Ring distortion in pyranosides caused by per-O-sulfation.
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 between3,OB and3S1was found, while complete4C1→1C4inversion was detected in xylopyranoside. The conformational changes were evidenced experimentally by measuring intra-ring1H-1H coupling constants and nuclear Overhauser effect (NOE) and were additionally confirmed by ab initio calculations.
Laboratory of Glycoconjugate Chemistry, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, 119991 Moscow, Russian Federation.
Alexey G
AG
Gerbst
Laboratory of Glycoconjugate Chemistry, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, 119991 Moscow, Russian Federation.
Vadim B
VB
Krylov
Laboratory of Glycoconjugate Chemistry, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, 119991 Moscow, Russian Federation.
Dmitry A
DA
Argunov
Laboratory of Glycoconjugate Chemistry, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, 119991 Moscow, Russian Federation.
Arsenii S
AS
Solovev
Laboratory of Glycoconjugate Chemistry, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, 119991 Moscow, Russian Federation.
Andrey S
AS
Dmitrenok
Laboratory of Glycoconjugate Chemistry, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, 119991 Moscow, Russian Federation.
Alexander S
AS
Shashkov
Laboratory of Glycoconjugate Chemistry, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, 119991 Moscow, Russian Federation. Electronic address: nen@ioc.ac.ru.
Nikolay E
NE
Nifantiev
D002236:Carbohydrate Conformation; D005960:Glucosides / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D013431:Sulfates / Q000378:metabolism
D005960:Glucosides; D013431:Sulfates
Conformation analysis; O-sulfation; Pyranoside; ab initio calculations