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Convergent synthesis of isomeric heterosaccharides related to the fragments of galactomannan from Aspergillus fumigatus†
D. A. Argunov,V. B. Krylov,N. E. Nifantiev
Organic & Biomolecular Chemistry Pub Date : 01/22/2015 00:00:00 , DOI:10.1039/C4OB02634A
Abstract

Aspergillus fumigatus is a very common fungus with high pathogenic potential for immunosuppressed hospital patients. A. fumigatus galactomannan, being the part of its cell wall, is considered as a promising candidate for vaccine and diagnostic test-systems. In this article we report the convergent synthesis of pentasaccharide fragments of the galactomannan containing the β-(1→5)-linked galactofuranoside chain attached to O-3 or O-6 of a spacer-armed mannopyranoside residue. The synthesis of selectively protected galactofuranoside precursors has been performed using recently developed pyranoside-into-furanoside (PIF) rearrangement. For assembling the target galactomannan structures the [1 + 2 + 2]-scheme was applied. This strategy was shown to be highly efficient and can easily be extended to the synthesis of longer fragments of thegalactomannan.

Graphical abstract: Convergent synthesis of isomeric heterosaccharides related to the fragments of galactomannan from Aspergillus fumigatus
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