title: Determination of absolute stereochemistry of natural alicyclic glycosides by 1H NMR spectroscopy without application of chiral reagents--an indication.
abstract: A study has been made of the 1H NMR spectra of peracetylated beta-glucopyranosides and alpha-arabinopyranosides obtained by reaction of D- and L-glucoses, and L- and D-arabinoses with either (R)- or (S)-2-octanols. The obtained and literature data show that 1H NMR spectra may be used to determine the absolute configuration of the aglycone moieties of some alicyclic glycosides without the need to synthesize derivatives with chiral reagents, as long as the absolute configuration of their monosaccharide moiety is known or vice versa. Spectra of marine steroid glycosides and their acetates containing glycosylated side chains as alicyclic fragments were also examined. It was shown that analysis of 1H NMR spectra for the determination of the absolute configuration is more applicable in the cases when glycosides have the same substitution in the D-ring of the aglycone moiety.
authors: Pacific Institute ofBioorganic Chemistry, FEB RAS, pr. 100 let Vladivostoku, 159, Vladivostok 690022, Russian Federation.
authors: Tatyana N
authors: TN
authors: Makarieva
authors: Larisa K
authors: LK
authors: Shubina
authors: Alla G
authors: AG
authors: Guzii
authors: Natalya V
authors: NV
authors: Ivanchina
authors: Vladimir A
authors: VA
authors: Denisenko
authors: Shamil S
authors: SS
authors: Afiyatullov
authors: Pavel S
authors: PS
authors: Dmitrenok
authors: Anatoly I
authors: AI
authors: Kalinovsky
authors: Valentin A
authors: VA
authors: Stonik