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

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Title: Biosynthesis of the Carbonylmethylene Structure Found in the Ketomemicin Class of Pseudotripeptides
Authors: Kawata, Junpei Browse this author
Naoe, Taiki Browse this author
Ogasawara, Yasushi Browse this author
Dairi, Tohru Browse this author
Keywords: biosynthesis
enzymes
natural products
peptidomimetics
pseudopeptides
Issue Date: 13-Feb-2017
Publisher: Wiley-Blackwell
Journal Title: Angewandte chemie-international edition
Volume: 56
Issue: 8
Start Page: 2026
End Page: 2029
Publisher DOI: 10.1002/anie.201611005
PMID: 28097768
Abstract: 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.
Type: article (author version)
URI: http://hdl.handle.net/2115/68303
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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