farnesyl pyrophosphate | 104715-19-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: farnesyl pyrophosphate
• 英文别名: farnesyl diphosphate；FPP；(2E,6E)-3,7,11-Trimethyldodeca-2,6,10-trien-1-yl diphosphate；[oxido-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienoxy]phosphoryl] phosphate
• CAS: 104715-19-7
• 化学式: C₁₅H₂₅O₇P₂
• 分子量: 379.307
• InChiKey: VWFJDQUYCIWHTN-YFVJMOTDSA-K

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  122
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  farnesyl pyrophosphate 在 7-甲基-6-硫代鸟苷 、 purine nucleoside phosphorylase 、 YisP from Bacillus subtilis 、 magnesium chloride 作用下， 以 aq. buffer 为溶剂， 生成 反式,反式-金合欢醇
  参考文献：
  名称：

  Structural and Functional Analysis of Bacillus subtilis YisP Reveals a Role of Its Product in Biofilm Production

  摘要：

  YisP is involved in biofilm formation in Bacillus subtilis and has been predicted to produce C30 isoprenoids. We determined the structure of YisP and observed that it adopts the same fold as squalene and dehydrosqualene synthases. However, the first aspartate-rich motif found in essentially all isoprenoid synthases is aspartate poor in YisP and cannot catalyze head-to-head condensation reactions. We find that YisP acts as a phosphatase, catalyzing formation of farnesol from farnesyl diphosphate, and that it is the first phosphatase to adopt the fold seen in the head-to-head prenyl synthases. Farnesol restores biofilm formation in a Delta yisp mutant and modifies lipid membrane structure similarly to the virulence factor staphyloxanthin. This work clarifies the role of YisP in biofilm formation and suggests an intriguing possibility that many of the YisP-like homologs found in other bacteria may also have interesting products and functions.

  DOI：

  10.1016/j.chembiol.2014.08.018
• 作为产物：
  描述：

  (2E,6E)-Farnesyl phosphate 、 cytidine 5'-triphosphate 生成 farnesyl pyrophosphate 、 CDP
  参考文献：
  名称：

  法尼醇激酶参与拟南芥中的法尼醇代谢，ABA信号传导和花发育

  摘要：

  将高浓度对植物细胞有毒的法呢醇依次磷酸化为法呢基磷酸酯和法呢基二磷酸酯。然而，尚未鉴定出负责法尼醇的顺序磷酸化的基因，并且尚未完全阐明法尼醇磷酸化的生理作用。为了解决这些问题，我们确认了拟南芥（Arabidopsis thaliana）膜中存在法尼醇激酶活性，并鉴定了相应的基因（At5g58560，FOLK）。重组酵母细胞中的异源表达使法呢醇成为FOLK编码激酶的首选底物。此外，FOLK中的功能丧失突变该基因消除了法尼醇激酶活性，引起了脱落酸超敏性表型，并促进了水分胁迫条件下多余心皮的发育。在野生型植物中，外源脱落酸抑制FOLK基因表达。这些观察结果证明了法尼醇激酶在脱落酸信号的负调控中的作用，并提供了法尼醇代谢，非生物胁迫信号和花发育之间联系的分子证据。

  DOI：

  10.1111/j.1365-313x.2011.04572.x

文献信息

• Sesquiterpene Synthases Cop4 and Cop6 from Coprinus cinereus: Catalytic Promiscuity and Cyclization of Farnesyl Pyrophosphate Geometric Isomers
  作者：Fernando Lopez-Gallego、Sean A. Agger、Daniel Abate-Pella、Mark D. Distefano、Claudia Schmidt-Dannert

  DOI：10.1002/cbic.200900671

  日期：——

  Cyclization of FPP: Two new fungal sesquiterpene synthase are described that have opposite catalytic fidelities in the cyclization of farnesyl diphosphate. Catalytic promiscuity can be drastically reduced by changing the conditions of the reaction. Conversion of the FPP geometric isomers was found to proceed via opposite enantiomers of a cyclic carbocation intermediate that are rearranged to different

  FPP 的环化：描述了两种新的真菌倍半萜烯合酶，它们在二磷酸法呢酯的环化中具有相反的催化保真度。通过改变反应条件可以大大减少催化混杂。发现 FPP 几何异构体的转化是通过环状碳阳离子中间体的相反对映异构体进行的，这些对映异构体重新排列成不同的倍半萜烯产物。
• Mechanistic Investigations of Two Bacterial Diterpene Cyclases: Spiroviolene Synthase and Tsukubadiene Synthase
  作者：Patrick Rabe、Jan Rinkel、Etilia Dolja、Thomas Schmitz、Britta Nubbemeyer、T. Hoang Luu、Jeroen S. Dickschat

