Synthetic α,β(1→4)-Glucan Oligosaccharides as Models for Heparan Sulfate
| Autor: | Rudolf E. Minder, Gerhard Englert, Hans Peter Wessel |
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| Rok vydání: | 1995 |
| Předmět: | |
| Zdroj: | Journal of Carbohydrate Chemistry. 14:1101-1115 |
| ISSN: | 1532-2327 0732-8303 |
| DOI: | 10.1080/07328309508005398 |
| Popis: | α,β-(1→4)-Glucans were devised as models for heparan sulfate with the simplifying assumptions that carboxyl-reduction and sulfation of heparan sulfate does not decrease the SMC antiproliferative activity and that N-sulfates in glucosamines can be replaced by O-sulfates. The target oligo-saccharides were synthesized using maltosyl building blocks. Glycosylation of methyl 2,3,6,2′,3′,6′-hexa-O-benzyl-β-maltoside (1) with hepta-O-acetyl-α-maltosyl bromide (2) furnished tetrasaccharide 3 which was deprotected to α-D-Glc-(1→4)-β-D-Glc-(1→4)-α-D-Glc-(1→4)-β-D-Glc-(1→OCH3) (5) or, alternatively, converted to the tetrasaccharide glycosyl acceptor (8) with one free hydroxyl function (4‴′-OH). Further glycosylation with glucosyl or maltosyl bromide followed by deblocking gave the pentasaccharide [β-D-Glc-(1→4)-α-D-Glc-(1→4)]2-β-D-Glc-(1→OCH3) (11) and hexasaccharide [α-D-Glc-(1→4)-β-D-Glc-(1→4)2-α-D-Glc-(1→4)-β-D-Glc-(1→OCH3) (14). The protected tetrasaccharide 3 and hexasaccharide 12 were fully characteri... |
| Databáze: | OpenAIRE |
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