De novo chemoenzymatic synthesis of sialic acid

被引：10

作者：

Stallforth, Pierre ^{[1
,2
]}

Matthies, Stefan ^{[1
,2
]}

Adibekian, Alexander ^{[1
,2
]}

Gillingham, Dennis G. ^{[3
]}

Hilvert, Donald ^{[3
]}

Seeberger, Peter H. ^{[1
,2
]}

机构：

[1] Max Planck Inst Colloids & Interfaces, Dept Biomol Syst, D-14476 Potsdam, Germany

[2] Free Univ Berlin, D-14195 Berlin, Germany

[3] ETH, Organ Chem Lab, CH-8093 Zurich, Switzerland

来源：

CHEMICAL COMMUNICATIONS | 2012年 / 48卷 / 98期

关键词：

ALPHA-AMINO ALDEHYDES; N-ACETYLNEURAMINIC ACID; MACROPHOMATE SYNTHASE; CARBOHYDRATE MIMETICS; NEURAMINIC ACID; OLIGOSACCHARIDES; SPECTROSCOPY; DIVERSITY; ANALOGS; KETO;

D O I：

10.1039/c2cc37305j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A chemoenzymatic synthesis of sialic acid from inexpensive N-acetyl-D-glucosamine is described. In a three-step Wittig-protection-ozonolysis strategy manno-configured aldehydes are obtained. Treatment with oxaloacetate in the presence of macrophomate synthase affords the signature alpha-keto-gamma-hydroxy acid moiety with high diastereoselectivity.

引用

页码：11987 / 11989

页数：3

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