Ring distortion in pyranosides caused by per-O-sulfation

Ring distortion in pyranosides caused by per-O-sulfation Full article

Journal

Carbohydrate Research
ISSN: 1873-426X , E-ISSN: 0008-6215

Output data

Year: 2016, Volume: 436, Pages: 20-24 Pages count : 5 DOI: 10.1016/j.carres.2016.10.011

Authors

Gerbst Alexey G. ¹ , Krylov Vadim B. ¹ , Argunov Dmitry A. ¹ , Solovev Arsenii S. ¹ , Dmitrenok Andrey S. ¹ , Shashkov Alexander S. ¹ , Nifantiev Nikolay E. ¹

Affiliations

1	Laboratory of Glycoconjugate Chemistry, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, 119991 Moscow, Russian Federation

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 3,OB and 3S1 was found, while complete 4C1→1C4 inversion was detected in xylopyranoside. The conformational changes were evidenced experimentally by measuring intra-ring 1H–1H coupling constants and nuclear Overhauser effect (NOE) and were additionally confirmed by ab initio calculations.

Gerbst A.G. , Krylov V.B. , Argunov D.A. , Solovev A.S. , Dmitrenok A.S. , Shashkov A.S. , Nifantiev N.E.
Ring distortion in pyranosides caused by per-O-sulfation
Carbohydrate Research. 2016. V.436. P.20-24. DOI: 10.1016/j.carres.2016.10.011 WOS Scopus OpenAlex

≡ Web of science:	WOS:000389516000003
≡ Scopus:	2-s2.0-84994311278
≡ OpenAlex:	W2539464588