Helix-Forming Carbohydrate Amino Acids

Claridge, Timothy D.W., Long, Daniel D., Baker, Christopher M., Odell, Barbara, Grant, Guy H., Edwards, Alison A., Tranter, George E., Fleet, George W.J., Smith, Martin D. (2004) Helix-Forming Carbohydrate Amino Acids. Journal of Organic Chemistry, 70 (6). pp. 2082-2090. ISSN 0022-3263. (doi:10.1021/jo0480040) (Access to this publication is currently restricted. You may be able to access a copy if URLs are provided) (KAR id:4890)

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Official URL: https://doi.org/10.1021/jo0480040

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
DOI/Identification number:	10.1021/jo0480040
Subjects:	Q Science Q Science > QD Chemistry
Divisions:	Divisions > Division of Natural Sciences > Medway School of Pharmacy
Depositing User:	Alison Edwards
Date Deposited:	08 Sep 2008 15:00 UTC
Last Modified:	05 Nov 2024 09:36 UTC
Resource URI:	https://kar.kent.ac.uk/id/eprint/4890 (The current URI for this page, for reference purposes)

University of Kent Author Information

Edwards, Alison A..

Creator's ORCID:	https://orcid.org/0000-0002-4637-9373
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