ChemInform Abstract: Synthesis of New Serine-Linked Oligosaccharides in Blood-Clotting Factors VII and IX and Protein Z. The Syntheses of O-α-D- Xylopyranosyl-(1 → 3)-D-glucopyranose, O-α-D- Xylopyranosyl-(1 → 3)-O-α-D-xylopyranosyl-(1 → 3)- D-glucopyrano

Abstract

The di- and trisaccharide sequences and their conjugates with serine recently identified in the first epidermal growth factor-like domain of bovine and human blood-clotting factors VII, IX, and protein Z were synthesized in order to elucidate their biological function. The disaccharide α-D-Xylp(1→3)-D-Glcp was prepared from 2,3,4-tri-O-benzyl-α-D-xylopyranosyl fluoride and allyl 2,4,6-tri-O-acetyl-α-D-grucopyranoside (9a) using tin(II) chloride and silver perchlorate as glycosylating reagents. The trisaccharide α-D-Xylp(1→3)-α-D-Xylp(1→3)-D-Glcp was prepared from O-(2,3,4-tri-O-benzyl-α-D-xylopyranosyl)-(1→3)-2,4-di-O-benzyl-α,β-D-xylopyranosyl fluoride and 9a with the same reagents. Their conjugates with serine, α-D-Xylp(1→3)-β-D-Glcp(1→3)-L-Ser and α-D-Xylp(1→3)-α-D-Xylp(1→3)-β-D-Glcp(1→3)-L-Ser, were synthesized by the glycosylation of N-benzyloxycarbonyl-L-serine benzyl ester with the corresponding glycosyl trichloroacetimidates of the above saccharides, followed by removal of the protecting groups. T...