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二萜螺环维利醇的环化机制修订及质谱裂解研究。

Revision of the Cyclisation Mechanism for the Diterpene Spiroviolene and Investigations of Its Mass Spectrometric Fragmentation.

机构信息

Kekulé Institute for Organic Chemistry and Biochemistry, University of Bonn, Gerhard-Domagk-Straße 1, 53121, Bonn, Germany.

出版信息

Chembiochem. 2021 Mar 2;22(5):850-854. doi: 10.1002/cbic.202000682. Epub 2020 Nov 10.

DOI:10.1002/cbic.202000682
PMID:33084237
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7983979/
Abstract

The diterpene spiroviolene, its diterpene synthase from Streptomyces violens and the experimentally determined terpene cyclisation mechanism were reported in 2017. Recently, the structure of spiroviolene was revised based on a total synthesis, with consequences for the cyclisation mechanism. Herein, a reinvestigation of the terpene cyclisation to spiroviolene and the mass spectrometric fragmentation mechanism investigated by C-labelling experiments are presented.

摘要

2017 年报道了二萜螺环维利烯、其来源于浅青紫链霉菌的二萜合酶以及实验确定的萜类环化机制。最近，基于全合成对螺环维利烯的结构进行了修订，这对环化机制有影响。本文通过 C 标记实验重新研究了萜类化合物向螺环维利烯的环化以及质谱碎裂机制。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e9fa/7983979/ecab4057520e/CBIC-22-850-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e9fa/7983979/e5737e5e0162/CBIC-22-850-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e9fa/7983979/410e3f3abe57/CBIC-22-850-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e9fa/7983979/619a84af9e08/CBIC-22-850-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e9fa/7983979/55c3785dfa54/CBIC-22-850-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e9fa/7983979/31f640ef6b3e/CBIC-22-850-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e9fa/7983979/94faf99aff35/CBIC-22-850-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e9fa/7983979/ecab4057520e/CBIC-22-850-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e9fa/7983979/e5737e5e0162/CBIC-22-850-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e9fa/7983979/410e3f3abe57/CBIC-22-850-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e9fa/7983979/619a84af9e08/CBIC-22-850-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e9fa/7983979/55c3785dfa54/CBIC-22-850-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e9fa/7983979/31f640ef6b3e/CBIC-22-850-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e9fa/7983979/94faf99aff35/CBIC-22-850-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e9fa/7983979/ecab4057520e/CBIC-22-850-g004.jpg

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本文引用的文献

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Chem Sci. 2020 Sep 30;11(40):10939-10944. doi: 10.1039/d0sc04686h.
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Terpene Synthase Genes Originated from Bacteria through Horizontal Gene Transfer Contribute to Terpenoid Diversity in Fungi.萜烯合酶基因通过水平基因转移起源于细菌，有助于真菌萜类化合物的多样性。
Sci Rep. 2019 Jun 25;9(1):9223. doi: 10.1038/s41598-019-45532-1.
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Bacterial Diterpene Biosynthesis.细菌二萜生物合成。
J Am Chem Soc. 2021 Mar 17;143(10):3794-3807. doi: 10.1021/jacs.0c10214. Epub 2021 Jan 26.
Angew Chem Int Ed Engl. 2019 Nov 4;58(45):15964-15976. doi: 10.1002/anie.201905312. Epub 2019 Aug 1.
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Diterpene Biosynthesis in Actinomycetes: Studies on Cattleyene Synthase and Phomopsene Synthase.放线菌二萜生物合成：卡特烯合酶和腐皮镰刀菌素合酶的研究。
Angew Chem Int Ed Engl. 2019 Jul 1;58(27):9230-9233. doi: 10.1002/anie.201902950. Epub 2019 May 24.
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Addressing the Chemistry of Germacrene A by Isotope Labeling Experiments.通过同位素标记实验研究吉马烯A的化学性质。
Org Lett. 2019 Apr 5;21(7):2426-2429. doi: 10.1021/acs.orglett.9b00725. Epub 2019 Mar 12.
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