Stereo- and biochemical profiles of the 5-6- and 6-6-junction isomers of alpha-D-mannopyranosyl [60]fullerenes.
The 5-6- and 6-6-junction isomers of alpha-D-mannopyranosyl [60]fullerene were studied by means of circular dichroism (CD), deuterium labeling, 1H-NMR, molecular-dynamics (MD) calculations, and a lectin-binding assay. The CD spectra of the O-acetylated derivatives allowed clear discrimination of the isomers, while the 1H-NMR spectra, with assistance from deuterium labeling and MD calculations, served to disclose the unique conformation and molecular geometry of each acetylated isomer in chloroform solution. The deprotected 5-6- and 6-6-isomers, which gave colloidal suspensions in aqueous mixtures, displayed marked activity in blocking lectin-induced hemagglutination by concanavalin A.
Nishida
Yoshihiro
Y
Department of Molecular Design & Engineering, Graduate School of Engineering, Nagoya University, Chikusa-ku, Nagoya 464-8603, Japan. nishida@mol.nagoya-u.ac.jp
Mizuno
Akiko
A
Kato
Haruhito
H
Yashiro
Arihiro
A
Ohtake
Tomoyuki
T
Kobayashi
Kazukiyo
K
D002236:Carbohydrate Conformation; D037741:Fullerenes / Q000737:chemistry*; D008358:Mannose / Q000737:chemistry*; D011714:Pyrans / Q000737:chemistry*; D013237:Stereoisomerism
D037741:Fullerenes; D011714:Pyrans; D008358:Mannose