(3S)-3-羟基-5-{[羟基(膦酰氧基)磷酰]氧基}-3-甲基戊酸 | 1492-08-6

• 分子结构分类: 有机化合物 - 有机氧化合物 - 有机含氧阴离子化合物
• 中文名称: (3S)-3-羟基-5-{[羟基(膦酰氧基)磷酰]氧基}-3-甲基戊酸
• 英文名称: mevalonic acid 5-diphosphate
• 英文别名: Mevalonsaeure-5-pyrophosphat；3-Hydroxy-5-pyrophosphonooxy-3-methyl-valeriansaeure；D,L-Mevalonsaeure-5-pyrophosphat；3-Hydroxy-5-[hydroxy(phosphonooxy)phosphoryl]oxy-3-methylpentanoic acid
• CAS: 1492-08-6
• 化学式: C₆H₁₄O₁₀P₂
• 分子量: 308.119
• InChiKey: SIGQQUBJQXSAMW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.2
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  171
• 氢给体数：
  5
• 氢受体数：
  10

安全信息

• 海关编码：
  2931900090

反应信息

• 作为反应物：
  描述：

  (3S)-3-羟基-5-{[羟基(膦酰氧基)磷酰]氧基}-3-甲基戊酸 在 (S_P)-adenosine 5'-O<3-thio<3-(17)O2,(18)O>>triphosphate 作用下， 生成 二磷酸 P-(3-甲基-3-丁烯-1-基)酯
  参考文献：
  名称：

  Frey, P. A.; Cardemil, E.; Iyengar, R., Phosphorus and Sulfur and the Related Elements, 1987, vol. 30, p. 563 - 566

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl 3-hydroxy-3-methyl-5-tosyloxypentanone 在 lithium hydroxide 、 tris(tetra-n-butylammonium) hydrogen pyrophosphate 作用下， 以 乙腈 为溶剂， 反应 22.0h， 生成 (3S)-3-羟基-5-{[羟基(膦酰氧基)磷酰]氧基}-3-甲基戊酸
  参考文献：
  名称：

  Bifunctional Inhibitors of Mevalonate Kinase and Mevalonate 5-Diphosphate Decarboxylase

  摘要：

  A bifunctional inhibitor of mevalonate kinase and mevalonate 5-diphosphate decarboxylase was synthesized. Both enzymes are in the cholesterol biosynthetic pathway and play an important role in regulating cholesterol biosynthesis. The molecule may become a useful lead compound for further development for treating cardiovascular disease and cancer. This study provides a novel example of a single inhibitor blocking two sequential steps simultaneously in the cholesterol biosynthetic pathway.

  DOI：

  10.1021/ol052573s

文献信息

• ß-Modified Phosphoric Acid Compound Precursor, ß-Modified Phosphoric Acid Compound, Reaction Inhibitor and Medicine Containing the Same, and Method for Inhibiting Reaction
  申请人：Japan Science and Technology Agency

  公开号：US20210284679A1

  公开（公告）日：2021-09-16

  A β-modified phosphoric acid compound precursor having a partial structure represented by where A 1 represents —SR 1 , —S—S—R 1 , —SeR 1 , or —X, where X is a halogen selected from fluorine, chlorine, bromine, and iodine; R 1 represents hydrogen, an alkyl group having 1 to 20 carbon atoms, or the like; L 1 represents hydrogen, an alkyl group having 1 to 20 carbon atoms, or the like; L 2 represents an alkyl group having 1 to 20 carbon atoms, or the like; L 1 and L 2 may be linked to each other to form a 4 to 6-membered ring structure; L 1 and L 2 may each have a substituent; and the symbol * represents a bond to be bonded to a phosphate group by phosphorylation. Further, provided are a reaction inhibitor and a medicine, each of which includes the β-modified phosphoric acid compound precursor.

  一种β-改性的磷酸化合物前体，具有以下部分结构：其中A1代表—SR1，—S—S—R1，—SeR1或—X，其中X是从氟、氯、溴和碘中选择的卤素；R1代表氢、具有1至20个碳原子的烷基或类似物；L1代表氢、具有1至20个碳原子的烷基或类似物；L2代表具有1至20个碳原子的烷基或类似物；L1和L2可以连接在一起形成4至6个成员的环状结构；L1和L2可以各自具有取代基；符号*表示通过磷酸化作用与磷酸基结合的键。此外，还提供了一种反应抑制剂和一种药物，其中每种药物均包括β-改性磷酸化合物前体。
• Process For The Production Of Isoprenol From Mevalonate Employing a Diphosphomevalonate Decarboxylae
  申请人：Global Bioenergies SA

  公开号：US20150376653A1

  公开（公告）日：2015-12-31

  Described is a method for the enzymatic production of isoprenol using mevalonate as a substrate and enzymatically converting it by a decarboxylation step into isoprenol as well as the use of an enzyme which is capable of catalyzing the decarboxylation of mevalonate for the production of isoprenol from mevalonate. Furthermore described is the use of mevalonate as a starting material for the production of isoprenol in an enzymatically catalysed reaction. Also disclosed is a method for the production of isoprene comprising the method for the production of isoprenol using mevalonate as a substrate and enzymatically converting it by a decarboxylation step into isoprenol and further comprising the step of converting the produced isoprenol into isoprene as well as a method for the production of isoamyl alcohol comprising the method for the production of isoprenol using mevalonate as a substrate and enzymatically converting it by a decarboxylation step into isoprenol and further comprising the step of converting the produced isoprenol into isoamyl alcohol.

