期刊
CARBOHYDRATE RESEARCH
卷 337, 期 21-23, 页码 1893-1916出版社
ELSEVIER SCI LTD
DOI: 10.1016/S0008-6215(02)00299-9
关键词
glucosamines; glycosyl phosphates; automated solid-phase synthesis
资金
- NCRR NIH HHS [1S10RR13886-01] Funding Source: Medline
Glucosamines are common components of many biologically important oligosaccharides. Reported is a systematic evaluation of glucosamine phosphates and trichloroacetimidates as glycosylating agents for the efficient construction of beta-(1 --> 6) glucosamine linkages. A set of differentially protected glucosamine donors incorporating a host of amine protecting groups, including 2-phthaloyl, benzyloxycarbonyl (Z), trichloroetheoxycarbonyl (Troc) and trichloroacetyl (TCA) protective groups. were prepared. Donors were initially evaluated for reactivity and protecting group compatibility in a solution-phase study with a model 6-hydroxyl galactose acceptor. Based on these results, glucosamine donor 10 was selected for the solution-phase synthesis of a beta-(1 --> 6)-glucosamine pentasaccharide. Finally, building block 10 proved well suited for use in the automated solid-phase synthesis of a repeating unit trisaccharide. An assessment of glucosamine phosphate donors as potential glycosylating agents for a variety of glucosamine linkages is also discussed. (C) 2002 Elsevier Science Ltd. All rights reserved.
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