Link to the University of Pittsburgh Homepage
Link to the University Library System Homepage Link to the Contact Us Form
D-Scholarship @ Pitt Banner and Links to Homepage

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

[img] Plain Text (licence)
Available under License : See the attached license file.
Download (1kB)

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.

Share

Citation/Export:
Social Networking:
Share |

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.pitt.edu/id/eprint/19896

Metrics

Monthly Views for the past 3 years

Plum Analytics

Altmetric.com

Actions (login required)

View Item View Item