Chakraborty, Tushar K. ; Ghosh, Animesh ; Kiran Kumar, S. ; Kunwar, Ajit C. (2003) Nucleation of β-hairpin structures with cis amide bonds in E-Vinylogous proline-containing peptides Journal of Organic Chemistry, 68 (16). pp. 6459-6462. ISSN 0022-3263
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Official URL: http://pubs.acs.org/doi/pdf/10.1021/jo034361j
Related URL: http://dx.doi.org/10.1021/jo034361j
Abstract
Synthesis and conformational studies of peptides containing the E-vinylogous prolines 1 (VPro1) and 2 (VPro2), Boc-Ala-Val-VPro1-Xaa-Leu-OMe (3, Xaa = Gly; 4, Xaa = Phe), Boc-Ala-Val-VPro2-Xaa-Leu-OMe (5, Xaa = Gly; 6, Xaa = Phe), Boc-Leu-Ile-Val-VPro1-Xaa-Leu-OMe (7, Xaa = Gly; 8, Xaa = Phe), and Boc-Leu-Ile-Val-VPro2-Xaa-Leu-OMe (9, Xaa = Gly; 10, Xaa = Phe), were carried out. It has been shown that both VPro1 and VPro2 lead to the formation of 12-membered intramolecularly hydrogen bonded structures very similar to type VI β-turns with a cis Xaa-VPro amide bond in the major conformers in all the peptides 3-10, resulting in the nucleation of β-hairpin type structures in these molecules in CDCl3.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to American Chemical Society. |
| ID Code: | 78258 |
| Deposited On: | 18 Jan 2012 12:14 |
| Last Modified: | 18 Jan 2012 12:14 |
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