Di-tert-butyl diethylphosphoramidite as the phosphitylating reagent in the preparation of 3-deoxy-3-C-methylene-D-ribo-hexose-6-phosphate and 3-deoxy-3-C-methylene-D-erythro-pentose-5-phosphate

被引:5
作者
Burger, A [1 ]
Tritsch, D [1 ]
Biellmann, JF [1 ]
机构
[1] Univ Strasbourg 1, Fac Chim, CNRS, UMR 7509,Lab Chim Organ Biol, F-67008 Strasbourg, France
关键词
carbohydrates; enzyme inhibitors; phosphoric acids and derivatives; phosphorylation;
D O I
10.1016/S0008-6215(01)00089-1
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
3-Deoxy-3-C-methylene-D-ribo-hexose-6-phosphate and 3-deoxy-3-C-methylene-D-erythro-pentose-5-phosphate were prepared from a common intermediate 3-deoxy-3-C-methylene-1,2-O-isopropylidene-alpha -D-ribo-hexofuranose.The preparation of the phosphorylated unsaturated sugars employed di-tert-butyl diethylphosphoramidite as the phosphitylating reagent. The removal of all the protecting groups was done under acidic conditions in the ultimate step. The unsaturated sugar phosphates were competitive inhibitors but neither substrates nor inactivators of glucose-6-phosphate and ribose-5-phosphate isomerases. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:141 / 149
页数:9
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