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Biosynthesis of the Carbonylmethylene Structure Found in the Ketomemicin Class of Pseudotripeptides

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タイトル: Biosynthesis of the Carbonylmethylene Structure Found in the Ketomemicin Class of Pseudotripeptides
著者: Kawata, Junpei 著作を一覧する
Naoe, Taiki 著作を一覧する
Ogasawara, Yasushi 著作を一覧する
Dairi, Tohru 著作を一覧する
キーワード: biosynthesis
enzymes
natural products
peptidomimetics
pseudopeptides
発行日: 2017年 2月13日
出版者: Wiley-Blackwell
誌名: Angewandte chemie-international edition
巻: 56
号: 8
開始ページ: 2026
終了ページ: 2029
出版社 DOI: 10.1002/anie.201611005
抄録: We recently discovered novel pseudotripeptides, the ketomemicins, which possess a C-terminal pseudodipeptide connected with a carbonylmethylene instead of an amide bond, through heterologous expression of gene clusters identified in actinobacteria. The carbonylmethylene structure is a stable isostere of the amide bond and its biological significance has been shown in several natural and synthetic products. Despite the biological importance of these compounds, little is known about how the carbonylmethylene structure is biosynthesized. In this work, we fully characterized the biosynthetic machinery of the pseudodipeptide. An aldolase, dehydratase, PLP-dependent glycine-C-acetyltransferase, and dehydrogenase were involved in the formation of the pseudodipeptide, with malonyl-CoA and phenylpyruvate as starter substrates.
Rights: This is the peer reviewed version of the following article: Angewandte Chemie International Edition Volume 56, Issue 8 February 13, 2017 , which has been published in final form at http://onlinelibrary.wiley.com/doi/10.1002/anie.201611005/abstract. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.
資料タイプ: article (author version)
URI: http://hdl.handle.net/2115/68303
出現コレクション:雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

提供者: 小笠原 泰志

 

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