A highly convergent synthesis of a hexasaccharide derived from the oligosaccharide of group B type III Streptococcus
β Scribed by Alexei Demchenko; Geert-Jan Boons
- Publisher
- Elsevier Science
- Year
- 1997
- Tongue
- French
- Weight
- 254 KB
- Volume
- 38
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
We have developed a novel glycosylation strategy which enabled a highly convergent assembly of a hexasaccharide derived from group B type I11 Streptococcus.
π SIMILAR VOLUMES
A convergent synthesis of a hexasaccharide corresponding to the cell-wall polysaccharide of the &hemolytic Streptococcus Group A is described. The strategy relies on the preparation of a key linear trisaccharide unit f3-D-GlcpNAc-(1 --) 3)-cY-r\_-Rhap\_(l + 2)-o-L-Rhap which has previously resisted
Syntheses of the propyl glycosides (1-3) of beta-D-Galp-(1----4)-beta-D-GlcpNAc, beta-D-Glcp-(1----6)-[beta-D-Galp-(1----4)]-beta-D-GlcpNAc, and beta-D-Galp-(1----4)-beta-D-Glcp-(1----6)-[beta-D-Galp-(1----)]-beta-D- GlcpNAc, respectively, are reported. Reaction of allyl 2-acetamido-3-O-benzyl-2-deo
Building block derivatives of the component monosaccharides were used to construct the tetrasaccharide glycoside 15, in which an alpha-D-Galp-(1 leads to 4)-D-Gal linkage replaces the alpha-(1 leads to 3) linkage of the human blood-group B, type 2, determinant structure. The initial coupling of 2-O-
Syntheses of methyl 2-O-&I\_-rhamnopyranosyl-PD-galactopyranoside (9), methyl 2-O-cr-L-rhamnopyranosyl-/3-D-galactopyranoside (l3), and methyl 4-O-/3-D-glucopyranosyl-2-O-a-L-rhamnopyranosyl-BD-galactopyranoside ( 16) in good yields are described. Both 13 and 16 significantly inhibit antigen-antibod