An octameric carbopeptoid; secondary structure in octameric and tetrameric 5-aminomethyl-tetrahydrofuran-2-carboxylates

Tetrahedron Letters

Volumn 40, Issue 11, 1999, Pages 2199-2202

  Claridge, Timothy D W ^a   Long, Daniel D ^a   Hungerford, Natasha L ^a   Aplin, Robin T ^a   Smith, Martin D ^a   Marquess, Daniel G ^b,c   Fleet, George W J ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

^c Advanced Medicine Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID ETHYL ESTER; CARBOHYDRATE; HEXANE; OLIGOMER; PEPTIDE DERIVATIVE; TETRAHYDROFURAN DERIVATIVE; TETRAMER;

ALPHA HELIX; ARTICLE; CHROMATOGRAPHY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OLIGOMERIZATION; PROTEIN CONFORMATION; PROTEIN PURIFICATION; PROTEIN SECONDARY STRUCTURE; SYNTHESIS;

EID: 0033548539     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00111-2     Document Type: Article

References (11)

1. Long, D. D., Hungerford, N. L., Smith, M. D., Brittain, D. E. A., Marquess, D. G., Claridge, T. D. W., Fleet, G. W. J., Tetrahedron Lett., 1999, 40, 2195.
2. All spectra were recorded at 298K on a Bruker AMX500 spectrometer equipped with a inverse broadband z-gradient probe. TOCSY spectra were collected with an MLEV-17 spin-lock and a mixing time of 70 ms. ROESY spectra were collected with either a 200 ms CW spin-lock or a phase-alternating spin-lock to suppress TOCSY contributions (T-ROESY).
3. Willker, W., Leibfritz, D., Kerrsebaum, R., Bermel, W., Magn. Reson. Chem. 1993, 31, 287.
4. Hwang, T. L., Shaka, A. J., J. Magn. Reson. (B) 1993, 102, 155.
5. Each sugar residue of a carbopeptoid is labelled alphabetically from the N- to the C- terminus. Protons on each sugar ring are numbered according to IUPAC recommendations on carbohydrate nomenclature.
6. Smith, M. D., Claridge, T. D. W., Tranter, G. E., Sansom, M. S. P., Fleet, G. W. J., J. Chem. Soc., Chem. Commun., 1998, 2041; Long, D. D., Smith, M. D., Marquess, D. G., Claridge, T. D. W., Fleet, G. W. J., Tetrahedron Lett., 1998, 39, 9293.
7. Smith, M. D., Claridge, T. D. W., Tranter, G. E., Sansom, M. S. P., Fleet, G. W. J., J. Chem. Soc., Chem. Commun., 1998, 2041; Long, D. D., Smith, M. D., Marquess, D. G., Claridge, T. D. W., Fleet, G. W. J., Tetrahedron Lett., 1998, 39, 9293.
8. Kessler, H., Schmeider, P., Köck, M., Kurz, M. ,J. Magn. Reson. 1990, 88, 615.
9. Smith, M. D., Long, D. D., Martin, A., Marquess, D. G., Claridge, T. D. W., Fleet, G. W. J., Tetrahedron Lett. 1999, 40, 2191.
10. Gellmann, S. H., Acc. Chem. Res., 1998, 31, 173.
11. Support from the EPSRC and GlaxoWellcome is gratefully acknowledged.