  描述了一种利用甲酮酸作为底物进行酶生产异戊醇的方法，并通过脱羧步骤酶催化将其转化为异戊醇，以及使用一种能够催化甲酮酸脱羧的酶来生产异戊醇的方法。此外，描述了将甲酮酸作为起始原料，在酶催化反应中生产异戊醇的用途。还公开了一种生产异戊二烯的方法，包括使用甲酮酸作为底物进行酶生产异戊醇，并通过脱羧步骤将其转化为异戊醇，以及将所生产的异戊醇转化为异戊二烯的步骤，以及一种生产异戊醇的方法，其中使用甲酮酸作为底物进行酶生产异戊醇，并通过脱羧步骤将其转化为异戊醇，进一步包括将所生产的异戊醇转化为异戊醇的步骤，以及生产异戊醇的方法，其中使用甲酮酸作为底物进行酶生产异戊醇，并通过脱羧步骤将其转化为异戊醇，进一步包括将所生产的异戊醇转化为异戊醇的步骤。
• COMPOSITIONS AND METHODS FOR PRODUCING ISOPRENE FREE OF C5 HYDROCARBONS UNDER DECOUPLING CONDITIONS AND/OR SAFE OPERATING RANGES
  申请人：CALABRIA Anthony R.

  公开号：US20100048964A1

  公开（公告）日：2010-02-25

  The invention features methods for producing isoprene from cultured cells wherein the cells in the stationary phase. The invention also provides compositions that include these cultured cells and/or increased amount of isoprene. The invention also provides for systems that include a non-flammable concentration of isoprene in the gas phase. Additionally, the invention provides isoprene compositions, such as compositions with increased amount of isoprene or increased purity.

  这项发明涉及从培养细胞中生产异戊二烯的方法，其中细胞处于静止阶段。该发明还提供包括这些培养细胞和/或增加的异戊二烯量的组合物。该发明还提供包括气相中非易燃浓度的异戊二烯的系统。此外，该发明提供异戊二烯组合物，例如含有增加的异戊二烯量或增加纯度的组合物。
• CONVERSION OF PRENYL DERIVATIVES TO ISOPRENE
  申请人：MCAULIFFE Joseph C.

  公开号：US20100113846A1

  公开（公告）日：2010-05-06

  The present invention provides methods for producing derivatives from cultured cells. In addition, the present invention provides methods for conversion of prenyl deerivatives, obtained from biological or petrochemical sources, to isoprene by employing chemical or biological catalysts. The present invention also provides compositions that include the cultured cells or isoprene or prenyl derivatives produced there from.

  本发明提供了一种从培养细胞中生产衍生物的方法。此外，本发明提供了一种将从生物或石油化学来源获得的萜基衍生物转化为异戊二烯的方法，通过使用化学或生物催化剂。本发明还提供了包括培养细胞、异戊二烯或其衍生物的组合物。
• OXADIAZOLE AND PHENOL DERIVATIVES AS ANTIBACTERIAL AND/OR HERBICIDAL AGENTS
  申请人：BOARD OF TRUSTEES OF NORTHERN ILLINOIS UNIVERSITY

  公开号：US20180271098A1

  公开（公告）日：2018-09-27

  Antimicrobial resistance is rising at an alarming rate. The methylerythritol phosphate (MEP) pathway is a metabolic pathway that produces the isoprenoids isopentyl pyrophosphate (IPP) and dimethylallyl pyrophosphate (DMAPP). Notably, the MEP pathway is present in bacteria and not mammals, which made the enzymes of the MEP pathway attractive targets for discovering new anti-infective agents due to reduced chances of off-target interactions leading to side effects. The biophysical properties of 2-C-methyl-D-erythritol 4-phosphate cytidylyltransferase (IspD) and 4-diphosphocytidyl-2-C-methyl-D-erythritol kinase (IspE) were determined to aid discovery of novel inhibitors. Thermal shift screening was used as an initial filter to narrow down a library of compounds with thermal shifts greater than 1° C., which could indicate binding to the IspD and IspE enzymes. Follow-up studies were performed using isothermal titration calorimetry and enzymatic inhibition assays. Results from these studies have revealed compounds with high micromolar inhibition of both IspD from Escherichia coli and IspE from Burkholderia thailandensis . The hit compounds are used for future development of more potent IspD and IspE inhibitors.

  抗微生物药物耐药性正在以令人担忧的速度上升。 甲基赤霉酸磷酸(MEP)途径是一种产生异戊二烯醇磷酸丙酯（IPP）和二甲基磷酸丙酯（DMAPP）的代谢途径。 值得注意的是，MEP途径存在于细菌中而不在哺乳动物中，这使得MEP途径的酶成为发现新抗感染剂的有吸引力的靶点，因为减少了产生副作用的离靶相互作用的机会。 通过测定2-C-甲基-D-赤霉酸4-磷酸胞苷基转移酶（IspD）和4-二磷酸胞苷基-2-C-甲基-D-赤霉酸激酶（IspE）的生物物理特性，有助于发现新的抑制剂。 利用热位移筛选作为初始过滤器，缩小了具有大于1°C热位移的化合物库，这可能表明这些化合物与IspD和IspE酶结合。 随后使用等温滴定热量计和酶抑制测定进行了后续研究。 这些研究结果显示出对大肠杆菌IspD和泰国布氏杆菌IspE均具有高微摩尔抑制作用的化合物。 这些有效化合物将用于未来开发更有效的IspD和IspE抑制剂。