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Convergent synthesis of an elusive hexasaccharide corresponding to the cell-wall polysaccharide of the β-hemolytic Streptococcus Group A

✍ Scribed by Jose-R. Marino-Albernas; Shannon L. Harris; Vikram Varma; B.Mario Pinto

Publisher
Elsevier Science
Year
1993
Tongue
English
Weight
786 KB
Volume
245
Category
Article
ISSN
0008-6215

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✦ Synopsis

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 our efforts. The trisaccharide functions both as a glycosyl acceptor and donor to give an elusive hexasaccharide. This fully functionalized unit can serve, in turn, as a glycosyl acceptor or donor for the synthesis of higher-order structures. Deprotection gives a hitherto unknown hexasaccharide for use as a hapten in immunochemical studies. The characterization of all compounds by high-resolution 'H and 13C NMR spectroscopy is also described.

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