Stereochemical analysis of d-glucopyranosyl-sulfoxides via a combined NMR,molecular modeling and X-ray crystallographic approach |
| |
| Institution: | 1. Laboratório de Química de Plantas Medicinais, Instituto de Pesquisas de Produtos Naturais, Centro de Ciências da Saúde, Universidade Federal do Rio de Janeiro, P.O. Box 68045, CEP 21941-971 Rio de Janeiro, Brazil;2. Laboratório Multiusuário de Análises por Ressonância Magnética Nuclear, Instituto de Pesquisas de Produtos Naturais, Centro de Ciências da Saúde, Universidade Federal do Rio de Janeiro, CEP 21941-902 Rio de Janeiro, Brazil;1. Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, 266003 Qingdao, PR China;2. Department of Pharmacognosy, Faculty of Pharmacy, University of Lagos, Nigeria;3. Institut für Pharmazeutische Biologie und Biotechnologie, Heinrich-Heine-Universität Düsseldorf, 40225 Düsseldorf, Germany |
| |
| Abstract: | (S)-α-Methoxyphenylacetic acid (MPAA) was used as an NMR shift reagent in combination with molecular modeling to predict the absolute configuration of a representative epimeric pair of glucopyranosyl sulfoxides. The correctness of this assignment was confirmed by X-ray crystallographic examination of one of the epimers, 3a1. The crystal structure of ethyl 2,3-di-O-acetyl-4,6-O-benzylidene-1-thio-β-d-glucopyranoside S-oxide monohydrate 3a1 was solved by direct methods and was shown to bear the (R)-configuration at the sulfinyl center in accordance with our prediction. Furthermore, the conformation of 3a1 in the solid state was found to be remarkably similar to that predicted by molecular mechanics calculations. |
| |
| Keywords: | |
| 本文献已被 ScienceDirect 等数据库收录！ |
|
