期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 14, 期 30, 页码 9400-9411出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200800960
关键词
glycosylation; gulose; oligosaccharides; oxacarbenium ions; oxidation; thioglycosides
资金
- Council for Chemical Sciences of the Netherlands Organisation for Scientific Research (NWO)
The glycosylation properties of gulopyranosides have been mapped out, and it is shown that gulose has an intrinsic preference for the formation of 1,2-cis-glycosidic bonds. It is postulated that this glycosylation behaviour originates from nucleophilic attack at the oxacarbenium ion, which adopts the most favourable H-3(4) conformation. Building on the stereoselectivity of gulose, a guluronic acid alginate trisaccharide was assembled for the first time by using gulopyranosyl building blocks.
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