2-methylgeranyl diphosphate | 59056-48-3

• 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: 2-methylgeranyl diphosphate
• 英文别名: phosphono [(2E,6E)-2,3,7,11-tetramethyldodeca-2,6,10-trienyl] hydrogen phosphate
• CAS: 59056-48-3
• 化学式: C₁₆H₃₀O₇P₂
• 分子量: 396.358
• InChiKey: NLEXDUMLYCKKMI-MQIHADEYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  25
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  2-methylgeranyl diphosphate 在 6His-tagged Pseudomonas fluorescens PfO-1 Pfl_1841 2-methylenebornane synthase 作用下， 以 正戊烷 为溶剂， 反应 12.0h， 以71%的产率得到(1S,4R)-1,7,7-Trimethyl-2-methylene-bicyclo[2.2.1]heptane
  参考文献：
  名称：

  Cloning and characterization of Pfl_1841, a 2-methylenebornane synthase in Pseudomonas fluorescens PfO-1

  摘要：

  The pfl_1841 gene from Pseudomonas fluorescens PfO-1 is the only gene in any of the three sequenced genomes of the Gram-negative bacterium P. fluorescens, that is, annotated as a putative terpene synthase. The predicted Pfl_1841 protein, which harbors the two strictly conserved divalent metal binding domains found in all terpene cyclases, is closely related to several known or presumed 2-methylisoborneol synthases, with the closest match being to the MOL protein of Micromonaspora olivasterospora KY11048 that has been implicated as a 2-methylenebornane synthase. A synthetic gene encoding P. fluorescens Pfl_1841 and optimized for expression in Escherichia coli was expressed and purified as an N-terminal His(6)-tagged protein. Incubation of recombinant Pfl_1841 with 2-methylgeranyl diphosphate produced 2-methylenebornane as the major product accompanied by 1-methylcamphene as well as other minor, monomethyl-homomonoterpene hydrocarbons and alcohols. The steady-state kinetic parameters for the Pfl_1841-catalyzed reaction were K(M)=110 +/- 13 nM and k(cat)=2.4 +/- 0.1 x 10(-2) s(-1). Attempts to identify the P. fluorescens SAM-dependent 2-methylgeranyl diphosphate synthase have so far been unsuccessful. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.05.084

文献信息

• Cloning and characterization of Pfl_1841, a 2-methylenebornane synthase in Pseudomonas fluorescens PfO-1
  作者：Wayne K.W. Chou、Haruo Ikeda、David E. Cane

  DOI：10.1016/j.tet.2011.05.084

  日期：2011.9

  The pfl_1841 gene from Pseudomonas fluorescens PfO-1 is the only gene in any of the three sequenced genomes of the Gram-negative bacterium P. fluorescens, that is, annotated as a putative terpene synthase. The predicted Pfl_1841 protein, which harbors the two strictly conserved divalent metal binding domains found in all terpene cyclases, is closely related to several known or presumed 2-methylisoborneol synthases, with the closest match being to the MOL protein of Micromonaspora olivasterospora KY11048 that has been implicated as a 2-methylenebornane synthase. A synthetic gene encoding P. fluorescens Pfl_1841 and optimized for expression in Escherichia coli was expressed and purified as an N-terminal His(6)-tagged protein. Incubation of recombinant Pfl_1841 with 2-methylgeranyl diphosphate produced 2-methylenebornane as the major product accompanied by 1-methylcamphene as well as other minor, monomethyl-homomonoterpene hydrocarbons and alcohols. The steady-state kinetic parameters for the Pfl_1841-catalyzed reaction were K(M)=110 +/- 13 nM and k(cat)=2.4 +/- 0.1 x 10(-2) s(-1). Attempts to identify the P. fluorescens SAM-dependent 2-methylgeranyl diphosphate synthase have so far been unsuccessful. (C) 2011 Elsevier Ltd. All rights reserved.