Chemoenzymatic synthesis of CMP-N-acetyl-7-fluoro-7-deoxy-neuraminic acid

被引：22

作者：

Hartlieb, Sina

Guenzel, Almut ^{[2
]}

Gerardy-Schahn, Rita ^{[2
]}

Muenster-Kuehnel, Anja K. ^{[2
]}

Kirschning, Andreas

Drager, Gerald ^{[1
]}

机构：

[1] Gottfried Wihelm Leibniz Univ Hannover, Inst Organ Chem, D-30167 Hannover, Germany

[2] Hannover Med Sch, Dept Cellular Chem, D-30625 Hannover, Germany

来源：

CARBOHYDRATE RESEARCH | 2008年 / 343卷 / 12期

关键词：

CMP-7-F-sialic acid; chemoenzymatic synthesis; sugar nucleotide;

D O I：

10.1016/j.carres.2008.02.003

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：

7-Fluoro sialic acid was prepared and activated as cytidine monophosphate (CMP) ester. The synthesis started with D-glucose, which was efficiently converted into N-acetyl-4-fluoro-4-deoxy-D-mannosamine. Aldolase catalyzed transformation yielded the corresponding fluorinated sialic acid which was activated as CMP ester using three different synthetases in the presence as well as in the absence of pyrophosphatase which possesses inhibitory properties. Finally, conditions were optimized to perform a one-pot reaction starting from fluorinated mannosamine, which yielded the 7-fluoro-7-deoxy-CMP-sialic acid by incubation with three enzymes. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：2075 / 2082

页数：8

共 35 条

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