Argunov DA, Krylov VB, Nifantiev NE Convergent synthesis of isomeric heterosaccharides related to the fragments of galactomannan from Aspergillus fumigatus Organic and Biomolecular Chemistry13(11) (2015)
3255-3267
NCBI PubMed ID:25643073 Publication DOI:10.1039/c4ob02634a Journal NLM ID:101154995 Publisher: The Royal Society of Chemistry Correspondence: Nifantiev NE <nenioc.ac.ru> Institutions: Laboratory of Glycoconjugate Chemistry, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Laboratory of Glycoconjugate Chemistry, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prospect 47, Moscow, Russia
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 the galactomannan.
cell wall, Galactomannan, Aspergilus, antifungal drug target
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