Issue 7, 2011
From the journal:

MedChemComm

Structure–activity relationships of gramicidin S analogs containing (β-3-pyridyl)-α,β-dehydroalanine residues on membrane permeability†

Keiichi Yamada,*a   Makoto Kodaira,a   Shun-suke Shinoda,a   Keiko Komagoe,b   Hiroyuki Oku,a   Ryoichi Katakai,a   Takashi Katsub  and  Ichiro Matsuoa  

* Corresponding authors

a Department of Chemistry and Chemical Biology, Gunma University, 1-5-1, Tenjin-cho, Kiryu, Gunma, Japan
E-mail: kyamada@gunma-u.ac.jp
Fax: +81-277-30-1345
Tel: +81-277-30-1345

b Graduate School of Medicine, Dentistry and Pharmaceutical Sciences, Okayama University, 1-1-1, Tsushima-naka, Kita, Okayama, Japan

Abstract

The synthesis, biological activities and membrane permeability of gramicidin S (GS) analogs containing (Z)-(β-3-pyridyl)-α,β-dehydroalanine (ΔZ3Pal) residues are described. The cationic side chains of the Orn and ΔZ3Pal4,4′ residues in [ΔZ3Pal4,4′]GS (1) are important for dissociating antimicrobial and hemolytic activity.

Graphical abstract: Structure–activity relationships of gramicidin S analogs containing (β-3-pyridyl)-α,β-dehydroalanine residues on membrane permeability

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Article information

DOI
https://doi.org/10.1039/C1MD00081K
Article type
Concise Article
Submitted
22 Mar 2011
Accepted
18 Apr 2011
First published
19 May 2011

Med. Chem. Commun., 2011,2, 644-649

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Structure–activity relationships of gramicidin S analogs containing (β-3-pyridyl)-α,β-dehydroalanine residues on membrane permeability

K. Yamada, M. Kodaira, S. Shinoda, K. Komagoe, H. Oku, R. Katakai, T. Katsu and I. Matsuo, Med. Chem. Commun., 2011, 2, 644 DOI: 10.1039/C1MD00081K

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