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在二萜类信息素索布拉烯的生物合成过程中,立体选择性去质子化引入了一个不寻常的8,9双键。

Stereoselective deprotonation installs an unusual -8,9 double bond during biosynthesis of the diterpene pheromone sobralene.

作者信息

Da Silva Igor F P, Ducker Charles, Pickett John A, Santana Antônio E G, Oldham Neil J

机构信息

School of Chemistry, University of Nottingham, University Park, Nottingham, NG7 2RD, UK.

Institute of Chemistry and Biotechnology, Federal University of Alagoas A. C. Simões Campus, Maceió, AL 57072-970, Brazil.

出版信息

Chem Commun (Camb). 2025 Jul 11. doi: 10.1039/d5cc03298a.

DOI:10.1039/d5cc03298a
PMID:40641443
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC12246896/
Abstract

A terpene synthase from the sandfly , catalyses stereoselective removal of the -S proton from C8 of geranylgeranyl diphosphate to generate the characteristic ()-8,9 double bond seen in the diterpene pheromone sobralene. Retention of deuterium in structurally related minor products demonstrates that they are not produced sobralene, but are made directly by the enzyme.

摘要

一种来自沙蝇的萜烯合酶,催化从香叶基香叶基二磷酸的C8上立体选择性去除-S质子,以生成在二萜信息素索布烯中可见的特征性()-8,9双键。结构相关的次要产物中氘的保留表明,它们不是由索布烯产生的,而是由该酶直接产生的。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/15bb/12246896/6f59ddf63c1a/d5cc03298a-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/15bb/12246896/d66d4e0d56a4/d5cc03298a-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/15bb/12246896/d7d016c259f6/d5cc03298a-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/15bb/12246896/8a3812caac33/d5cc03298a-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/15bb/12246896/6f59ddf63c1a/d5cc03298a-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/15bb/12246896/d66d4e0d56a4/d5cc03298a-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/15bb/12246896/d7d016c259f6/d5cc03298a-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/15bb/12246896/8a3812caac33/d5cc03298a-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/15bb/12246896/6f59ddf63c1a/d5cc03298a-s3.jpg

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A diterpene synthase from the sandfly produces the pheromone sobralene.一种来自沙蝇的二萜合酶可产生信息素索布拉烯。
Proc Natl Acad Sci U S A. 2024 Mar 19;121(12):e2322453121. doi: 10.1073/pnas.2322453121. Epub 2024 Mar 12.
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Characterisation of geranylgeranyl diphosphate synthase from the sandfly Lutzomyia longipalpis.来自长须罗蛉的香叶基香叶基二磷酸合酶的特性分析。
Insect Biochem Mol Biol. 2023 Oct;161:104001. doi: 10.1016/j.ibmb.2023.104001. Epub 2023 Aug 22.
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Emergence of terpene chemical communication in insects: Evolutionary recruitment of isoprenoid metabolism.萜类化合物在昆虫化学通讯中的出现:异戊二烯代谢的进化招募。
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