Genome Mining-Based Discovery of Pyrano[2,3-c]pyrrole Type Natural Products Possessing Alkyl Side Chain with Branched Methyl Groups
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Ozaki, Taro
Morishita, Yohei
Taniguchi, Tohru
Sato, Hiroyasu
Aoyama, Yoshitaka
Sugawara, Akihiro
Numata, Kaho
Fuse, Tomoya
Matsuda, Ryo
Hosotani, Kento
Fukano, Hanako
Hoshino, Yoshihiko
Hirabayashi, Aki
Suzuki, Masato
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Abstract
Genome mining of polyketide synthase-nonribosomal peptide synthetase (PKS-NRPS) in fungal endophyte Neopestalotiopsis olumideae strain BRIP 39872 identified seven new natural products (olumilides A–D, D1, D1’, D2) with pyrano[2,3-c]pyrrole scaffolds and their biosynthetic precursor preolumilide. Unlike known congeners, such as curvupallides, olumilides possess alkyl side chains with branched methyl groups and threonine-derived core scaffolds. Absolute configurations were determined by microED and ECD simulations, providing valuable information for further research focusing on the stereochemistry of PKS-NRPS reactions.
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Organic Letters
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27
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31
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© 2025 The Authors. Published by American Chemical Society. This publication is licensed under CC-BY-NC-ND 4.0.
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Shi, Y; Ozaki, T; Morishita, Y; Taniguchi, T; Sato, H; Aoyama, Y; Sugawara, A; Numata, K; Fuse, T; Matsuda, R; Hosotani, K; Fukano, H; Hoshino, Y; Hirabayashi, A; Suzuki, M; Yasuda, J; Yoshikawa, R; Hayashi, H; Kodama, EN; Shimotai, Y; Hamamoto, H; Davis, RA; Asai, T, Genome Mining-Based Discovery of Pyrano[2,3-c]pyrrole Type Natural Products Possessing Alkyl Side Chain with Branched Methyl Groups, Organic Letters, 2025, 27 (31), pp. 8580-8585