A chemoenzymatic synthesis of deoxy sugar esters involving stereoselective acetylation of hemiacetals catalyzed by CALB

被引：7

作者：

Villo, Ly ^{[1
]}

Kreen, Malle ^{[1
]}

Kudryashova, Marina ^{[1
]}

Metsala, Andrus ^{[1
]}

Tamp, Sven ^{[1
]}

Lille, Ulo ^{[1
]}

Pehk, Tonis ^{[2
]}

Parve, Omar ^{[1
]}

机构：

[1] Tallinn Univ Technol, Dept Chem, EE-12618 Tallinn, Estonia

[2] NICPB, Dept Chem Phys, EE-12618 Tallinn, Estonia

来源：

JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC | 2011年 / 68卷 / 01期

关键词：

Deoxy sugar ester; Chemoenzymatic synthesis; Lipase-catalyzed acetylation; Furanose and pyranose hemiacetal; N-Boc-amino acid ester; FATTY-ACIDS; LIPASE; DERIVATIVES; ACYLATION; ENZYME;

D O I：

10.1016/j.molcatb.2010.09.008

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

An extension of the scope of the chemoenzymatic strategy for the synthesis of stereochemically pure pyranose deoxy sugar esters of different carboxylic acids has been achieved The objective of the work was to extend the strategy to the synthesis of furanose deoxy sugar derivatives and additionally to N-Boc-protected amino acid esters With all used carboxylic acids (deoxycholic acid alpha-methoxyphenylacetic acid N-Boc-L-phenylalanine and N-Boc-L-tyrosine) the lipase-catalyzed stereoselecnve acetylation of furanose or pyranose hemiacetal moiety as a key step afforded one desired stereochemically pure acetylated hemiacetal deoxy sugar ester in high de (c) 2010 Elsevier B V All rights reserved

引用

页码：44 / 51

页数：8

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