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.
Issue Date
2005
Metadata
Show full item recordAbstract
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 SocietyJournal
The Journal of Organic ChemistryAdditional Links
http://pubs.acs.org/doi/abs/10.1021/jo0480040Type
ArticleLanguage
enISSN
0022-32631520-6904
ae974a485f413a2113503eed53cd6c53
10.1021/jo0480040