Rabbit muscle aldolase (RAMA) as a catalyst in a new approach for the synthesis of 3-deoxy-D-manno-2-octulosonic acid and analogues

被引:14
作者
Crestia, D [1 ]
Guérard, C [1 ]
Bolte, J [1 ]
Demuynck, C [1 ]
机构
[1] Univ Blaise Pascal, Lab Chim Org Biol, UMR CNRS 6504, F-63177 Clermont Ferrand, France
关键词
carbon-carbon bond formation; aldolase; KDO; KDO analogues;
D O I
10.1016/S1381-1177(00)00074-6
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
A new approach leading to 3-deoxy-D-manno-2-octulosonic acid (KDO) and 4-deoxy-KDO is described. The key step is the formation of the C-5-C-6 bond catalysed by fructose-1,6-bisphosphate aldolase, which controls the stereochemistry of these two centres. The important step of the aldehyde substrates (la, Ib, Ic) synthesis is the Barbier reaction of ethyl-bromomethylacrylate or bromomethylacrylonitrile with the monoacetal of glyoxal in the presence of indium. (C) 2001 Elsevier Science B.V. All rights reserved.
引用
收藏
页码:207 / 212
页数:6
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