N-酰基和N-烷基-2-氨基-2-脱氧己糖对N-乙酰神经氨酸体外生物合成的抑制作用。

Inhibition of in vitro biosynthesis of N-acetylneuraminic acid by N-acyl- and N-alkyl-2-amino-2-deoxyhexoses.

作者信息

Grünholz H J, Harms E, Opetz M, Reutter W, Cerný M

出版信息

Carbohydr Res. 1981 Oct 16;96(2):259-70. doi: 10.1016/s0008-6215(00)81876-5.

Abstract

The biosynthesis of N-acetylneuraminic acid is markedly inhibited by 2-deoxy-2-propionamido-D-glucose (GlcNProp) and to a much lesser extent by 2-deoxy-2-propionamido-D-mannose (ManNProp), but not by 2-deoxy-2-propionamido-D-galactose and N-methylated derivatives of 2-amino-2-deoxy-D-glucose. 2-Deoxy-2-trimethylamino-D-glucose is a weak inhibitor of 2-acetamido-2-deoxy-D-mannose metabolism. When incubated in a cell-free system from rat liver, GlcNProp gives the 6-phosphate, which is converted into N-propionylneuraminic acid. Evidence is presented which shows that it is the metabolites GlcNProp-6-P and ManNProp-6-P which are the competitive inhibitors, and not GlcNProp itself.

摘要

2-脱氧-2-丙酰胺基-D-葡萄糖（GlcNProp）可显著抑制N-乙酰神经氨酸的生物合成，2-脱氧-2-丙酰胺基-D-甘露糖（ManNProp）的抑制作用则小得多，而2-脱氧-2-丙酰胺基-D-半乳糖和2-氨基-2-脱氧-D-葡萄糖的N-甲基化衍生物则无此作用。2-脱氧-2-三甲基氨基-D-葡萄糖是2-乙酰氨基-2-脱氧-D-甘露糖代谢的弱抑制剂。当在大鼠肝脏的无细胞系统中孵育时，GlcNProp会生成6-磷酸酯，后者可转化为N-丙酰神经氨酸。有证据表明，竞争性抑制剂是代谢产物GlcNProp-6-P和ManNProp-6-P，而非GlcNProp本身。