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  Enhanced beta-turn conformational stability of tripeptides containing Delta Phe in cis over trans configuration.

Jaremko, M., Jaremko, L., Mazur, A., Makowski, M., & Lisowski, M. (2013). Enhanced beta-turn conformational stability of tripeptides containing Delta Phe in cis over trans configuration. Amino Acids, 45(4), 865-875. doi:10.1007/s00726-013-1534-9.

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Item Permalink: http://hdl.handle.net/11858/00-001M-0000-0014-6A35-1 Version Permalink: http://hdl.handle.net/11858/00-001M-0000-0027-CB62-1
Genre: Journal Article

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Jaremko, M.1, Author              
Jaremko, L.1, Author              
Mazur, A.1, Author              
Makowski, M., Author
Lisowski, M., Author
Affiliations:
1Department of NMR Based Structural Biology, MPI for Biophysical Chemistry, Max Planck Society, ou_578567              

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Free keywords: Dehydropeptides; Dehydrophenylalanine configuration; Circular dichroism; Nuclear magnetic resonance; Dehydropeptide conformation; Temperature coefficients of amide protons
 Abstract: Conformations of three pairs of dehydropeptides with the opposite configuration of the Delta Phe residue, Boc-Gly-Delta(Z/E)Phe-Phe-p-NA (Z- p -NA and E- p -NA), Boc-Gly-Delta(Z/E)Phe-Phe-OMe (Z-OMe and E-OMe), and Boc-Gly-Delta(Z/E)Phe-Phe-OH (Z-OH and E-OH) were compared on the basis of CD and NMR studies in MeOH, TFE, and DMSO. The CD results were used as the additional input data for the NMR-based calculations of the detailed solution conformations of the peptides. It was found that Z- p -NA, E- p -NA, Z-OMe, and Z-OH adopt the beta-turn conformations and E-OMe and E-OH are unordered. There are two overlapping type III beta-turns in Z- p -NA, type II' beta-turn in E- p -NA, and type II beta-turn in Z-OMe and Z-OH. The results obtained indicate that in the case of methyl esters and peptides with a free carboxyl group, Delta(Z)Phe is a much stronger inducer of ordered conformations than Delta(E)Phe. It was also found that temperature coefficients of the amide protons are not reliable indicators of intramolecular hydrogen bonds donors in small peptides.

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Language(s): eng - English
 Dates: 2013-10
 Publication Status: Published in print
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 Rev. Method: Peer
 Identifiers: DOI: 10.1007/s00726-013-1534-9
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Title: Amino Acids
Source Genre: Journal
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Pages: - Volume / Issue: 45 (4) Sequence Number: - Start / End Page: 865 - 875 Identifier: ISSN: 0939-4451