Issue 77, 2016

Re-evaluation of the N-terminal substitution and the D-residues of teixobactin

Abstract

Teixobactin is a head to side-chain cyclic depsipeptide with a guanidino based residue within the cycle, three D-amino acids in the tail, and a N-methylated terminal residue. The synthesis of the first analogue, containing Arg, was recently described by our group. Herein, we demonstrated that analogues of Arg. Teixobactin bearing either (a) three L-amino acids in the tail and keeping the N-methyl at the N-terminal or (b) with three D-amino acids, but with acetylation of the N-terminal, are inactive against Gram(+) and Gram(−) bacteria. These results complement those published by the groups of Madder, Taylor, and Singh that have shown that both modifications: L-amino acids and N-acetylation also led to loss of biological activity.

Graphical abstract: Re-evaluation of the N-terminal substitution and the D-residues of teixobactin

Supplementary files

Article information

Article type
Communication
Submitted
11 iyl 2016
Accepted
28 iyl 2016
First published
28 iyl 2016

RSC Adv., 2016,6, 73827-73829

Re-evaluation of the N-terminal substitution and the D-residues of teixobactin

S. A. H. Abdel Monaim, Y. E. Jad, G. A. Acosta, T. Naicker, E. J. Ramchuran, A. El-Faham, T. Govender, H. G. Kruger, B. G. de la Torre and F. Albericio, RSC Adv., 2016, 6, 73827 DOI: 10.1039/C6RA17720D

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