Stereoselective synthesis of a fragment of mycobacterial arabinan.
Strategies for the stereoselective synthesis of mycobacterial arabinan were explored. Arabinofuranosyl donors with various protective groups were screened in terms of suitability for beta-(1,2-cis)-selective glycosylation. The protective group was found to affect the stereoselectivity of arabinofuranosylation. Beta-selectivity was drastically enhanced by using donors protected with 3,5-TIDPS, possibly due to conformational constraints on the furanose ring. Synthesis of heptaarabinofuranoside was then performed to demonstrate the practicality of this methodology. [reaction: see text].
Ishiwata
Akihiro
A
RIKEN (Institute of Physical and Chemical Research), Wako-shi, Saitama 351-0198, Japan.
Akao
Hiroko
H
Ito
Yukishige
Y
D002240:Carbohydrate Sequence; D002473:Cell Wall / Q000737:chemistry; D006031:Glycosylation; D008968:Molecular Conformation; D009161:Mycobacterium / Q000737:chemistry*; D011134:Polysaccharides / Q000138:chemical synthesis*; D013237:Stereoisomerism
D011134:Polysaccharides; C030080:araban