J. Dinkelaar, Leendert J van den Bos, W. Hogendorf
Oct 20, 2008
Citations
0
Influential Citations
36
Citations
Journal
Chemistry
Abstract
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 3H4 conformation. Building on the stereoselectivity of gulose, a guluronic acid alginate trisaccharide was assembled for the first time by using gulopyranosyl building blocks.