Steric effects on the amide isomer equilibrium of prolyl peptides. Synthesis and conformational analysis of N-acetyl-5-tert-butylproline N′-methylamides

Journal of the American Chemical Society

Volumn 118, Issue 51, 1996, Pages 12902-12908

  Beausoleil, Eric ^a   Lubell, William D ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; AMINO ACID DERIVATIVE; PROLINE DERIVATIVE;

ARTICLE; INFRARED SPECTROPHOTOMETRY; NUCLEAR MAGNETIC RESONANCE; PEPTIDE SYNTHESIS; PROTEIN STRUCTURE;

EID: 0030461902     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja962013b     Document Type: Article

References (62)

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13. Azabicycloalkane Gly-Pro type VI β-turn peptidomimetics are described: (a) Dumas, J.-P.; Germanas, J. P. Tetrahedron Lett. 1994, 35, 1493. (b) Gramberg, D.; Robinson, J. A. Tetrahedron Lett. 1994, 35, 861. (c) Kim, K.; Dumas, J.-P.; Germanas, J. P. J. Org. Chem. 1996, 61, 3138. (d) Gramberg, D.; Weber, C.; Beeli, R.; Inglis, J.; Bruns, C.; Robinson, J. A. Helv. Chim. Acta 1995, 78, 1588. Bicyclic X-Pro amide cis-isomer mimetics are also presented: (e) Curran, T. P.; McEnaney, P. M. Tetrahedron Lett. 1995, 36, 191. (f) Lenman, M. M.; Ingham, S. L.; Gani, D. Chem. Commun. 1996, 85.
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16. Azabicycloalkane Gly-Pro type VI β-turn peptidomimetics are described: (a) Dumas, J.-P.; Germanas, J. P. Tetrahedron Lett. 1994, 35, 1493. (b) Gramberg, D.; Robinson, J. A. Tetrahedron Lett. 1994, 35, 861. (c) Kim, K.; Dumas, J.-P.; Germanas, J. P. J. Org. Chem. 1996, 61, 3138. (d) Gramberg, D.; Weber, C.; Beeli, R.; Inglis, J.; Bruns, C.; Robinson, J. A. Helv. Chim. Acta 1995, 78, 1588. Bicyclic X-Pro amide cis-isomer mimetics are also presented: (e) Curran, T. P.; McEnaney, P. M. Tetrahedron Lett. 1995, 36, 191. (f) Lenman, M. M.; Ingham, S. L.; Gani, D. Chem. Commun. 1996, 85.
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47. The measured rates of magnetization transfer from trans to cis isomer for 1 were 0.1970 at 55 °C, 0.5030 at 60 °C and 1.0007 at 70 °C; for 3 the rates were 0.2368 at 65 °C, 0.5567 at 75 °C and 0.8626 at 85 °C. The values for the energy barriers and uncertainties were calculated as described: (a) Mariappan, S. V. S.; Rabenstein, D. L. J. Org. Chem. 1992, 57, 6675. (b) Freeman, R. A Handbook of Nuclear Magnetic Resonance; John Wiley & Sons, Inc.: New York, 1988; pp 198-202. (c) Perrin, C. L.; Thoburn, J. D.; Kresge. A. J. J. Am. Chem. Soc. 1992, 114, 8800.
48. The measured rates of magnetization transfer from trans to cis isomer for 1 were 0.1970 at 55 °C, 0.5030 at 60 °C and 1.0007 at 70 °C; for 3 the rates were 0.2368 at 65 °C, 0.5567 at 75 °C and 0.8626 at 85 °C. The values for the energy barriers and uncertainties were calculated as described: (a) Mariappan, S. V. S.; Rabenstein, D. L. J. Org. Chem. 1992, 57, 6675. (b) Freeman, R. A Handbook of Nuclear Magnetic Resonance; John Wiley & Sons, Inc.: New York, 1988; pp 198-202. (c) Perrin, C. L.; Thoburn, J. D.; Kresge. A. J. J. Am. Chem. Soc. 1992, 114, 8800.
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