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大肠杆菌中menaquinone 的生物合成：SEPHCHC 一个难以捉摸的异构体的鉴定。

Biosynthesis of Menaquinone in E. coli: Identification of an Elusive Isomer of SEPHCHC.

机构信息

Institute of Pharmaceutical Sciences, Albert-Ludwigs-Universität Freiburg, Albertstrasse 25, 79104, Freiburg, Germany.

Present address: INCITAP-CONICET, Departamento de Química, Facultad de Ciencias Exactas y Naturales, Universidad Nacional de La Pampa, Av. Uruguay 151, 6300, Santa Rosa, La Pampa, Argentina.

出版信息

Chembiochem. 2022 Sep 16;23(18):e202200181. doi: 10.1002/cbic.202200181. Epub 2022 Jul 28.

DOI:10.1002/cbic.202200181
PMID:35901288
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9544450/
Abstract

In the biosynthesis of menaquinone in bacteria, the thiamine diphosphate-dependent enzyme MenD catalyzes the decarboxylative carboligation of α-ketoglutarate and isochorismate to (1R,2S,5S,6S)-2-succinyl-5-enolpyruvyl-6-hydroxycyclohex-3-ene-1-carboxylate (SEPHCHC). The regioisomer of SEPHCHC, namely (1R,5S,6S)-2-succinyl-5-enolpyruvyl-6-hydroxycyclohex-2-ene-1-carboxylate (iso-SEPHCHC), has been considered as a possible product, however, its existence has been doubtful due to a spontaneous elimination of pyruvate from SEPHCHC to 2-succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate (SHCHC). In this work, the regioisomer iso-SEPHCHC was distinguished from SEPHCHC by liquid chromatography-tandem mass spectrometry. Iso-SEPHCHC was purified and identified by NMR spectroscopy. Just as SEPHCHC remained hidden as a MenD product for more than two decades, its regioisomer iso-SEPHCHC has remained until now.

摘要

在细菌menaquinone 的生物合成中，依赖于硫胺素二磷酸的酶 MenD 催化 α-酮戊二酸和异分支酸的脱羧碳连接，生成（1R,2S,5S,6S）-2-琥珀酰基-5-烯醇丙酮酰基-6-羟基环己-3-烯-1-羧酸酯（SEPHCHC）。SEPHCHC 的差向异构体，即（1R,5S,6S）-2-琥珀酰基-5-烯醇丙酮酰基-6-羟基环己-2-烯-1-羧酸酯（iso-SEPHCHC），被认为是一种可能的产物，但其存在一直存在疑问，因为 SEPHCHC 中的丙酮酸会自发消除，生成 2-琥珀酰基-6-羟基-2,4-环己二烯-1-羧酸酯（SHCHC）。在这项工作中，通过液相色谱-串联质谱法将差向异构体 iso-SEPHCHC 与 SEPHCHC 区分开来。iso-SEPHCHC 通过 NMR 光谱进行了纯化和鉴定。正如 SEPHCHC 作为 MenD 的产物隐藏了二十多年一样，其差向异构体 iso-SEPHCHC 至今仍未被发现。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c62c/9544450/b1772a1049c0/CBIC-23-0-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c62c/9544450/4ae2ec6ae555/CBIC-23-0-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c62c/9544450/6844eb29039f/CBIC-23-0-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c62c/9544450/1e8e680fb5f4/CBIC-23-0-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c62c/9544450/b1772a1049c0/CBIC-23-0-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c62c/9544450/4ae2ec6ae555/CBIC-23-0-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c62c/9544450/6844eb29039f/CBIC-23-0-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c62c/9544450/1e8e680fb5f4/CBIC-23-0-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c62c/9544450/b1772a1049c0/CBIC-23-0-g004.jpg

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