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
收藏
页码：938 / 944
页数：7
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