Synthesis of the alpha-D-GlcpA-(1-->3)-alpha-L-Rhap-(1-->2)-L-Rha trisaccharide isolated from the cell wall hydrolyzate of the green alga, Chlorella vulgaris.
The title trisaccharide was synthesized from 6-O-acetyl-2,3,4-tri-O-benzyl-alpha-D-glucopyranosyl chloride (10), ethyl 2,4-di-O-benzyl-1-thio- (5) and benzyl 3,4-di-O-benzyl-alpha-L-rhamnopyranoside (9). The disaccharide 11 obtained from compounds 5 and 10 was used as the glycosyl donor to glycosylate the rhamnopyranoside derivative 9 having free OH-2 using the NIS-AgOTf-mediated glycosylation methodology. Zemplén deacetylation of the trisaccharide 12 resulted in the 6"-OH derivative (13), which was selectively oxidized with CrO3 to the uronic acid derivative 14. The benzyl groups were removed by catalytic hydrogenolysis to furnish the target trisaccharide (1).
Sajtos
F
F
Research Group for Carbohydrates of the Hungarian Academy of Sciences, PO Box 55, H-4010, Debrecen, Hungary.
Hajkó
J
J
Kövér
K E
KE
Lipták
A
A
D002240:Carbohydrate Sequence; D002458:Cell Fractionation; D002473:Cell Wall / Q000737:chemistry*; D002708:Chlorella / Q000737:chemistry*; D004187:Disaccharides / Q000302:isolation & purification / Q000378:metabolism; D006868:Hydrolysis; D008969:Molecular Sequence Data; D014312:Trisaccharides / Q000138:chemical synthesis* / Q000302:isolation & purification
D004187:Disaccharides; D014312:Trisaccharides; C438443:glucopyranuronosyl-(1-3)-rhamnopyranosyl-(1-2)-rhamnopyranose