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Spectrum–Structure Relationship in Carbohydrate Vibrational Circular Dichroism and Its Application to Glycoconjugates
Author(s) -
Taniguchi Tohru,
Monde Kenji
Publication year - 2007
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.200700180
Subject(s) - vibrational circular dichroism , glycoconjugate , pyranose , chemistry , glycosidic bond , circular dichroism , carbohydrate , computational chemistry , crystallography , anomer , density functional theory , carbohydrate conformation , stereochemistry , nuclear magnetic resonance spectroscopy , organic chemistry , biochemistry , enzyme
Preliminary reports of the nature of the vibrational circular dichroism (VCD) peak at around 1145 cm −1 , which is characteristic of axial glycosidic sugars and is called the glycoside band ( J. Am. Chem. Soc. 2004 , 126 , 9496), have been throughly examined. Through systematic carbohydrate measurements, it was found that the sign of the glycoside band reflects not only the anomeric configuration but also the pyranose conformation. Isotope and theoretical studies characterized its vibrational mode as C1–H1 deformation coupled with C1–O1 stretching, which indicates its applicability to more‐complicated glycoconjugates. In this study, for the first time, carbohydrate VCD spectra were reliably predicted by means of density functional theory (DFT) calculations. The VCD technique was applied to glycopeptides, and simultaneous analysis of both the carbohydrate and aglycan parts was carried out.