N‐METHYL PEPTIDES: III. Solution Conformational Study and Crystal Structure of N>‐Pivaloyl‐L‐Prolyl‐N‐Methyl‐N‘‐Isopropyl‐L‐Alaninamide*
- 1 April 1981
- journal article
- research article
- Published by Wiley in International Journal of Peptide and Protein Research
- Vol. 17 (4), 469-479
- https://doi.org/10.1111/j.1399-3011.1981.tb02016.x
Abstract
The study of tBuCO-l-Pro-Me-l-Ala-NHiPr (1) by i.r. and n.m.r. spectroscopies has indicated that the middle amide group accommodates preferentially the cis arrangement in inert (CCl4) and aprotic (DMSO) solvents. Cis conformers are folded by a strong intramolecular hydrogen bond involving both terminal CO and NH groups whereas the minor trans conformers accommodate an open conformation. The cis folded form is retained in the solid state and its crystal structure was fully characterized by X-ray diffraction.Keywords
This publication has 13 references indexed in Scilit:
- Structures of L-prolylsarcosine monohydrate and tert-butoxycarbonyl-L-prolylsarcosine benzyl esterActa crystallographica Section B, Structural science, crystal engineering and materials, 1980
- Experimental investigations on the backbone folding of proline‐containing model tripeptidesBiopolymers, 1979
- β-turns in proteinsJournal of Molecular Biology, 1977
- Conformations moléculaires à l'état solide des deux diastéréoisomères de la N-isobutyrylprolylalanine-isopropylamide. Comparaison avec les conformations adoptées en solutionActa Crystallographica Section B: Structural Science, Crystal Engineering and Materials, 1977
- N-Methylamino acids in peptide synthesis. V. The synthesis of N-tert-butyloxycarbonyl, N-methylamino acids by N-methylationCanadian Journal of Chemistry, 1977
- cis-Proline in the linear oligopeptide: structure of benzyloxycarbonyl-glycyl-prolyl-leucineActa crystallographica Section B, Structural science, crystal engineering and materials, 1976
- An X-ray study of ilamycin B1, a cyclic heptapeptide antibioticActa Crystallographica Section B: Structural Science, Crystal Engineering and Materials, 1974
- Chain reversals in proteinsBiochimica et Biophysica Acta (BBA) - Protein Structure, 1973
- STUDIES ON THE CONFORMATION OF AMINO ACIDSInternational Journal of Protein Research, 1971
- The application of phase relationships to complex structures. III. The optimum use of phase relationshipsActa Crystallographica Section A, 1971