Synthetic α,β-(1→4)-Glucan Oligosaccharides as Models for Heparan Sulfate. Part II
| Autor: | Hans Peter Wessel, Rudolf E. Minder, Gerhard Englert |
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| Rok vydání: | 1996 |
| Předmět: | |
| Zdroj: | Journal of Carbohydrate Chemistry. 15:201-216 |
| ISSN: | 1532-2327 0732-8303 |
| DOI: | 10.1080/07328309608005439 |
| Popis: | α,β-(1→4)-Glucan oligosaccharides were prepared 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 saccharides were synthesized using maltosyl building blocks. Glycosylation of methyl 2,3,6-tri-O-benzyl-α-D-glucopyranoside (1) with hepta-O-acetyl-α-maltosyl bromide (2) furnished trisaccharide 3 which was deprotected to α-D-Glc-(1→4)-β-D-Glc-(1→4)-α-D-Glc(1→OCH3) (5) or, alternatively, converted to the trisaccharide glycosyl acceptor (8) with one free hydroxyl function (4″-OH). Further silver triflate mediated glycosylation with glucosyl or maltosyl bromide followed by deblocking gave the tetrasaccharide β-D-Glc-(1→4)-α-D-Glc-(1→4)-β-D-Glc-(1→4)-α-D-Glc-(1→OCH3) (11) and the pentasaccharide [α-D-Glc-(1→4)-β-D-Glc-(1→4)]2-α-D-Glc-(1→OCH3) (14). The trisaccharides 3, 4, 6, and 8 as well as pentasacchari... |
| Databáze: | OpenAIRE |
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