Kinetic resolution of poly(ethylene glycol)-supported carbonates by enzymatic hydrolysis

被引：22
作者：
Nogawa, Masaki
Shimojo, Megumi
Matsumoto, Kazutsugu
Okudomi, Masayuki
Nemoto, Yuji
Ohta, Hiromichi
机构：
[1] Iwaki Meisei Univ, Dept Chem, Hino, Tokyo 1918506, Japan
[2] Keio Univ, Dept Biosci & Informat, Yokohama, Kanagawa 2238522, Japan
来源：
TETRAHEDRON | 2006年 / 62卷 / 31期
基金：
日本学术振兴会;
关键词：
carbonates; enantioselective hydrolysis; enzymes; hydrolase; poly(ethylene glycol)-supported substrate;
D O I：
10.1016/j.tet.2006.05.020
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The enzyme-mediated enantioselective hydrolysis of poly(ethylene glycol) (PEG)-supported carbonates is disclosed. The water-soluble carbonates were prepared by immobilization of a racemic secondary alcohol (4-benzyloxy-2-butanol) onto low-molecular weight (av MW 550 and 750) monometboxy PEG through a carbonate linker. For the screening of the hydrolytic enzymes, the substrate was enantioselectively hydrolyzed by commercially available lipase from porcine pancreas (PPL; Type II, Sigma) to afford the optically active compounds. In this system, the separation of the remaining (S)-substrate and the resulting (R)-alcohol was achieved by an extraction process without a laborious column chromatography. The (S)-carbonate was easily hydrolyzed with K2CO3 to afford the corresponding (S)-alcohol. Other MPEG-supported substrates were also hydrolyzed to afford the corresponding optically active alcohols. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码：7300 / 7306
页数：7
相关论文
共 50 条
[1]   Penicillin G amidase-catalysed hydrolysis of phenylacetic hydrazides on a solid phase: A new route to enzyme-cleavable linkers [J].
Basso, A ;
Ebert, C ;
Gardossi, L ;
Linda, P ;
Phuong, TT ;
Zhu, M ;
Wessjohann, L .
ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (7-8) :963-966
[2]   Introduction of permanently charged groups into PEGA resins leads to improved biotransformations on solid support [J].
Basso, A ;
Ulijn, RV ;
Flitsch, SL ;
Margetts, G ;
Brazendale, I ;
Ebert, C ;
De Martin, L ;
Linda, P ;
Verdelli, S ;
Gardossi, L .
TETRAHEDRON, 2004, 60 (03) :589-594
[3]   Enantiomeric partitioning using fluorous biphase methodology for lipase-mediated (trans)esterifications [J].
Beier, P ;
O'Hagan, D .
CHEMICAL COMMUNICATIONS, 2002, (16) :1680-1681
[4]  
Benaglia M, 2001, ADV SYNTH CATAL, V343, P171, DOI 10.1002/1615-4169(20010226)343:2<171::AID-ADSC171>3.3.CO
[5]  
2-V
[6]   Using soluble polymers to recover catalysts and ligands [J].
Bergbreiter, DE .
CHEMICAL REVIEWS, 2002, 102 (10) :3345-3383
[7]  
Bommarius A.S., 2004, BIOCATALYSIS
[8]  
Bornscheuer UT, 2006, HYDROLASES IN ORGANIC SYNTHESIS: REGIO- AND STEREOSELECTIVE BIOTRANSFORMATIONS, 2ND EDITION, P1
[9]   ENANTIOSELECTIVE ESTERIFICATIONS OF UNSATURATED ALCOHOLS MEDIATED BY A LIPASE PREPARED FROM PSEUDOMONAS SP [J].
BURGESS, K ;
JENNINGS, LD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (16) :6129-6139
[10]   Free-radical hydroxylation reactions of alkylboronates [J].
Cadot, C ;
Dalko, PI ;
Cossy, J ;
Ollivier, C ;
Chuard, R ;
Renaud, P .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (21) :7193-7202
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