dimethyl α-hydroxyglutarate | 81077-10-3

• 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: dimethyl α-hydroxyglutarate
• 英文别名: Dimethyl 2-hydroxypentanedioate
• CAS: 81077-10-3
• 化学式: C₇H₁₂O₅
• 分子量: 176.169
• InChiKey: SHBLBMNYOOCEFM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  dimethyl α-hydroxyglutarate 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 以55%的产率得到5-氧代四氢呋喃-2-羧酸甲酯
  参考文献：
  名称：

  Enantiomerically pure tetrahydro-5-oxo-2-furancarboxylic esters from dialkyl 2-oxoglutarates

  摘要：

  Enantiomerically pure tetrahydro-5-oxo-2-furancarboxylic esters can be prepared either by enzymatic resolution of the racemic gamma-lactones themselves or by bioreduction with baker's yeast of dialkyl 2-oxoglutarates and subsequent cyclization of the resulting dialkyl 2-hydroxyglutarates. The best results were obtained by the former route, by which the desired compounds were isolated in high enantiomeric excess. Bioreductions were less satisfactory. In fact the hydroxyester intermediates were initially formed as racemic mixtures and their final enantiomeric enrichment was reached by asymmetric destruction, occurring in the bioreaction medium, however at the same time large amounts of alkyl 4-hydroxybutanoates were formed as side products. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00286-4
• 作为产物：
  描述：

  alpha-酮戊二酸 在 sodium tetrahydroborate 、 硫酸 作用下， 以 甲醇 为溶剂， 生成 dimethyl α-hydroxyglutarate
  参考文献：
  名称：

  发酵过程中Mercurialis perennis L.的水提物中的苷和生物碱成分的代谢命运。

  摘要：

  狗的汞（Mercurialis perennis L.）是一种古老的药用植物，如今已​​用于补充药物。该植物的水发酵提取物主要用于治疗外部炎症的方法，但仍缺乏全面的植物化学特征。因此，研究了在发酵和贮藏过程中从多年生红孢菌提取物中特征化合物类别的转化。两种主要的近邻相（=（2R）-O-[（E）-咖啡酰]苹果酸; 1）和巯基酸（=（2R）-[（E）-咖啡酰氧基]戊二酸; 2通过HPLC-DAD监测）。降解遵循二级动力学，两种成分的半衰期计算值分别为67和30个月。衍生化后，通过GC / MS在AcOEt提取物中检测到几种深度代谢产物，为（t）BuMe2 Si（TBDMS）衍生物，主要是二氢肉桂酸。此外，发现了许多α-羟基酸，据称它们是氨基酸或肽的降解产物。还检查了主要生物碱hermidin的微生物变化。发酵三天后，形成了三种新型的N-代谢物，并通过GC / MS和NMR方法将它们分别以3-乙

  DOI：

  10.1002/cbdv.201200424

文献信息

• [EN] METHODS OF TREATING DISEASE BY METABOLIC CONTROL OF T-CELL DIFFERENTIATION<br/>[FR] MÉTHODES DE TRAITEMENT DE MALADIES PAR LA RÉGULATION MÉTABOLIQUE DE LA DIFFÉRENCIATION DES LYMPHOCYTES T
  申请人：THE J DAVID GLADSTONE INST

  公开号：WO2017123808A1

  公开（公告）日：2017-07-20

  Provided herein are methods for treating an individual for a disease (e.g., an autoimmune disease or a cancer) using an active agent which affects metabolism of α-ketoglutarate (α-KG) and/or 2-hydroxyglutarate (2-HG) in differentiating T cells. In some embodiments, a Got1 inhibitor is used to generate a population of T cells enriched in peripheral regulatory T (iTreg) cells, which population enriched in iTreg cells may find use in treating an autoimmune disease. In some embodiments, a TCA cycle-associated metabolite, or a derivative thereof, is used to generate a population of T cells in enriched in IL-17- and IL-17F-producing CD4 T (TH17) cells, which population enriched in TH17 cells may find use in treating a cancer.

