Literature DB >> 27833030

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

Alexey G Gerbst1, Vadim B Krylov1, Dmitry A Argunov1, Arsenii S Solovev1, Andrey S Dmitrenok1, Alexander S Shashkov1, Nikolay E Nifantiev2.   

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 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. Copyright Â
© 2016 Elsevier Ltd. All rights reserved.

Entities:  

Keywords:  Conformation analysis; O-sulfation; Pyranoside; ab initio calculations

Mesh:

Substances:

Year:  2016        PMID: 27833030     DOI: 10.1016/j.carres.2016.10.011

Source DB:  PubMed          Journal:  Carbohydr Res        ISSN: 0008-6215            Impact factor:   2.104


  2 in total

1.  Influence of per-O-sulfation upon the conformational behaviour of common furanosides.

Authors:  Alexey G Gerbst; Vadim B Krylov; Dmitry A Argunov; Maksim I Petruk; Arsenii S Solovev; Andrey S Dmitrenok; Nikolay E Nifantiev
Journal:  Beilstein J Org Chem       Date:  2019-03-15       Impact factor: 2.883

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Authors:  Mohit Chhabra; Jennifer C Wilson; Liang Wu; Gideon J Davies; Neha S Gandhi; Vito Ferro
Journal:  Chemistry       Date:  2022-01-31       Impact factor: 5.020

  2 in total

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