FORMATION OF DISACCHARIDES RELATED TO HEPARIN AND HEPARAN-SULFATE BY CHEMICAL MODIFICATION OF MALTOSE
FORMATION OF DISACCHARIDES RELATED TO HEPARIN AND HEPARAN-SULFATE BY CHEMICAL MODIFICATION OF MALTOSE
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DOI：
10.1016/0008-6215(90)80149-w
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发表时间：
1990-09-19
影响因子：
3.1
通讯作者：
PERLIN, AS
中科院分区：
文献类型：
--
作者：
GLUSHKA, JN;PERLIN, AS
Maltose has been converted into 4-O-(2-amino-2-deoxy-.alpha.-D-glucopyranosyl)-L-idopyranuronic acid, 4-O-(2-amino-2-deoxy-.alpha.-D-glucopyranosyl)-D-glucopyranose, and 4-O-.alpha.-D-glucopyranosyl-L-idopyranose, the first two disaccharides being related structurally to biose sequences in heparin and heparan sulfate. Used as the starting material was a major product of the kinetic acetonation of maltose, namely, 2,3:5,6-di-O-isopropylidene-4-O-(4,6-O-isopropylidene-.alpha.-D-glucopyranosyl)-aldehydo-D-glucose dimethyl acetal. It was subjected to a sequence of transformations that included the introduction of a 2''-amino-2''-deoxy function into the glucosyl group, the inversion of C-5 in the glucose residue to give the L-ido configuration, oxidation at position 6, and cyclisation of the acyclic dimethyl acetal to give the desired pyranuronic acid. In the formation of the latter, the 5-O-levulinoyl substituent was found to be less prone to acyl migration to O-6 than more conventional ester groups. The relative acid labilities of the O-isopropylidene and dimethyl acetal groups are compared, and conformations of the acyclic residues of some disaccharide derivatives are discussed.
