Shortcut synthesis of beta-cyclomannin from beta-cyclodextrin.
Beta-cyclomannin, a cyclic oligosaccharide consisting of seven alpha-D-mannosides connected together by the (1-->4) glycoside linkage, has been efficiently synthesized by the OsO4 oxidation of heptakis(2,3-didehydroxy)-beta-cyclodextrin which was prepared from beta-cyclodextrin by a five-step transformation. The novel cyclooligosaccharide not only showed water solubility high enough to meet the requirement for drug formulation but also demonstrated strong binding ability toward guest molecules. [reaction: see text]
Fukudome
Makoto
M
Department of Molecular Medicinal Sciences, Graduate School of Biomedical Sciences, Nagasaki University, Nagasaki 852-8521, Japan.
Shiratani
Tomonori
T
Nogami
Yasuyoshi
Y
Yuan
De-Qi
DQ
Fujita
Kahee
K
D006860:Hydrogen Bonding; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008362:Mannosides / Q000138:chemical synthesis*; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D010084:Oxidation-Reduction; D013056:Spectrophotometry, Ultraviolet; D047392:beta-Cyclodextrins / Q000737:chemistry*
D007202:Indicators and Reagents; D008362:Mannosides; D009844:Oligosaccharides; D047392:beta-Cyclodextrins; C522313:beta-cyclomannin