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对异腈基团生物合成及其机制的当前理解。

Current Understanding toward Isonitrile Group Biosynthesis and Mechanism.

作者信息

Chen Tzu-Yu, Chen Jinfeng, Tang Yijie, Zhou Jiahai, Guo Yisong, Chang Wei-Chen

机构信息

Department of Chemistry, North Carolina State University Raleigh, NC 27695, U.S.A.

State Key Laboratory of Bio-organic and Natural Products Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Shanghai 200032, China.

出版信息

Chin J Chem. 2021 Feb;39(2):463-472. doi: 10.1002/cjoc.202000448. Epub 2020 Sep 24.

Abstract

Isonitrile group has been identified in many natural products. Due to the broad reactivity of N≡C triple bond, these natural products have valuable pharmaceutical potentials. This review summarizes the current biosynthetic pathways and the corresponding enzymes that are responsible for isonitrile-containing natural product generation. Based on the strategies utilized, two fundamentally distinctive approaches are discussed. In addition, recent progress in elucidating isonitrile group formation mechanisms is also presented.

摘要

异腈基团已在许多天然产物中被鉴定出来。由于N≡C三键具有广泛的反应活性,这些天然产物具有宝贵的药用潜力。本综述总结了目前负责含异腈天然产物生成的生物合成途径及相应的酶。基于所采用的策略,讨论了两种根本不同的方法。此外,还介绍了在阐明异腈基团形成机制方面的最新进展。

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本文引用的文献

1
Pathway from N-Alkylglycine to Alkylisonitrile Catalyzed by Iron(II) and 2-Oxoglutarate-Dependent Oxygenases.
Angew Chem Int Ed Engl. 2020 May 4;59(19):7367-7371. doi: 10.1002/anie.201914896. Epub 2020 Mar 10.
2
Two-Enzyme Pathway Links l-Arginine to Nitric Oxide in N-Nitroso Biosynthesis.
J Am Chem Soc. 2019 Mar 6;141(9):4026-4033. doi: 10.1021/jacs.8b13049. Epub 2019 Feb 21.
3
An N-nitrosating metalloenzyme constructs the pharmacophore of streptozotocin.
Nature. 2019 Feb;566(7742):94-99. doi: 10.1038/s41586-019-0894-z. Epub 2019 Feb 6.
4
Chemical Diversification Based on Substrate Promiscuity of a Standalone Adenylation Domain in a Reconstituted NRPS System.
ACS Chem Biol. 2019 Feb 15;14(2):256-265. doi: 10.1021/acschembio.8b00938. Epub 2019 Feb 4.
5
Isonitrile-functionalized tyrosine modulates swarming motility and quorum sensing in Pseudomonas aeruginosa.
Microb Pathog. 2019 Feb;127:288-295. doi: 10.1016/j.micpath.2018.12.001. Epub 2018 Dec 4.
6
Amycomicin is a potent and specific antibiotic discovered with a targeted interaction screen.
Proc Natl Acad Sci U S A. 2018 Oct 2;115(40):10124-10129. doi: 10.1073/pnas.1807613115. Epub 2018 Sep 18.
7
Asymmetric phosphoric acid-catalyzed four-component Ugi reaction.
Science. 2018 Sep 14;361(6407). doi: 10.1126/science.aas8707.
8
Isonitrile Formation by a Non-Heme Iron(II)-Dependent Oxidase/Decarboxylase.
Angew Chem Int Ed Engl. 2018 Jul 26;57(31):9707-9710. doi: 10.1002/anie.201804307. Epub 2018 Jul 3.
9
Tandem Hydration of Diisonitriles Triggered by Isonitrile Hydratase in Streptomyces thioluteus.
Org Lett. 2018 Jun 15;20(12):3562-3565. doi: 10.1021/acs.orglett.8b01341. Epub 2018 Jun 4.
10
Fungal Isocyanide Synthases and Xanthocillin Biosynthesis in Aspergillus fumigatus.
mBio. 2018 May 29;9(3):e00785-18. doi: 10.1128/mBio.00785-18.

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