  DOI：10.1002/anie.201612439

  日期：2017.3.1

  two diterpene cyclases from streptomycetes—one with an unknown product that was identified as the spirocyclic hydrocarbon spiroviolene and one with the known product tsukubadiene—were investigated in detail by isotope labeling experiments. Although the structures of the products were very different, the cyclization mechanisms of both enzymes proceed through the same initial cyclization reactions, before

  通过同位素标记实验详细研究了链霉菌中的两种二萜环化酶的机理，一种是未知产物，被鉴定为螺环烃螺环戊烯，另一种是已知的tsukubadiene。尽管产物的结构非常不同，但是两种酶的环化机理都是通过相同的初始环化反应进行的，然后才趋向于各个产物，这反映在酶的密切系统发育关系中。
• Two Diterpene Synthases from <i>Chryseobacterium</i> : Chryseodiene Synthase and Wanjudiene Synthase
  作者：Lukas Lauterbach、Bernd Goldfuss、Jeroen S. Dickschat

  DOI：10.1002/anie.202004691

  日期：2020.7.13

  Two bacterial diterpene synthases (DTSs) from Chryseobacterium were characterised. The first enzyme yielded the new compound chryseodiene that closely resembles the known fusicoccane diterpenes from fungi, but its experimentally and computationally studied cyclisation mechanism is fundamentally different to the mechanism of fusicoccadiene synthase. The second enzyme produced wanjudiene, a diterpene

  表征了来自金黄杆菌的两种细菌二萜合酶 (DTS) 。第一种酶产生的新化合物 chryseodiene 与已知的来自真菌的 Fusicoccane 二萜非常相似，但其实验和计算研究的环化机制与 Fusicoccadiene 合酶的机制根本不同。除了最近从Allokutzneria albata 中发现的bonnadiene对映异构体的痕迹外，第二种酶还产生了 wanjudiene，一种具有新骨架的二萜烃。
• Induced-Fit Mechanism in Class I Terpene Cyclases
  作者：Philipp Baer、Patrick Rabe、Katrin Fischer、Christian A. Citron、Tim A. Klapschinski、Michael Groll、Jeroen S. Dickschat

  DOI：10.1002/anie.201403648

  日期：2014.7.14

  plants, including epi‐isozizaene synthase (3KB9), aristolochene synthase (4KUX), bornyl diphosphate synthase (1N20), limonene synthase (2ONG), 5‐epi‐aristolochene synthase (5EAT), and taxa‐4(5),11(12)‐diene synthase (3P5R). An elaborate structure‐based mutagenesis in combination with analysis of the distinct product spectra confirmed the mechanistic models of carbocation formation and stabilization in

  我们介绍了链霉菌链霉菌的selina-4（15），7（11）-二烯合酶（SdS）的晶体学和功能数据，其开放和闭合（配体结合）构象。我们可以通过阐明底物结合后G1 / 2螺旋断裂基序的重排来确定诱导拟合的机制。这种重排突出显示了一种新型的效应三联体，其包括焦磷酸盐传感器Arg178，接头Asp181和效应子Gly182-O。该结构基序在细菌，真菌和植物的I类萜烯环化酶中严格保守，包括表异异氮烯合酶（3KB9），马兜铃属合酶（4KUX），冰片烯基二磷酸合酶（1N20），柠檬烯合酶（2ONG），5表位-aristolochene合酶（5EAT）和分类单元4（5），11（12）-二烯合酶（3P5R）。
• Substrate geometry controls the cyclization cascade in multiproduct terpene synthases from Zea mays
  作者：Abith Vattekkatte、Nathalie Gatto、Tobias G. Köllner、Jörg Degenhardt、Jonathan Gershenzon、Wilhelm Boland

  DOI：10.1039/c5ob00711a

  日期：——

  Multiproduct terpene synthases on incubation with (2Z) substrates showed enhanced enzymatic turnover with distinct preference for cyclic products than corresponding (2E) substrates.

  多产品萜烯合成酶在与（2Z）底物孵育后，表现出增强的酶促转化能力，对环状产物的偏好明显高于相应的（2E）底物。