1097178-52-3Relevant academic research and scientific papers
Stereoselective synthesis of L-guluronic acid alginates
Dinkelaar, Jasper,Van Den Bos, Leendert J.,Hogendorf, Wouter F. J.,Lodder, Gerrit,Overkleeft, Herman S.,Codee, Jeroen D. C.,Van Der Marel, Gijsbert A.
experimental part, p. 9400 - 9411 (2009/09/06)
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.
