Ring distortion in pyranosides caused by per-O-sulfation.

Alexey G Gerbst, Vadim B Krylov, Dmitry A Argunov, Arsenii S Solovev, Andrey S Dmitrenok, Alexander S Shashkov, Nikolay E Nifantiev

Journal: Carbohydrate research 2017;436():20-24

PMID: 27833030

Full Text on Elsevier Science View on PubMed

Abstract

Distortion of the ring conformation in β-gluco- and β-xylopyranosides upon their per-O-sulfation was observed. In the case of glucose, a conformation intermediate between B and S was found, while complete C→C inversion was detected in xylopyranoside. The conformational changes were evidenced experimentally by measuring intra-ring H-H coupling constants and nuclear Overhauser effect (NOE) and were additionally confirmed by ab initio calculations.

Address: Laboratory of Glycoconjugate Chemistry, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, 119991 Moscow, Russian Federation.; Laboratory of Glycoconjugate Chemistry, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, 119991 Moscow, Russian Federation. Electronic address: [email protected].

DOI: 10.1016/j.carres.2016.10.011

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MeSH Terms: Carbohydrate Conformation, Glucosides, Magnetic Resonance Spectroscopy, Models, Molecular, Sulfates