title: Convergent synthesis of isomeric heterosaccharides related to the fragments of galactomannan from Aspergillus fumigatus.
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.
authors: Laboratory of Glycoconjugate Chemistry, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prospect 47, 119991 Moscow, Russian Federation. nen@ioc.ac.ru.
authors: D A
authors: DA
authors: Argunov
authors: V B
authors: VB
authors: Krylov
authors: N E
authors: NE
authors: Nifantiev
mesh_terms: D001232:Aspergillus fumigatus / Q000737:chemistry*; D002236:Carbohydrate Conformation; D005690:Galactose / Q000031:analogs & derivatives; D008351:Mannans / Q000737:chemistry*; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D008351:Mannans; D009844:Oligosaccharides; C012990:galactomannan; D005690:Galactose