Stereoselective synthesis of L-guluronic acid alginates.
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.
Dinkelaar
Jasper
J
Leiden Institute of Chemistry, Leiden University, P.O. Box 9502, 2300 RA Leiden, The Netherlands.
van den Bos
Leendert J
LJ
Hogendorf
Wouter F J
WF
Lodder
Gerrit
G
Overkleeft
Herman S
HS
Codée
Jeroen D C
JD
van der Marel
Gijsbert A
GA
D000464:Alginates / Q000138:chemical synthesis* / Q000737:chemistry; D004952:Esters / Q000737:chemistry; D005947:Glucose / Q000737:chemistry; D006031:Glycosylation; D006603:Hexuronic Acids / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
D000464:Alginates; D004952:Esters; D006603:Hexuronic Acids; C007896:guluronic acid; D005947:Glucose