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Sophie Manner

Director of studies

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Exploration of conformational flexibility and hydrogen bonding of xylosides in different solvents, as a model system for enzyme active site interactions

Author

  • Jerk Ronnols
  • Sophie Manner
  • Anna Siegbahn
  • Ulf Ellervik
  • Goran Widmalm

Summary, in English

The predominantly populated conformation of carbohydrates in solution does not necessarily represent the biologically active species; rather, any conformer accessible without too large an energy penalty may be present in a biological pathway. Thus, the conformational preferences of a naphthyl xyloside, which initiates in vivo synthesis of antiproliferative glycosaminoglycans, have been studied by using NMR spectroscopy in a variety of solvents. Equilibria comprising the conformations C-4(1), S-2(0) and C-1(4) were found, with a strong dependence on the hydrogen bonding ability of the solvent. Studies of fluorinated analogues revealed a direct hydrogen bond from the hydroxyl group at C2 to the fluorine atom at C4 by a (1h)J(F4,HO2) coupling. Hydrogen bond directionality was further established via comparisons of fluorinated levoglucosan molecules.

Department/s

  • Centre for Analysis and Synthesis

Publishing year

2013

Language

English

Pages

5465-5472

Publication/Series

Organic and Biomolecular Chemistry

Volume

11

Issue

33

Document type

Journal article

Publisher

Royal Society of Chemistry

Topic

  • Chemical Sciences

Status

Published

ISBN/ISSN/Other

  • ISSN: 1477-0539