Naphthyl-L-α-amino acids via chemo-enzymatic dynamic kinetic resolution

被引：34

作者：

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

Cerioli, Lorenzo ^{[1
]}

Fiorati, Andrea ^{[1
]}

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

Viani, Fiorenza ^{[4
]}

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

机构：

[1] Politecn Milan, Dipartimento Chim Mat & Ingn Chim Giulio Natta, I-20133 Milan, Italy

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

[3] CNR Milano, ICRM, I-20131 Milan, Italy

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

来源：

TETRAHEDRON-ASYMMETRY | 2012年 / 23卷 / 13期

关键词：

3,5-DINITROBENZOIC ACID; ASYMMETRIC HYDROLYSIS; ENZYMATIC RESOLUTION; OPTICAL RESOLUTION; ANALOGS; ANTAGONISTS; DESIGN; ESTERS; 3-(2-NAPHTHYL)-L-ALANINE; (R)-1-NAPHTHYLGLYCINE;

D O I：

10.1016/j.tetasy.2012.06.020

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A double catalyst system (protease + base) was applied to the dynamic kinetic resolution (DKR) of isomeric 1- and 2-alpha-naphthyl-glycines and -alanines exploiting the in situ racemization of their thioesters. Due to the different C-acidity of the two sets of compounds, different experimental conditions have been devised to perform the simultaneous resolution/racemization process. In all cases, the racemic N-Boc-thioesters were converted into the aminoacids with an L-configuration almost quantitatively and with complete enantioselectivity. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：938 / 944

页数：7

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