Vibrational circular dichroism of monosaccharides

Vibrational absorption and circular dichroism spectra of several monosaccharides in the 1500-1180 cm(-1) region are presented. The spectra are analyzed for similarities and differences among anomeric, homomorphic and epimeric pairs of sugars. Among the anomeric sugars, distinct bands characteristic of anomers are present that can be used to characterize the anomers. The homomorphic sugars are found to give rise to similar vibrational circular dichroism (VCD) sign patterns provided that the substituents do not have interfering VCD bands, or those interfering bands can be identified and properly accounted far. The epimeric sugars have markedly different VCD spectra, indicating that VCD is sensitive to the chirality at individual chiral centers. (C) 1999 Elsevier Science Ltd. All rights reserved.