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Updated: Oct 26, 2026

An Efficient Method for the Synthesis of Peptoids with Mixed Lysine-type/Arginine-type Monomers and Evaluation of Their Anti-leishmanial Activity
Published on: November 2, 2016
Tonakiamides A and B, Antitrypanosomal Lipopeptides Isolated from a Marine Okeania sp. Cyanobacterium
Natsumi Watanabe1, Ghulam Jeelani2, Tomoyoshi Nozaki2
1Department of Applied Chemistry, Chuo University, 1-13-27 Kasuga, Bunkyo-ku, Tokyo112-8551, Japan.
Abstract:
The structure elucidation of peptidic natural products is often hindered by extensive N-methylation and repetitive sequence motifs, which complicate NMR spectral analysis. Tonakiamides A and B (1 and 2), two lipopeptides isolated from a marine Okeania sp. cyanobacterium collected in Japan, represent such challenging compounds. Tonakiamides A and B (1 and 2) are acyclic nonapeptides composed of a hexanoic acid moiety and nine amino acid residues, six of which are N-methylated, resulting in complex mixtures of rotamers. Their structures were elucidated through a combination of spectroscopic and spectrometric analyses together with the characterization of three partial hydrolysates obtained under mild hydrolysis conditions. Tonakiamides A and B exhibited moderate growth-inhibitory activities against Trypanosoma brucei rhodesiense, the causative agent of African sleeping sickness.
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