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Trisubstituted (E)-alkene dipeptide isosteres as β-turn promoters in the gramicidin S cyclodecapeptide scaffold

Xiao, J and Weisblum, B and Wipf, P (2006) Trisubstituted (E)-alkene dipeptide isosteres as β-turn promoters in the gramicidin S cyclodecapeptide scaffold. Organic Letters, 8 (21). 4731 - 4734. ISSN 1523-7060

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Abstract

(Chemical Equation Presented) A concise synthesis of a gramicidin S analogue with trisubstituted (E)-alkene dipeptide isostere (TEADI) replacements at both D-Phe-Pro positions was realized. Conformational analysis demonstrated that TEADIs can serve as type II β-turn promoters in a cyclic scaffold and successfully mimic a proline residue. © 2006 American Chemical Society.

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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Xiao, J
Weisblum, B
Wipf, Ppwipf@pitt.eduPWIPF
Date: 12 October 2006
Date Type: Publication
Journal or Publication Title: Organic Letters
Volume: 8
Number: 21
Page Range: 4731 - 4734
DOI or Unique Handle: 10.1021/ol0617704
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 1523-7060
MeSH Headings: Alkenes--chemistry; Dipeptides--chemistry; Gramicidin--chemical synthesis; Gramicidin--chemistry; Molecular Mimicry; Molecular Structure; Peptides, Cyclic--chemical synthesis; Peptides, Cyclic--chemistry; Proline--chemistry; Protein Conformation; Protein Structure, Secondary
Other ID: NLM NIHMS61354, NLM PMC2631548
PubMed Central ID: PMC2631548
PubMed ID: 17020289
Date Deposited: 28 Oct 2013 20:53
Last Modified: 02 Feb 2019 15:56
URI: http://d-scholarship-dev.library.pitt.edu/id/eprint/19896

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