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Stereo‐ and Biochemical Profiles of the 5‐6‐ and 6‐6‐Junction Isomers of α ‐ D ‐Mannopyranosyl [60]Fullerenes
Author(s) -
Nishida Yoshihiro,
Mizuno Akiko,
Kato Haruhito,
Yashiro Arihiro,
Ohtake Tomoyuki,
Kobayashi Kazukiyo
Publication year - 2004
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.200490106
Subject(s) - chemistry , circular dichroism , aqueous solution , chloroform , fullerene , nuclear magnetic resonance spectroscopy , lectin , nmr spectra database , molecular dynamics , stereochemistry , spectral line , computational chemistry , organic chemistry , biochemistry , astronomy , physics
Abstract The 5‐6‐ and 6‐6‐junction isomers of α ‐ D ‐mannopyranosyl [60]fullerene were studied by means of circular dichroism (CD), deuterium labeling, 1 H‐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 1 H‐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.