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. 2024;72(9):826-830.
doi: 10.1248/cpb.c24-00533.

Synthesis and Cytotoxicity of Cyclic Octapeptide Surugamides with Varied N-Acyl Moieties

Kenichi Matsuda  1 , Shinya Niikura  1 , Rintaro Ichihara  1 , Kei Fujita  1 , Anna M Strasser  1 , Rokusuke Yoshikawa  2   3 , Jiro Yasuda  2   3   4 , Yoshiki Hiramatsu  5 , Hironori Hayashi  5   6 , Eiichi N Kodama  5   6   7 , Toshiyuki Wakimoto  1
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Free article

Synthesis and Cytotoxicity of Cyclic Octapeptide Surugamides with Varied N-Acyl Moieties

Kenichi Matsuda et al. Chem Pharm Bull (Tokyo). 2024.
Free article

Abstract

Surugamides are a group of non-ribosomal peptides produced by Streptomyces spp. Several derivatives possess acyl groups, which are proposed to be attached to a lysine side chain after backbone-macrocyclization during biosynthesis. To date, five different acyl groups have been identified in nature, yet their impacts on biological activity remain underexplored. Here we synthesized surugamide B derivatives with varied acyl moieties. Biological evaluations revealed that larger hydrophobic acyl groups on lysine ε-NH2 enhance cytotoxicity.

Keywords: acylation; cyclic peptide; non-ribosomal peptide.

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