Cleistantha-8,12-diene 的形成中的欺骗性复杂性。
Deceptive Complexity in Formation of Cleistantha-8,12-diene.
机构信息
State Key Laboratory of Crop Gene Exploration and Utilization in Southwest China, College of Agronomy, Sichuan Agricultural University, Chengdu, Sichuan 611130, China.
Roy J. Carver Department of Biochemistry, Biophysics & Molecular Biology, Iowa State University, Ames, Iowa 50011, United States.
出版信息
Org Lett. 2022 Apr 15;24(14):2646-2649. doi: 10.1021/acs.orglett.2c00680. Epub 2022 Apr 6.
Abstract
A barley diterpene synthase (HvKSL4) was found to produce (14)-cleistantha-8,12-diene (). Formation of the nearly planar cyclohexa-1,4-diene configuration leaves the ring poised for aromatization, but necessitates a deceptively complicated series of rearrangements steered through a complex energetic landscape, as elucidated here through quantum chemical calculations and labeling studies.
摘要
大麦二萜合酶（HvKSL4）被发现可以合成（14）-Cleistantha-8,12-二烯（）。几乎呈平面的环己-1,4-二烯构型的形成使环处于芳构化的位置，但需要通过复杂的能量景观进行一系列复杂的重排，正如通过量子化学计算和标记研究在这里阐明的那样。
相似文献
1
Deceptive Complexity in Formation of Cleistantha-8,12-diene.Cleistantha-8,12-diene 的形成中的欺骗性复杂性。
Org Lett. 2022 Apr 15;24(14):2646-2649. doi: 10.1021/acs.orglett.2c00680. Epub 2022 Apr 6.
2
Piriformospora indica requires kaurene synthase activity for successful plant colonization.印度梨形孢成功定殖于植物需要贝壳杉烯合酶活性。
Plant Physiol Biochem. 2016 May;102:151-60. doi: 10.1016/j.plaphy.2016.02.017. Epub 2016 Feb 16.
3
Biosynthesis of rice phytoalexins: identification of putative diterpene hydrocarbon precursors.水稻植保素的生物合成：推定的二萜烃前体的鉴定。
Arch Biochem Biophys. 1992 Mar;293(2):320-32. doi: 10.1016/0003-9861(92)90402-i.
4
A Clade II-D Fungal Chimeric Diterpene Synthase from Colletotrichum gloeosporioides Produces Dolasta-1(15),8-diene.胶孢炭疽菌属的 II-D 类真菌嵌合二萜合酶产生多拉甾烷-1(15),8-二烯。
Angew Chem Int Ed Engl. 2018 Nov 26;57(48):15887-15890. doi: 10.1002/anie.201809954. Epub 2018 Oct 26.
5
Novel cassane and cleistanthane diterpenes from Myrospermum frutescens: absolute stereochemistry of the cassane diterpene series.来自灌木状秘鲁香脂的新型乌檀烷型和闭花木烷型二萜：乌檀烷型二萜系列的绝对立体化学
J Nat Prod. 2004 Oct;67(10):1711-5. doi: 10.1021/np049890c.
6
Cassane diterpenes from Caesalpinia platyloba.来自 Platyloba Caesalpinia 的羽扇豆烷二萜。
Phytochemistry. 2013 Dec;96:397-403. doi: 10.1016/j.phytochem.2013.09.028. Epub 2013 Oct 28.
7
Bromination of Cyclohexa-1,3-diene and (,)-Cyclohexa-3,5-diene-1,2-diol.环己-1,3-二烯和（±）-环己-3,5-二烯-1,2-二醇的溴化反应
J Org Chem. 1999 Jul 9;64(14):5245-5250. doi: 10.1021/jo990473s.
8
Premutilin Synthase: Ring Rearrangement by a Class II Diterpene Cyclase.普瑞马林合酶：通过 II 类二萜环化酶的环重排。
Org Lett. 2018 Feb 16;20(4):1200-1202. doi: 10.1021/acs.orglett.8b00121. Epub 2018 Feb 1.
