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

Convergent synthesis of isomeric heterosaccharides related to the fragments of galactomannan from Aspergillus fumigatus Full article

Journal

Organic & Biomolecular Chemistry
ISSN: 1477-0520 , E-ISSN: 1477-0539

Output data

Year: 2015, Volume: 13, Number: 11, Pages: 3255-3267 Pages count : 13 DOI: 10.1039/c4ob02634a

Authors

Argunov D.A. ¹ , Krylov V.B. ¹ , Nifantiev N.E. ¹

Affiliations

1	Laboratory of Glycoconjugate Chemistry, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prospect 47, 119991 Moscow, Russian Federation

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.

Argunov D.A. , Krylov V.B. , Nifantiev N.E.
Convergent synthesis of isomeric heterosaccharides related to the fragments of galactomannan from Aspergillus fumigatus
Organic & Biomolecular Chemistry. 2015. V.13. N11. P.3255-3267. DOI: 10.1039/c4ob02634a WOS Scopus OpenAlex

≡ Web of science:	WOS:000351062700014
≡ Scopus:	2-s2.0-84924710204
≡ OpenAlex:	W1998119598