Base catalyzed racemization of amino acid derivatives

被引：19

作者：

D'Arrigo, Paola ^{[1
,2
,3
]}

Arosio, Dario ^{[1
]}

Cerioli, Lorenzo ^{[1
]}

Moscatelli, Davide ^{[1
]}

Servi, Stefano ^{[1
,2
,3
]}

Viani, Fiorenza ^{[4
]}

Tessaro, Davide ^{[1
,2
,3
]}

机构：

[1] Politecn Milan, Dept Chem Mat & Chem Engn Giulio Natta, I-20133 Milan, Italy

[2] Politecn Milan, Ctr Interuniv Ric Biotecnol Prot Prot Factory, I-20131 Milan, Italy

[3] Univ Insubria, I-20131 Milan, Italy

[4] CNR, ICRM, I-20131 Milan, Italy

来源：

TETRAHEDRON-ASYMMETRY | 2011年 / 22卷 / 08期

关键词：

DYNAMIC KINETIC RESOLUTION; AQUEOUS-SOLUTION; EQUILIBRIUM-CONSTANTS; ENZYMATIC RESOLUTION; ASYMMETRIC-SYNTHESIS; ORGANIC-COMPOUNDS; PROTON-TRANSFER; DERACEMIZATION; STEREOINVERSION; TRANSFORMATION;

D O I：

10.1016/j.tetasy.2011.05.005

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Amino acid thioesters used as substrates for a chemo-enzymatic dynamic kinetic resolution (DKR) must be designed with a high enough acidity to be rapidly racemized in the presence of a suitable base. Kinetic data obtained from experimental proton exchange rates are correlated with thermodynamic data for the proton abstraction based on the density functional theory (DFT) calculations. The good correlation obtained allows to evaluate the contribution of different functional groups to the carbon acidity and to define bases able to perform the required racemization. (C) 2011 Elsevier Ltd. All rights reserved,

引用

页码：851 / 856

页数：6

共 50 条

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