Issue 8, 2010
From the journal:

Organic & Biomolecular Chemistry

Antimicrobially active cycloundecapeptides related to gramicidin S having a novel turn structure with cisd-Phe-Propeptide bond†

Makoto Tamaki,*a   Ichiro Sasaki,a   Manabu Kokuno,a   Mitsuno Shindo,b   Masahiro Kimurab  and  Yoshiki Uchidab  

* Corresponding authors

a Department of Chemistry, Toho University, Funabashi, Chiba, Japan
E-mail: tamaki@chem.sci.toho-u.ac.jp
Fax: +81-47-472-1855
Tel: +81-47-472-4323

b Department of Food Science and Nutrition, Osaka Shoin Women's University, Higashi-Osaka, Osaka, Japan
Fax: +81-6-6723-8348
Tel: +81-6-6723-8181(ext335)

Abstract

Antimicrobially active cycloundecapeptides related to gramicidin S, cyclo(-Val1-Orn2-Leu3-X4-D-Phe5-Pro6-Val7-Orn8- Leu9-D-Phe10-Pro11-) (X= Leu (1), Ala (2), Orn (3), Lys (4) and Arg (5)), were synthesized. From the CD and NMR studies, 1–5 possess antiparallel β-sheet conformation linked by a type II’β-turn around D-Phe10-Pro11 and a novel turn structure around X4-D-Phe5-Pro6 sequence with cisD-Phe-Pro peptide bond. The structural modifications at position 4 of 1–5 are beneficial to identification of novel antibiotic candidates without hemolytic activity.

Graphical abstract: Antimicrobially active cycloundecapeptides related to gramicidin S having a novel turn structure with cisd-Phe-Pro peptide bond

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Article information

DOI
https://doi.org/10.1039/B922159J
Article type
Paper
Submitted
23 Oct 2009
Accepted
25 Jan 2010
First published
15 Feb 2010

Org. Biomol. Chem., 2010,8, 1791-1797

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Antimicrobially active cycloundecapeptides related to gramicidin S having a novel turn structure with cisD-Phe-Pro peptide bond

M. Tamaki, I. Sasaki, M. Kokuno, M. Shindo, M. Kimura and Y. Uchida, Org. Biomol. Chem., 2010, 8, 1791 DOI: 10.1039/B922159J

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