pimelate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: pimelate
• 英文别名: Heptanedioate
• 化学式: C₇H₁₀O₄
• 分子量: 158.154
• InChiKey: WLJVNTCWHIRURA-UHFFFAOYSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  molybdenum;sulfane;dihydrate 、 pimelate 以 甲醇 、 水 为溶剂， 生成 [Mo12O12S12(hydroxo)12(pimelate)](2-)
  参考文献：
  名称：

  “Wheeling Templates” in Molecular Oxothiomolybdate Rings: Syntheses, Structures, and Dynamics

  摘要：

  The influence of three dicarboxylate anions, oxalate, (C2O4)(2-), glutarate, (H6C5O4)(2-), and pimelate, (H10C7O4)(2-), on the self-condensation process of the [Mo2S2O2](2+) dithiocation has been investigated. [Mo8S8O8(OH)(8)(C2O4)](2-) ([Mo-8-ox](2-)), [Mo10S10O10(OH)(10)(H6C5O4)](2-) ([Mo-10-glu](2-)), and [Mo12S12O12(OH)(12)(MoC2O4)](2-) ([Mo-12-pim](2-)) have been prepared and characterized in aqueous solution by H-1 NMR and electrospray mass spectroscopy and in the solid state by elemental analyses, X-ray crystallography, and infrared spectroscopy. The molecular arrangement of [Mo-8-ox](2-), [Mo-10-glu](2-), and [Mo-12-pim](2-) exhibits the same type of topology derived from the neutral cyclic {Mo-2n,S-2n,O-2n,(OH)(2n)} backbone. {Mo2nS2nO2n(OH)(2n)} inorganic rings encapsulate the organic guest with direct covalent interactions between Mo centers and carboxylate groups. Excess of glutarate does not change the molecular arrangement of the anion but modifies the solid-state arrangement of [Mo-10-glu](2-). Rb-4(C5H6O4)[Mo10S10O10(OH)(10)(H6C5O4)]. 5H(2)O (Rb(4)glu[Mo-10-glu]. 5H(2)O) has been crystallized and structurally characterized by X-ray diffraction. The structure of Rb(4)glu[Mo-10-glu]. 5H(2)O contains the same decameric molecular anion as that found in Cs-2[Mo-10-glu]. 20H(2)O with an additional glutarate capping the molecular wheel. The supramolecular interactions developed in Rb(4)glu[Mo-10-glu]. 5H(2)O are ensured by hydrogen bonds involving the hydroxo bridges of the inorganic ring and the carboxylate groups of the additional glutarate. Negative-ion electrospray mass spectroscopy (ESMS) has been performed on aqueous solution containing the {Mo2S2O2} building block and the templating agent at pH 4.5. The anions [Mo-8-ox](2-), [Mo-10-glu](2-), and [Mo-12-pim](2-) were clearly identified by their parent peaks observed in the ESMS spectra. Experimental mit ratios are fully consistent with the corresponding X-ray diffraction results.The templated anionic Mo-2n rings have been characterized by H-1 NMR spectroscopy in aqueous solution and in acetonitrile-d(3) The H-1 NMR spectra of [Mo-8-ox](2-), [Mo-10-glu](2-), and [Mo-12-pim](2-) as Li+ salts in CD3CN unambiguously contain the resonances of the hydroxo bridges belonging to the ring and those of the inner CH2 groups of the alkyl chain in [Mo-10-glu](2-) and [Mo-12-pim](2-). Variable-temperature H-1 NMR spectra recorded in CD3CN revealed the fluxionality of [Mo-10-glu](2-) and [Mo-12-pim](2-) in contrast to the rigidity of [Mo-8-ox](2-). At low temperature (T = 226 K), the motion of the guest, i.e., the central template in Mo-10 and Mo-12 rings, becomes slow enough on the NMR time scale to postulate the presence of conformational isomers in solution.

  DOI：

  10.1021/ja001878t
• 作为产物：
  描述：

  环庚醇 在 水 、 sodium hydroxide 作用下， 以25%的产率得到pimelate
  参考文献：
  名称：

  电气化己二酸生产：铜促进环己醇的氧化和 C−C 裂解

  摘要：

  通过将铜掺入氢氧化镍电极，实现了将环己醇高效电催化氧化为己二酸。Cu 2+在削弱表面吸附的以O为中心的自由基与NiOOH表面之间的相互作用从而促进CC裂解方面起着关键作用。

  DOI：

  10.1002/anie.202214977

文献信息

• Synthesis, structure, spectral characteristic and photocatalytic degradation of organic dyes of a copper metal-organic framework based on tri(triazole) and pimelate
  作者：Lin-Lu Qian、Zhi-Xiang Wang、Li-Ming Zhu、Ke Li、Bao-Long Li、Bing Wu

  DOI：10.1016/j.saa.2019.02.059

  日期：2019.5

  A copper(II) metal-organic framework [Cu(ttpa)(pim)]·H2O}n (1) was synthesized and characterized by EA, IR, X-ray powder diffraction, optical band gaps, VB XPS spectra and luminescence (ttpa = tris(4-(1,2,4-triazol-1-yl)phenyl)amine, pim = pimelate). 1 exhibits the 3D pcu topology containing the [Cu2(COO)4] dimer building block. Eg, Ev and Ec of 1 were 2.37, 1.64 and −0.73 eV, respectively. MOF 1