9
A copal-8-ol diphosphate synthase from the angiosperm Cistus creticus subsp. creticus is a putative key enzyme for the formation of pharmacologically active, oxygen-containing labdane-type diterpenes.来自被子植物 Cretan 乳香黄连木亚种的 copal-8-ol 二磷酸合酶是形成具有药理活性的含氧 labdane 型二萜的假定关键酶。
Plant Physiol. 2010 Sep;154(1):301-10. doi: 10.1104/pp.110.159566. Epub 2010 Jul 1.
10
Purification and characterization of taxa-4(5),11(12)-diene synthase from Pacific yew (Taxus brevifolia) that catalyzes the first committed step of taxol biosynthesis.从太平洋紫杉（短叶红豆杉）中纯化和鉴定催化紫杉醇生物合成第一步关键反应的紫杉-4(5),11(12)-二烯合酶。
Arch Biochem Biophys. 1995 Oct 1;322(2):437-44. doi: 10.1006/abbi.1995.1486.
本文引用的文献
1
A (conditional) role for labdane-related diterpenoid natural products in rice stomatal closure.赖百当类二萜天然产物在水稻气孔关闭中的（条件性）作用。
New Phytol. 2021 Apr;230(2):698-709. doi: 10.1111/nph.17196. Epub 2021 Feb 12.
2
Specialized diterpenoid metabolism in monocot crops: Biosynthesis and chemical diversity.单子叶作物中萜类化合物的特化代谢：生物合成与化学多样性。
Phytochemistry. 2020 Apr;172:112289. doi: 10.1016/j.phytochem.2020.112289. Epub 2020 Feb 6.
3
A Branched Diterpene Cascade: The Mechanism of Spinodiene Synthase from Saccharopolyspora spinosa.支化二萜级联反应：来源于嗜热放线菌的螺环二烯合酶的作用机制。
Angew Chem Int Ed Engl. 2019 Jan 8;58(2):452-455. doi: 10.1002/anie.201812216. Epub 2018 Dec 6.
4
Structural and Chemical Biology of Terpenoid Cyclases.萜类环化酶的结构与化学生物学
Chem Rev. 2017 Sep 13;117(17):11570-11648. doi: 10.1021/acs.chemrev.7b00287. Epub 2017 Aug 25.
5
Mechanistic Characterization of Two Chimeric Sesterterpene Synthases from Penicillium.青霉属两种嵌合倍半萜合酶的机制表征
Chemistry. 2017 Jul 26;23(42):10053-10057. doi: 10.1002/chem.201702766. Epub 2017 Jul 3.
6
Mechanistic Investigations of Two Bacterial Diterpene Cyclases: Spiroviolene Synthase and Tsukubadiene Synthase.两种细菌二萜环化酶的机理研究：螺环戊烯酮合酶和紫檀烯合酶。
Angew Chem Int Ed Engl. 2017 Mar 1;56(10):2776-2779. doi: 10.1002/anie.201612439. Epub 2017 Jan 31.
7
Piriformospora indica requires kaurene synthase activity for successful plant colonization.印度梨形孢成功定殖于植物需要贝壳杉烯合酶活性。
Plant Physiol Biochem. 2016 May;102:151-60. doi: 10.1016/j.plaphy.2016.02.017. Epub 2016 Feb 16.
8
Product Rearrangement from Altering a Single Residue in the Rice syn-Copalyl Diphosphate Synthase.通过改变水稻顺式-柯巴基焦磷酸合酶中的单个残基实现产物重排。
Org Lett. 2016 Mar 4;18(5):1060-3. doi: 10.1021/acs.orglett.6b00181. Epub 2016 Feb 15.
9
Managing the computational chemistry big data problem: the ioChem-BD platform.解决计算化学大数据问题：ioChem-BD平台。
J Chem Inf Model. 2015 Jan 26;55(1):95-103. doi: 10.1021/ci500593j. Epub 2014 Dec 15.
10
To gibberellins and beyond! Surveying the evolution of (di)terpenoid metabolism.向赤霉素进发！（二）萜类化合物代谢的进化综述。
Annu Rev Plant Biol. 2014;65:259-86. doi: 10.1146/annurev-arplant-050213-035705. Epub 2014 Jan 22.
Zotero 插件