title: One-pot synthesis of branched oligosaccharides by use of galacto- and mannopyranosyl thioglycoside diols as key glycosylating agents.
abstract: We describe in this paper the efficient four-component one-pot synthesis of three fully protected oligosaccharides 22, 36, and 50 with di-branched structures by employing D-galacto- and mannopyranosyl thioglycoside diols as central glycosylating agents. After global deprotection, they were converted respectively into the 3-aminopropyl linker-containing free oligosaccharide fragments 14, 24, and 38 structurally related to cell wall oligosaccharides from Atractylodes lancea DC, the marine fungus Lineolata rhizophorae and pathogenic Mycobacterium tuberculosis. The 3-aminopropyl linker at the anomeric carbon can enable conjugation of these synthetic oligomers to a suitable protein carrier.
authors: Key Laboratory of Drug Targeting, Ministry of Education, and Department of Chemistry of Medicinal Natural Products, West China School of Pharmacy, Sichuan University, Chengdu 610041, P. R. China.
authors: Xing-Yong
authors: XY
authors: Liang
authors: Qiang-Wei
authors: QW
authors: Liu
authors: Hua-Chao
authors: HC
authors: Bin
authors: Jin-Song
authors: JS
authors: Yang
mesh_terms: D060326:Chemistry Techniques, Synthetic; D005690:Galactose / Q000737:chemistry*; D006031:Glycosylation; D008358:Mannose / Q000737:chemistry*; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity; D013865:Thioglycosides / Q000737:chemistry*
chemical_list: D009844:Oligosaccharides; D013865:Thioglycosides; D008358:Mannose; D005690:Galactose