Acceptor-dependent stereoselective glycosylation: 2'-CB glycoside-mediated direct beta-D-arabinofuranosylation and efficient synthesis of the octaarabinofuranoside in mycobacterial cell wall.
[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.
Lee
Yong Joo
YJ
Center for Bioactive Molecular Hybrids and Department of Chemistry, Yonsei University, Seoul, Korea.
Lee
Kyunghoon
K
Jung
Eun Hye
EH
Jeon
Heung Bae
HB
Kim
Kwan Soo
KS
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
D006027:Glycosides