Intramolecular catalysis of the cis-trans isomerization of proline peptide bonds in cyclic disulfide-containing peptides [16]

Journal of the American Chemical Society

Volumn 122, Issue 10, 2000, Pages 2401-2402

  Rabenstein, Dallas L ^a   Shi, Tiesheng ^a   Spain, Stephen ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DISULFIDE; PEPTIDE; PROLINE;

CATALYSIS; CHEMICAL REACTION; CONFORMATIONAL TRANSITION; ENTHALPY; ISOMERISM; LETTER; PROTEIN BINDING; REACTION ANALYSIS; REACTION TIME;

EID: 0034653635     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja993901k     Document Type: Letter

References (23)

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11. 2) dipolar cross-peaks in ROESY spectra.
12. trans|) and t is a variable delay during which transfer of magnetization occurs by interchange between the cis and trans isomers. The inversion-transfer method used here is described in the following: Robinson. G.; Kuchel, P. W.; Chapman, B. E.; Doddrell, D. M.; Irving, M. G. J. Magn. Reson. 1985, 63, 314-319.
13. Rate constants were obtained from the inversion-transfer data by methods described in the following: Mariappan, S. V. S.; Rabenstein, D. L. J. Magn. Reson. 1992, 100, 13830-13837.
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15. 3
16. The structure of the trans isomer in Figure 2 is quite similar to crystal structures reported for the trans isomers of the disulfide forms of Ac-Cys-Pro-Ser-Cys-NHMe and Ac-Cys-Pro-Val-Cys-NHMe. Falconer, C. M.; Meinwald, Y. C.; Choudhary, I.; Talluri, S.; Milburn, P. J.; Clardy, J.; Scheraga, H. A. J. Am. Chem. Soc. 1992, 114, 4036-4042.
17. The molecular mechanics simulations show that 1b and 2b interconvert among an ensemble of random conformations.
18. The Monte Carlo molecular mechanics simulations were performed using Macromodel V6.5 and the OPLS force field. A 10 000 structure conformational search was performed, with each structure minimized by PRCG. The solvent for simulation was water.
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