title: Acceptor-dependent stereoselective glycosylation: 2'-CB glycoside-mediated direct beta-D-arabinofuranosylation and efficient synthesis of the octaarabinofuranoside in mycobacterial cell wall.
abstract: [reaction: see text]. A reliable and generally applicable direct method for the stereoselective beta-arabinofuranosylation employing a 2'-carboxybenzyl arabinofuranoside as the glycosyl donor has been established. The acyl-protective group on glycosyl acceptors is essential for the beta-stereoselectivity. The power of the present acceptor-dependent glycosylation method was demonstrated by the efficient synthesis of the octaarabinofuranoside in arabinogalactan and lipoarabinomannan found in mycobacterial cell wall.
authors: Center for Bioactive Molecular Hybrids and Department of Chemistry, Yonsei University, Seoul, Korea.
authors: Yong Joo
authors: YJ
authors: Lee
authors: Kyunghoon
authors: K
authors: Lee
authors: Eun Hye
authors: EH
authors: Jung
authors: Heung Bae
authors: HB
authors: Jeon
authors: Kwan Soo
authors: KS
authors: Kim
mesh_terms: D002473:Cell Wall / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry*; D006031:Glycosylation; D015394:Molecular Structure; D009161:Mycobacterium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D006027:Glycosides