TY - JOUR
T1 - Design, Synthesis, and Antifungal Activity of 16,17-Dihydroheronamide C and ent-Heronamide C
AU - Kanoh, Naoki
AU - Terashima, Ryusei
AU - Nishiyama, Hiromichi
AU - Terajima, Yuta
AU - Nagasawa, Shota
AU - Sasano, Yusuke
AU - Iwabuchi, Yoshiharu
AU - Saito, Hiroaki
AU - Egoshi, Syusuke
AU - Dodo, Kosuke
AU - Sodeoka, Mikiko
AU - Pan, Chengqian
AU - Ikeuchi, Yoshinobu
AU - Nishimura, Shinichi
AU - Kakeya, Hideaki
N1 - Funding Information:
We thank Prof. Kaoru Takegawa (Kyushu University) for yeast strains. This work was supported in part by grants-in-Aid for Scientific Research on Innovative Areas from the Ministry of Education, Culture, Sports, Science and Technology, Japan (no. 17H06401 to H.K.; no. 20H04791 to H.S.; and no. 18H04603 to N.K.), a grant-in-Aid for Scientific Research (C) from the Japan Society for the Promotion of Science (no. 19K06990 to N.K. and no. 19K05378 to H.S.), and a grant from the Tokyo Biochemical Research Foundation to N.K. The MD computations in this study were performed using the Advanced Center for Computing and Communication of RIKEN, the Research Center for Computational Science of the Institute for Molecular Science (IMS), and the Research Center for Advanced Computing Infrastructure of the Japan Advanced Institute of Science and Technology (JAIST).
Publisher Copyright:
© 2021 American Chemical Society.
PY - 2021/12/3
Y1 - 2021/12/3
N2 - 16,17-Dihydroheronamide C (8) and ent-heronamide C (ent-1) were designed as probes for the mode-of-action analysis of heronamide C (1). These molecules were synthesized by utilizing a highly modular strategy developed in the preceding paper. The evaluation of the antifungal activity of these compounds revealed the exceptional importance of the C16-C17 double bond for the antifungal activity of heronamide C and the existence of chiral recognition between heronamide C (1) and cell membrane components.
AB - 16,17-Dihydroheronamide C (8) and ent-heronamide C (ent-1) were designed as probes for the mode-of-action analysis of heronamide C (1). These molecules were synthesized by utilizing a highly modular strategy developed in the preceding paper. The evaluation of the antifungal activity of these compounds revealed the exceptional importance of the C16-C17 double bond for the antifungal activity of heronamide C and the existence of chiral recognition between heronamide C (1) and cell membrane components.
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U2 - 10.1021/acs.joc.1c01761
DO - 10.1021/acs.joc.1c01761
M3 - Article
AN - SCOPUS:85120084884
SN - 0022-3263
VL - 86
SP - 16249
EP - 16258
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 23
ER -