hexaprenyl diphosphate | 301177-88-8

• 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: hexaprenyl diphosphate
• 英文别名: hexaprenyl pyrophosphate；3,7,11,15,19,23-Hexamethyltetracosa-2,6,10,14,18,22-hexaenyl phosphono hydrogen phosphate
• CAS: 301177-88-8
• 化学式: C₃₀H₅₂O₇P₂
• 分子量: 586.686
• InChiKey: NGFSMHKFTZROKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  39
• 可旋转键数：
  20
• 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：

  hexaprenyl 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-hexaprene
  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

• The Mechanism of Action of Lysobactin
  作者：Wonsik Lee、Kaitlin Schaefer、Yuan Qiao、Veerasak Srisuknimit、Heinrich Steinmetz、Rolf Müller、Daniel Kahne、Suzanne Walker

  DOI：10.1021/jacs.5b11807

  日期：2016.1.13

  Lysobactin, also known as katanosin B, is a potent antibiotic with in vivo efficacy against Staphylococcus aureus and Streptococcus pneumoniae. It was previously shown to inhibit peptidoglycan (PG) biosynthesis, but its molecular mechanism of action has not been established. Using enzyme inhibition assays, we show that lysobactin forms 1:1 complexes with Lipid I, Lipid II, and Lipid IIAWTA, substrates in the PG and wall teichoic acid (WTA) biosynthetic pathways. Therefore, lysobactin, like ramoplanin and teixobactin, recognizes the reducing end of lipid-linked cell wall precursors. We show that despite its ability to bind precursors from different pathways, lysobactin's cellular mechanism of killing is due exclusively to Lipid II binding, which causes septal defects and catastrophic cell envelope damage.
• 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.
• Identification of Novel Sesterterpene/Triterpene Synthase from<i>Bacillus clausii</i>
  作者：Tsutomu Sato、Hiroaki Yamaga、Shoji Kashima、Yusuke Murata、Tetsuro Shinada、Chiaki Nakano、Tsutomu Hoshino

  DOI：10.1002/cbic.201300035

  日期：2013.5.10

  tetraprenyl‐β‐curcumene synthase homologue from the alkalophilic Bacillus clausii catalyses conversions of a geranylfarnesyl diphosphate and a hexaprenyl diphosphate into novel head‐to‐tail acyclic sesterterpene and triterpene. Tetraprenyl‐β‐curcumene synthase homologues represent a new family of terpene synthases that form not only sesquarterpene but also sesterterpene and triterpene.

  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。