2.50
Hdl Handle:
http://hdl.handle.net/10547/294638
Title:
Helix-forming carbohydrate amino acids
Authors:
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.
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.
Citation:
Claridge, T.D.W., Long, D.D., Baker, C.M., Odell, B., Grant, G.H., Edwards, A.A., Tranter, G.E., Fleet, G.W.J., Smith, M.D. (2005) 'Helix-Forming carbohydrate amino acids', Journal of Organic Chemistry, 70(6), pp.2082-2090.
Publisher:
American Chemical Society
Journal:
The Journal of Organic Chemistry
Issue Date:
2005
URI:
http://hdl.handle.net/10547/294638
DOI:
10.1021/jo0480040
Additional Links:
http://pubs.acs.org/doi/abs/10.1021/jo0480040
Type:
Article
Language:
en
ISSN:
0022-3263; 1520-6904
Appears in Collections:
Cell and Cryobiology Research Group

Full metadata record

DC FieldValue Language
dc.contributor.authorClaridge, Timothy D.W.en_GB
dc.contributor.authorLong, Daniel D.en_GB
dc.contributor.authorBaker, Christopher M.en_GB
dc.contributor.authorOdell, Barbaraen_GB
dc.contributor.authorGrant, Guy H.en_GB
dc.contributor.authorEdwards, Alison A.en_GB
dc.contributor.authorTranter, George E.en_GB
dc.contributor.authorFleet, George W.J.en_GB
dc.contributor.authorSmith, Martin D.en_GB
dc.date.accessioned2013-06-26T14:45:59Z-
dc.date.available2013-06-26T14:45:59Z-
dc.date.issued2005-
dc.identifier.citationClaridge, T.D.W., Long, D.D., Baker, C.M., Odell, B., Grant, G.H., Edwards, A.A., Tranter, G.E., Fleet, G.W.J., Smith, M.D. (2005) 'Helix-Forming carbohydrate amino acids', Journal of Organic Chemistry, 70(6), pp.2082-2090.en_GB
dc.identifier.issn0022-3263-
dc.identifier.issn1520-6904-
dc.identifier.doi10.1021/jo0480040-
dc.identifier.urihttp://hdl.handle.net/10547/294638-
dc.description.abstractThe 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.en_GB
dc.language.isoenen
dc.publisherAmerican Chemical Societyen_GB
dc.relation.urlhttp://pubs.acs.org/doi/abs/10.1021/jo0480040en_GB
dc.rightsArchived with thanks to The Journal of Organic Chemistryen_GB
dc.titleHelix-forming carbohydrate amino acidsen
dc.typeArticleen
dc.identifier.journalThe Journal of Organic Chemistryen_GB
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