Chemical synthesis of cyclic galactooligofuranosides isolated from enzymatic degradation products of cell wall arabinogalactan of Mycobacterium tuberculosis.
Synthesis of cyclic tetra-, hexa- and octasaccharides containing alternating (1-->5)-beta- and (1-->6)-beta-galactofuranosyl linkages has been achieved by intramolecular cycloglycosylation of corresponding linear sugars and by cyclooligomerization of 1,6-linked and 1,5-linked disaccharides. In particular, cyclooligomerization of the (1-->6)-beta-galactofuranosyl disaccharide provides an efficient way to secure all three cyclic sugars in one operation.
Kim
Kwan Soo
KS
Center for Bioactive Molecular Hybrids and Department of Chemistry, Yonsei University, Seoul, Korea. kwan@yonsei.ac.kr
Lee
Bo-Young
BY
Yoon
Sung Ho
SH
Jeon
Hyo Jin
HJ
Baek
Ju Yuel
JY
Jeong
Kyu-Sung
KS
D002473:Cell Wall / Q000737:chemistry* / Q000378:metabolism; D003500:Cyclization; D005685:Galactans / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D015394:Molecular Structure; D009169:Mycobacterium tuberculosis / Q000737:chemistry* / Q000378:metabolism; D011135:Polysaccharides, Bacterial / Q000737:chemistry*; D013237:Stereoisomerism
D005685:Galactans; D011135:Polysaccharides, Bacterial; C005653:arabinogalactan