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Paper | Regular issue | Vol 91, No. 11, 2015, pp.2143-2151
Published online, 28th October, 2015
DOI: 10.3987/COM-15-13325
Synthesis and Antibacterial Activity of Tripropeptin C Derivatives Containing the Pyrimidine Ring System

Sehei Hirosawa, Yoshiaki Takahashi,* Ayumi Murotani, Hideki Hashizume, Toshiaki Miyake, and Yuzuru Akamatsu

*Hiyoshi branch, Institute of Microbial Chemistry (BIKAKEN), 3-34-17, Ida Nakahara-ku, Kawasaki, Kanagawa 211-0035, Japan

Abstract

A series of modifications to the terminal guanidine group of the arginine residue in tripropeptin C was performed, and the corresponding pyrimidine derivatives were synthesized as a part of a structure-activity relationship study. Some of the resulting compounds maintained excellent antibacterial activity. Our findings indicated that the guanidine group in tripropeptin C is not essential for the antibacterial activity of this compound, and the possibility of chemical modification of the guanidine group was demonstrated.