dimethylallyl diphosphate | 780724-90-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: dimethylallyl diphosphate
• 英文别名: Bis(3-methylbut-2-enyl) hydrogen phosphate
• CAS: 780724-90-5
• 化学式: C₁₀H₁₉O₄P
• 分子量: 234.232
• InChiKey: MRWRSBWKMOTRAL-UHFFFAOYSA-N

物化性质

• 沸点：
  307.5±45.0 °C(Predicted)
• 密度：
  1.090±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  松属素 、 dimethylallyl diphosphate 在 Sophora flavesvens microsomes 、 magnesium chloride 作用下， 以 乙醇 、 水 为溶剂， 生成 5,7-dihydroxy-8-C-prenylflavanone
  参考文献：
  名称：

  Flavanone 8-dimethylallyltransferase in Sophora flavescens cell suspension cultures

  摘要：

  Dimethylallyl diphosphate: naringenin 8-dimethylallyltransferase (EC 2.5.1) was characterized. The enzyme was enantiospecific for (-)-(2S)-naringenin and utilized 3,3-dimethylallyl diphosphate as sole prenyl donor. It required Mg2+ (optimum concentration, 10 mM), and has an optimum pH of 9-10. The apparent K-m values for 3,3-dimethylallyl diphosphate and naringenin were 120 and 36 mu M, respectively. The microsomal fraction prenylated several other flavanones at the C-8 position less effectively as compared with naringenin. Interestingly, when 2'-hydroxynaringenin was used as a prenyl acceptor, the 8-lavandulyl (sophoraflavanone G) and the 6-dimethylallyl derivatives were formed, together with the 8-dimethylallyl derivative, leachianone G. These results suggest that the 2'-hydroxy group of naringenin plays an important role for the formation of a lavandulyl group. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(00)00198-9
• 作为产物：
  描述：

  在 吡啶 、 碘 作用下， 生成 dimethylallyl diphosphate
  参考文献：
  名称：

  Nakatani, Yoichi; Plobeck, Niklas; Eifler, Stephane, Phosphorus, Sulfur and Silicon and the Related Elements, 1993, vol. 77, # 1-4, p. 125 - 128

  摘要：

  DOI：

文献信息

• Synthesis of isoprenoids and derivatives
  申请人：William Marsh Rice University

  公开号：US11046978B2

  公开（公告）日：2021-06-29

  This disclosure generally relates to the use of enzyme combinations or recombinant microbes comprising same to make isoprenoid precursors, isoprenoids and derivatives thereof including prenylated aromatic compounds. Novel metabolic pathways exploiting Claisen, aldol, and acyioin condensations are used instead of the natural mevalonate (MVA) pathway or 1-deoxy-d-xylulose 5-phosphate (DXP) pathways for generating isoprenoid precursors such as isopentenyl pyrophosphate (IPP), dimethylallyl pyrophosphate (DMAPP), and geranyl pyrophosphate (GPP). These pathways have the potential for better carbon and or energy efficiency than native pathways. Both decarboxylative and non-carboxylative condensations are utilized, enabling product synthesis from a number of different starting compounds. These condensation reactions serve as a platform for the synthesis of isoprenoid precursors when utilized in combination with a variety of metabolic pathways and enzymes for carbon rearrangement and the addition/removal of functional groups. Isoprenoid alcohols are key intermediary products for the production of isoprenoid precursors in these novel synthetic metabolic pathways.

  本公开内容一般涉及使用酶组合或包含酶组合的重组微生物来制造异戊烯前体、异戊烯及其衍生物，包括前炔基芳香族化合物。利用克来森缩合、醛醇缩合和酰亚胺缩合的新型代谢途径取代了天然的甲羟戊酸（MVA）途径或 1-脱氧-d-木酮糖-5-磷酸（DXP）途径，用于生成焦磷酸异戊烯酯（IPP）、焦磷酸二甲基烯丙基酯（DMAPP）和焦磷酸香叶酯（GPP）等异戊烯前体。与原生途径相比，这些途径具有更高的碳效率和能量效率。利用脱羧和非羧缩合反应，可以从多种不同的起始化合物中合成产品。这些缩合反应可作为合成异戊二烯前体的平台，与各种代谢途径和酶结合使用，进行碳重排和官能团的添加/去除。在这些新型合成代谢途径中，异戊二烯醇是生产异戊二烯前体的关键中间产物。
• Sodium di-polyprenyl phosphates form “primitive” membranes
  作者：Niklas Plobeck、Stéphane Eifler、Alain Brisson、Yoichi Nakatani、Guy Ourisson

  DOI：10.1016/s0040-4039(00)79146-5

  日期：1992.9

  The bis phosphoric esters of dimethylallyl alcohol, isopentenol, geraniol, farnesol and geranylgeraniol have been prepared through the phosphites in order to evalUate their phase properties in water. The sodium and calcium salts of the first two are soluble in water; the others easily form closed vesicles. These could be representative of "primitive" biomcmbranes.
• MICROBIAL SYNTHESIS OF ISOPRENOID PRECURSORS, ISOPRENOIDS AND DERIVATIVES INCLUDING PRENYLATED AROMATIC COMPOUNDS
  申请人：William Marsh Rice University

  公开号：US20190352679A1

  公开（公告）日：2019-11-21

  This disclosure generally relates to the use of enzyme combinations or recombinant microbes comprising same to make isoprenoid precursors, isoprenoids and derivatives thereof including prenylated aromatic compounds. Novel metabolic pathways exploiting Claisen, aldol, and acyioin condensations are used instead of the natural mevalonate (MVA) pathway or 1-deoxy-d-xylulose 5-phosphate (DXP) pathways for generating isoprenoid precursors such as isopentenyl pyrophosphate (IPP), dimethylallyl pyrophosphate (DMAPP), and geranyl pyrophosphate (GPP). These pathways have the potential for better carbon and or energy efficiency than native pathways. Both decarboxylative and non-carboxylative condensations are utilized, enabling product synthesis from a number of different starting compounds. These condensation reactions serve as a platform for the synthesis of isoprenoid precursors when utilized in combination with a variety of metabolic pathways and enzymes for carbon rearrangement and the addition/removal of functional groups. Isoprenoid alcohols are key intermediary products for the production of isoprenoid precursors in these novel synthetic metabolic pathways.