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Identification of Cyclopropane Formation in the Biosyntheses of Hormaomycins and Belactosins : Sequential Nitration and Cyclopropanation by Metalloenzymes

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Title: Identification of Cyclopropane Formation in the Biosyntheses of Hormaomycins and Belactosins : Sequential Nitration and Cyclopropanation by Metalloenzymes
Authors: Li, Xiaojun Browse this author
Shimaya, Ryo Browse this author
Dairi, Tohru Browse this author →KAKEN DB
Chang, Wei-chen Browse this author
Ogasawara, Yasushi Browse this author →KAKEN DB
Keywords: Biosynthesis
Natural products
Issue Date: 7-Feb-2022
Publisher: Wiley-Blackwell
Journal Title: Angewandte chemie-international edition
Volume: 61
Issue: 7
Start Page: e202113189
Publisher DOI: 10.1002/anie.202113189
Abstract: Hormaomycins and belactosins are peptide natural products that contain unusual cyclopropane moieties. Bioinformatics analysis of the corresponding biosynthetic gene clusters showed that two conserved genes, hrmI/belK and hrmJ/belL, were potential candidates for catalyzing cyclopropanation. Using in vivo and in vitro assays, the functions of HrmI/BelK and HrmJ/BelL were established. HrmI and BelK, which are heme oxygenase-like dinuclear iron enzymes, catalyze oxidation of the epsilon-amino group of l-lysine to afford l-6-nitronorleucine. Subsequently, HrmJ and BelL, which are iron- and alpha-ketoglutarate-dependent oxygenases, effectively convert l-6-nitronorleucine into 3-(trans-2-nitrocyclopropyl)-alanine through C4-C6 bond installation. These observations disclose a novel pathway of cyclopropane ring construction and exemplify the new chemistry involving metalloenzymes in natural product biosynthesis.
Rights: This is the peer reviewed version of the following article: X. Li, R. Shimaya, T. Dairi, W.-c. Chang, Y. Ogasawara, Angew. Chem. Int. Ed. 2022, 61, e202113189., which has been published in final form at This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions. This article may not be enhanced, enriched or otherwise transformed into a derivative work, without express permission from Wiley or by statutory rights under applicable legislation. Copyright notices must not be removed, obscured or modified. The article must be linked to Wiley’s version of record on Wiley Online Library and any embedding, framing or otherwise making available the article or pages thereof by third parties from platforms, services and websites other than Wiley Online Library must be prohibited.
Type: article (author version)
Appears in Collections:工学院・工学研究院 (Graduate School of Engineering / Faculty of Engineering) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 小笠原 泰志

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