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蛋白酶催化的有机相不对称 Mannich 反应。

Protease-catalysed direct asymmetric Mannich reaction in organic solvent.

机构信息

School of Chemistry and Chemical Engineering, Southwest University , Chongqing, 400715, P. R. China.

出版信息

Sci Rep. 2012;2:761. doi: 10.1038/srep00761. Epub 2012 Oct 23.

Abstract

We reported the first enzyme-catalysed, direct, three-component asymmetric Mannich reaction using protease type XIV from Streptomyces griseus (SGP) in acetonitrile. Yields of up to 92% with enantioselectivities of up to 88% e.e. and diastereoselectivities of up to 92:8 (syn:anti) were achieved under the optimised conditions. This enzyme's catalytic promiscuity expands the application of this biocatalyst and provides a potential alternative method for asymmetric Mannich reactions.

摘要

我们报道了首例使用灰色链霉菌(Streptomyces griseus)蛋白酶 XIV 在乙腈中进行的酶催化、直接、三元不对称曼尼希反应。在优化条件下,最高产率可达 92%,对映选择性最高可达 88%ee,非对映选择性最高可达 92:8(syn:anti)。该酶的催化混杂性扩展了该生物催化剂的应用,并为不对称曼尼希反应提供了一种潜在的替代方法。

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本文引用的文献

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Modern Variants of the Mannich Reaction.曼尼希反应的现代变体
Angew Chem Int Ed Engl. 1998 May 4;37(8):1044-1070. doi: 10.1002/(SICI)1521-3773(19980504)37:8<1044::AID-ANIE1044>3.0.CO;2-E.
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Racemase activity of B. cepacia lipase leads to dual-function asymmetric dynamic kinetic resolution of α-aminonitriles.
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Enzyme promiscuity: a mechanistic and evolutionary perspective.酶的多功能性:一种机制和进化的观点。
Annu Rev Biochem. 2010;79:471-505. doi: 10.1146/annurev-biochem-030409-143718.
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What makes an enzyme promiscuous?是什么使酶具有混杂性?
Curr Opin Chem Biol. 2010 Apr;14(2):200-7. doi: 10.1016/j.cbpa.2009.11.028. Epub 2010 Jan 18.
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Enzyme promiscuity: evolutionary and mechanistic aspects.酶的多效性:进化与机制方面
Curr Opin Chem Biol. 2006 Oct;10(5):498-508. doi: 10.1016/j.cbpa.2006.08.011. Epub 2006 Aug 30.
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