geranylfarnesyl diphosphate

• 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: geranylfarnesyl diphosphate
• 英文别名: GFPP；all-trans-Pentaprenyl diphosphate；[(2E,6E,10E,14E)-3,7,11,15,19-pentamethylicosa-2,6,10,14,18-pentaenyl] phosphono hydrogen phosphate
• 化学式: C₂₅H₄₄O₇P₂
• 分子量: 518.568
• InChiKey: JMVSBFJBMXQNJW-GIXZANJISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  34
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  113
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  geranylfarnesyl diphosphate 在 Bacillus clausii tetraprenyl-β-curcumene synthase 、 氯化铵 、 magnesium chloride 、 1,4-二巯基-2,3-丁二醇 作用下， 反应 1.0h， 生成 β-geranylfarnesene
  参考文献：
  名称：

  克劳氏芽孢杆菌新型酯化三萜/三萜合酶的鉴定

  摘要：

  碱性酶：来自嗜碱芽孢杆菌的四异戊二烯-β-姜黄素合酶同源物催化香叶基法呢基二磷酸酯和六异戊二烯基二磷酸酯转化为新的头尾无环环丁烯三萜烯和三萜烯。四氢戊二烯-β-姜黄素合酶同源物代表了一个新的萜烯合酶家族，不仅形成了倍半萜烯，而且还形成了酯基萜烯和三萜烯。

  DOI：

  10.1002/cbic.201300035

文献信息

• Subrutilane—A Hexacyclic Sesterterpene from <i>Streptomyces subrutilus</i>
  作者：Binbin Gu、Bernd Goldfuss、Gregor Schnakenburg、Jeroen S. Dickschat

  DOI：10.1002/anie.202313789

  日期：2023.11.27

  Genome mining uncovered a terpene synthase from Streptomyces subrutilus that produces the first known hexacyclic sesterterpene with no double bonds as the main product, as well as eight pentacyclic products. Isotopic labelling experiments and DFT calculations revealed a cyclisation cascade via several well-stabilised secondary cations. The enzyme also converted several substrate analogues into sesterterpenoid

  基因组挖掘发现了来自Subrutilus 链霉菌的萜烯合酶，它产生第一个已知的不带双键的六环二倍萜作为主要产物，以及八种五环产物。同位素标记实验和 DFT 计算揭示了通过几个稳定良好的次级阳离子的环化级联。该酶还将几种底物类似物转化为二元萜类化合物。
• Enzymatic syntheses of unnatural head-to-tail pentacyclic triterpenes by tetraprenyl-β-curcumene cyclase
  作者：Wataru Okamoto、Tsutomu Sato

  DOI：10.1016/j.tetlet.2013.09.135

  日期：2013.12

  Little is known of the biosynthesis of sesquarterpenes and the synthesis of unnatural terpenoids by sesquarterpene biosynthetic enzymes has not yet been reported. In this study, the enzymatic cyclization of head-to-tail acyclic triterpene beta-hexaprene a natural product isolated from Bacillus clausii-using tetraprenyl-beta-curcumene cyclase (TC) from Bacillus subtilis resulted in the formation of two unnatural pentacyclic triterpenes. It was revealed that B. subtilis TC, which forms tetracyclic terpenoid scaffold from tetraprenyl-beta-curcumene in vivo, could be used to construct the 6/6/6/6/6-fused pentacyclic scaffold in vitro, suggesting that the active site cavity of TC has sufficient space to accommodate this unnatural pentacyclic scaffold. This is the first report demonstrating the utility of a sesquarterpene cyclase toward the synthesis of unnatural terpenoids. (C) 2013 Elsevier Ltd. All rights reserved.
• COMPOSITION COMPRISING A SESTERTERPENE AND USE THEREOF AS ANTIBIOTIC AND ANTIFUNGAL ADJUVANT
  申请人：Rode Pharma S.r.l.

  公开号：EP2863904A1

  公开（公告）日：2015-04-29
• USE OF GASCARDIC ACID AS ANTIBIOTIC AND ANTIFUNGAL ADJUVANT
  申请人：Rode Pharma S.r.l.

  公开号：EP2863904B1

  公开（公告）日：2018-02-21
• US9775348B2
  申请人：——

  公开号：US9775348B2

  公开（公告）日：2017-10-03