectivity of some enzymes are needed, in particular for TagA and ThrA.
引用
收藏
页码:4346 / 4403
页数:58
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