  合成了铜（II）金属-有机骨架[Cu（ttpa）（pim）]·H 2 O} n（1）并通过EA，IR，X射线粉末衍射，光学带隙，VB XPS光谱进行了表征和发光（ttpa =三（4-（1,2,4-三唑-1-基）苯基）胺，pim =庚二酸酯）。图1展示了包含[Cu 2（COO）4 ]二聚体构件的3D pcu拓扑。E g，E v和E c为1，分别为2.37、1.64和-0.73 eV。MOF 1对可见光照射的亚甲基蓝和若丹明B的降解表现出很高的光催化效率。光催化剂1经过光催化实验后非常稳定，可以重复使用至少五次。在羟基自由基清除剂甘露醇和捕集剂1，4-苯二甲酸的存在下，通过光催化反应详细地假定并证实了光催化机理。
• Investigation of the first step of biotin biosynthesis in <i>Bacillus sphaericus</i>. Purification and characterization of the pimeloyl-CoA synthase, and uptake of pimelate
  作者：O Ploux、P Soularue、A Marquet、R Gloeckler、Y Lemoine

  DOI：10.1042/bj2870685

  日期：1992.11.1

  The pimeloyl-CoA synthase from Bacillus sphaericus has been purified to homogeneity from an overproducing strain of Escherichia coli. The purification yielded milligram quantities of the synthase with a specific activity of 1 unit/mg of protein. Analysis of the products showed that this enzyme catalysed the transformation of pimelate into pimeloyl-CoA with concomitant hydrolysis of ATP to AMP. Using a continuous spectrophotometric assay, we have examined the catalytic properties of the pure enzyme. The pH profile under Vmax. conditions showed a maximum around 8.5. Apparent Km values for pimelate, CoASH, ATP. Mg2- and Mg2+ were respectively 145 microM, 33 microM, 170 microM and 2.3 mM. The enzyme was inhibited by Mg2+ above 10 mM. This acid-CoA ligase exhibited a very sharp substrate specificity, e.g. neither GTP nor pimelate analogues (di- or mono-carboxylic acids) were processed. The bivalent metal ion requirement was also investigated: Mn2+ (73%) and Co2+ (32%) but not Ca2+ could replace Mg2+. The enzyme was inhibited by metal chelators such as 1,10-phenanthroline and EDTA. The synthase was a homodimer with a 28,000-M(r) subunit. N-Terminal sequencing definitely proved that this enzyme was encoded by the bioW gene. A careful study of pimelate uptake by B. sphaericus, E. coli and Pseudomonas dentrificans showed that this metabolite crossed the membrane of these microorganisms by passive diffusion, ruling out the involvement of the bioX gene product as pimelate carrier.

  来自球形芽孢杆菌的戊二酰辅酶A合酶已从大肠杆菌过度生产的菌株中纯化至同质性。纯化得到的合酶产量为毫克级，比活性为1单位/毫克蛋白质。产物分析表明，该酶催化戊二酸转化为戊二酰辅酶A，同时水解ATP为AMP。使用连续分光光度法，我们研究了纯酶的催化特性。在Vmax条件下的pH值曲线显示最大值约为8.5。戊二酸、辅酰辅酶A、ATP、Mg2+和Mg2+的表观Km值分别为145微米、33微米、170微米和2.3毫米。该酶在Mg2+浓度高于10毫摩尔时被抑制。该酸-CoA连接酶表现出非常尖锐的底物特异性，例如既不处理GTP也不处理戊二酸类似物（二元或单元羧酸）。双价金属离子需求也被研究：Mn2+（73％）和Co2+（32％）但不是Ca2+可以取代Mg2+。该酶被金属螯合剂如1,10-邻菲啰啉和EDTA抑制。合酶是一个具有28,000-M(r)亚基的同源二聚体。N末端测序明确证明该酶是由bioW基因编码的。对球形芽孢杆菌、大肠杆菌和铜绿假单胞菌的戊二酸摄取进行了仔细研究，结果表明，这种代谢产物通过被动扩散穿过这些微生物的细胞膜，排除了bioX基因产物作为戊二酸载体的可能性。
• Using the pimeloyl-CoA synthetase adenylation fold to synthesize fatty acid thioesters
  作者：Menglu Wang、Lucile Moynié、Peter J Harrison、Van Kelly、Andrew Piper、James H Naismith、Dominic J Campopiano

  DOI：10.1038/nchembio.2361

  日期：2017.6

  Biotin is an essential vitamin in plants and mammals, functioning as the carbon dioxide carrier within central lipid metabolism. Bacterial pimeloyl-CoA synthetase (BioW) acts as a highly specific substrate-selection gate, ensuring the integrity of the carbon chain in biotin synthesis. BioW catalyzes the condensation of pimelic acid (C7 dicarboxylic acid) with CoASH in an ATP-dependent manner to form

  生物素是植物和哺乳动物中必不可少的维生素，在中央脂质代谢中起二氧化碳载体的作用。细菌庚二酰辅酶A合成酶（BioW）充当高度特异性的底物选择门，可确保生物素合成中碳链的完整性。BioW以依赖于ATP的方式催化庚二酸（C7二羧酸）与CoASH的缩合反应，形成庚二酰-CoA，这是第一个专门的生物素构建基。枯草芽孢杆菌BioW的多种结构共同捕获了所有三种底物，中间庚二酰-腺苷酸酯和焦磷酸产物（PP i），表明该酶使用内部标尺来选择正确的二羧酸底物。腺苷酸中间体的催化机理和令人惊讶的稳定性都通过定点诱变得到了合理化。基于这种理解，BioW经过精心设计，可以合成高价值的庚酰基（C7）和辛酰基（C8）单羧酸-CoA和C8二羧酸-CoA产品，突出了该酶的合成潜力。