  本文提供了一种治疗个体患病（例如自身免疫疾病或癌症）的方法，使用影响α-酮戊二酸（α-KG）和/或2-羟基戊二酸（2-HG）在分化T细胞中代谢的活性剂。在某些实施例中，使用Got1抑制剂生成富集于外周调节性T细胞（iTreg）细胞的T细胞群，这种富集于iTreg细胞的群体可用于治疗自身免疫疾病。在某些实施例中，使用TCA循环相关代谢物或其衍生物生成富含IL-17和IL-17F产生的CD4 T（TH17）细胞的T细胞群，这种富含TH17细胞的群体可用于治疗癌症。
• [EN] TRIAZOLE CONJUGATED UREAS, THIOUREAS, CARBAMATES, AND "REVERSED" CARBAMATES FOR PSMA-TARGETED IMAGING AGENTS AND USES THEREOF<br/>[FR] URÉES, THIOURÉES, CARBAMATES ET CABARMATES « INVERSÉS » CONJUGUÉS À DU TRIAZOLE, POUR AGENTS D'IMAGERIE CIBLANT L'ANTIGÈNE PSMA ET LEURS UTILISATIONS
  申请人：UNIV JOHNS HOPKINS

  公开号：WO2017027870A1

  公开（公告）日：2017-02-16

  Triazole conjugated urea-based and thiourea-based scaffolds that have high binding affinity to PSMA are disclosed. These scaffolds can be radiolabeled and used to image cells and tumors that express PSMA. Methods of synthesizing radiofluorinated triazole conjugated urea-based and thiourea-based scaffolds also are disclosed.

  本文披露了具有高结合亲和力的与PSMA结合的三唑基脲和硫脲基脚手架。这些脚手架可以被放射标记，并用于成像表达PSMA的细胞和肿瘤。同时还披露了合成放射性氟三唑基脲和硫脲基脚手架的方法。
• Tunable System for Electrochemical Reduction of Ketones and Phthalimides
  作者：Yaxin Wang、Jianyou Zhao、Tianjiao Qiao、Jian Zhang、Gong Chen

  DOI：10.1002/cjoc.202100508

  日期：2021.12

  Herein, we report an efficient, tunable system for electrochemical reduction of ketones and phthalimides at room temperature without the need for stoichiometric external reductants. By utilizing NaN3 as the electrolyte and graphite felt as both the cathode and the anode, we were able to selectively reduce the carbonyl groups of the substrates to alcohols, pinacols, or methylene groups by judiciously

  在此，我们报告了一种高效、可调的系统，用于在室温下电化学还原酮和邻苯二甲酰亚胺，无需化学计量的外部还原剂。通过使用 NaN 3作为电解质和石墨毡作为阴极和阳极，我们能够通过明智地选择溶剂和酸性添加剂，将基材的羰基选择性地还原为醇、频哪醇或亚甲基。反应条件与多种官能团兼容，邻苯二甲酰亚胺可以进行一锅还原环化反应，得到带有吲哚里西啶支架的产物。机理研究表明，反应涉及电子、质子和氢原子的转移。重要的是，N 3 /HN 3 循环作为氢原子穿梭运行，这对于将羰基还原为亚甲基至关重要。
• Metal-catalyzed reductive deamination of glutamic acid to bio-based dimethyl glutarate and methylamines
  作者：Free De Schouwer、Thomas Cuypers、Laurens Claes、Dirk E. De Vos

  DOI：10.1039/c6gc03222b

  日期：——

  Glutamic acid is a promising renewable platform molecule which is abundantly available in biomass waste streams; it is also efficiently manufactured by fermentation. Here we report the reductive deamination of...

  谷氨酸是一种有前途的可再生平台分子，可在生物质废物流中大量使用。它也可以通过发酵有效地制造。在这里，我们报告...的还原性脱氨作用。
• Differentiation of 2‐hydroxyglutarate enantiomers and its lactones by gas chromatography/electron ionization tandem mass spectrometry
  作者：Shinji K. Strain、Morris D. Groves、Mark R. Emmett

  DOI：10.1002/rcm.8485

  日期：2019.9.15

  2‐Hydroxyglutarate (2‐hg) exists as enantiomers and can readily undergo cyclization to its lactone. Gas chromatography/electron ionization mass spectrometry (GC/EI‐MS) has been used to separate 2‐hg enantiomers in bodily fluids but the assay cannot simultaneously measure cyclic and acylic 2‐hg enantiomers. Furthermore, the assignment of ion structures was not verified by complementary MS data.

  2-羟基戊二酸酯（2-hg）以对映异构体的形式存在，可以很容易地环化成其内酯。气相色谱/电子电离质谱（GC / EI-MS）已用于分离体液中的2-hg对映异构体，但该测定法无法同时测量环状和酰基2-hg对映异构体。此外，补充的MS数据未验证离子结构的分配。