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Helix-forming carbohydrate amino acids

  • Lee Smith
    ,
  • Guy Grant
    ,
  • Timothy D.W. Claridge
    ,
  • Daniel D. Long
    ,
  • Christopher M. Baker
    ,
  • Barbara Odell
  • University of Oxford
    ,
  • Imperial College London
    ,
  • University of Cambridge
Research Output: Contribution to journal Article Peer-review

Abstract

The solution-phase conformational properties of tetrameric and octameric chains of C-glycosyl α-d-lyxofuranose configured tetrahydrofuran amino acids (where the C-2 and C-5 substituents on the tetrahydrofuran ring are trans to each other) were examined using NMR and IR and CD in organic solvents. Studies by NMR and IR demonstrated that in chloroform solution, the tetramer 7 does not adopt a hydrogen-bonded conformation whereas the octamer 10 populates a well-defined helical secondary structure stabilized by 16-membered (i, i − 3) interresidue hydrogen bonds, similar to a π-helix. Circular dichroism studies in trifluoroethanol are consistent with this conformation for the octamer 10, and also indicate that the tetramer 7 adopts a rigid conformation not stabilized by hydrogen bonds.

Publication Information

Output type

Research Output: Contribution to journal Article Peer-review

Original language

English

Pages from-to (Number of pages)

Pages 2082-2090

Journal (Volume, Issue Number)

Journal of Organic Chemistry (Volume 70, Issue 6)

Publication milestones

  • Published - 01/01/2005

Publication status

Published - 01/01/2005

ISSN

0022-3263

External Publication IDs

  • handle.net: 10547/294638
  • Scopus: 15444372596

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