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Sophie Manner

Studierektor

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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

Författare

  • 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.

Avdelning/ar

  • Centrum för analys och syntes

Publiceringsår

2013

Språk

Engelska

Sidor

5465-5472

Publikation/Tidskrift/Serie

Organic and Biomolecular Chemistry

Volym

11

Issue

33

Dokumenttyp

Artikel i tidskrift

Förlag

Royal Society of Chemistry

Ämne

  • Chemical Sciences

Status

Published

ISBN/ISSN/Övrigt

  • ISSN: 1477-0539