Helix-Forming Carbohydrate Amino Acids

Claridge, Timothy D.W. and Long, Daniel D. and Baker, Christopher M. and Odell, Barbara and Grant, Guy H. and Edwards, Alison A. and Tranter, George E. and Fleet, George W.J. and Smith, Martin D. (2004) Helix-Forming Carbohydrate Amino Acids. Journal of Organic Chemistry, 70 (6). pp. 2082-2090. ISSN 0022-3263. (Access to this publication is restricted)

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Abstract

The solution-phase conformational properties of tetrameric and octameric chains of C-glycosyl alpha-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 pi-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.

Item Type: Article
Subjects: Q Science
Q Science > QD Chemistry
Divisions: Faculties > Science Technology and Medical Studies > Medway School of Pharmacy
Depositing User: Alison Edwards
Date Deposited: 08 Sep 2008 15:00
Last Modified: 05 Sep 2011 23:40
Resource URI: http://kar.kent.ac.uk/id/eprint/4890 (The current URI for this page, for reference purposes)
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