Determination of Absolute Stereochemistry of Natural Alicyclic Glycosides by 1H NMR Spectroscopy without Application of Chiral Reagents – An Indication
| Autor: | Natalya V. Ivanchina, V. A. Denisenko, Alla G. Guzii, Larisa K. Shubina, Tatyana N. Makarieva, Shamil Sh. Afiyatullov, Anatoly I. Kalinovsky, Valentin A. Stonik, Pavel S. Dmitrenok |
|---|---|
| Rok vydání: | 2011 |
| Předmět: |
Pharmacology
chemistry.chemical_classification Chemistry Stereochemistry Absolute configuration Glycoside Plant Science General Medicine Nuclear magnetic resonance spectroscopy chemistry.chemical_compound Alicyclic compound Aglycone Complementary and alternative medicine Drug Discovery Side chain Proton NMR Moiety |
| Zdroj: | Natural Product Communications. 6:1934578X1100600 |
| ISSN: | 1555-9475 1934-578X |
| DOI: | 10.1177/1934578x1100600520 |
| Popis: | A study has been made of the 1H NMR spectra of peracetylated β-glucopyranosides and α-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. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|