A novel chemical synthesis of a 3-deoxy-D-arabino-heptulosonic acid 7-phosphate (DAHP) derivative and its 2-deoxy analogue

被引：12

作者：

Mlynarski, J ^{[1
]}

Banaszek, A ^{[1
]}

机构：

[1] POLISH ACAD SCI,INST ORGAN CHEM,PL-01224 WARSAW,POLAND

来源：

CARBOHYDRATE RESEARCH | 1996年 / 295卷

关键词：

DAHP; D-arabino-heptulosonic acid; 2-deoxy-D-arabino-heptulosonic acid;

D O I：

10.1016/S0008-6215(96)90122-6

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：

Using 2,3,4,6-tetra O-acetyl-beta-D-glucopyranosyl cyanide as a precursor, methyl (methyl 3-deoxy-alpha-D-arabino-hept-2-ulopyranosid)onate (6) and its 2-deoxy analogue (10) were prepared. The synthesis involved an elimination of one molecule of acetic acid from C-2-C-3 and transformation of the CN group into COOMe, followed by methoxymercuration with subsequent reductive removal of the mercuri residue to give 6 or hydrogenation of the double bond to give 10. Phosphorylation of the 7-OH group led to the title compounds. (C) 1996 Elsevier Science Ltd.

引用

页码：69 / 75

页数：7

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