DL-异柠檬酸 | 147-99-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: DL-异柠檬酸
• 英文名称: DL-isocitrate
• 英文别名: isocitrate；Isocitrat；1-hydroxypropane-1,2,3-tricarboxylate
• CAS: 147-99-9；393-64-6；393-65-7；445-42-1
• 化学式: C₆H₅O₇
• 分子量: 189.101
• InChiKey: ODBLHEXUDAPZAU-UHFFFAOYSA-K

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  141
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  DL-异柠檬酸 在 isocitrate dehydrogenase 、 nicotinamide adenine dinucleotide phosphate 作用下， 以 phosphate buffer 为溶剂， 生成 2-氧代-戊二酸离子(2-)
  参考文献：
  名称：

  Photochemical Coenzyme Regeneration in an Enzymatically Active Optical Material

  摘要：

  The photoinduced electron transfer between immobilized thionine and the dinucleotide enzyme cofactors NADH and NADPH in a SiO2 sol-gel matrix is reported. The electron-transfer quenching of thionine luminescence is used to monitor the rate of NADPH oxidation. Using Stern-Volmer quenching curves, the quenching rates in the silica matrix are I to 2 orders of magnitude smaller than those in solution. The rate constants for oxidation of NADPH by thionine were measured to be 9.8(+/-2.9) x 10(-3) s(-1) in solution and 8.8(+/-1.0) x 10(-4) s(-1) in the gel. Within the silica matrix, the photoinduced oxidation of NADPH is combined with the enzymatic reaction of isocitrate dehydrogenase, which uses the oxidized cofactor, NADP(+), as an electron acceptor in the oxidation of isocitrate. The encapsulated isocitrate dehydrogenase is active with a Michaelis-Menten constant, K-M, of 3 muM and a k(cat) of 0.67 muM/s per mg(enzyme). Because optical sensors use NADPH fluorescence as an indicator of the presence and relative concentration of enzyme substrate, the successful demonstration of photoinduced regeneration of NADP(+) makes possible continuous monitoring by the family of dehydrogenase enzymes.

  DOI：

  10.1021/jp038051g
• 作为试剂：
  描述：

  溴甲烷 在 isocitrate dehydrogenase 、 nicotinamide adenine dinucleotide phosphate 、 DL-异柠檬酸 作用下， 以 aq. phosphate buffer 为溶剂， 反应 0.5h， 生成 聚合甲醛
  参考文献：
  名称：

  ALKANE OXIDATION BY MODIFIED HYDROXYLASES

  摘要：

  这项发明涉及改良的羟化酶。该发明还涉及表达这种改良的羟化酶的细胞以及通过将适当底物与这些细胞接触来生产羟基化烷烃的方法。

  公开号：

  US20160024482A1

文献信息

• Simultaneous Quantification of Metabolites Involved in Central Carbon and Energy Metabolism Using Reversed-Phase Liquid Chromatography−Mass Spectrometry and in Vitro ¹³C Labeling
  作者：Wen-Chu Yang、Miroslav Sedlak、Fred E. Regnier、Nathan Mosier、Nancy Ho、Jiri Adamec

  DOI：10.1021/ac801693c

  日期：2008.12.15

  Comprehensive analysis of intracellular metabolites is a critical component of elucidating cellular processes. Although the resolution and flexibility of reversed-phase liquid chromatography−mass spectrometry (RPLC−MS) makes it one of the most powerful analytical tools for metabolite analysis, the structural diversity of even the simplest metabolome provides a formidable analytical challenge. Here we describe a robust RPLC−MS method for identification and quantification of a diverse group of metabolites ranging from sugars, phosphosugars, and carboxylic acids to phosphocarboxylics acids, nucleotides, and coenzymes. This method is based on in vitro derivatization with a 13C-labeled tag that allows internal standard based quantification and enables separation of structural isomer pairs like glucose 6-phosphate and fructose 6-phosphate in a single chromatographic run. Calibration curves for individual metabolites showed linearity ranging over more than 2 orders of magnitude with correlation coefficients of R2 > 0.9975. The detection limits at a signal-to-noise ratio of 3 were below 1.0 μM (20 pmol) for most compounds. Thirty common metabolites involved in glycolysis, the pentose phosphate pathway, and tricarboxylic acid cycle were identified and quantified from yeast lysate with a relative standard deviation of less than 10%.

  详细分析细胞内代谢物是阐明细胞过程的关键组成部分。尽管反相液相色谱-质谱联用（RPLC-MS）的分辨率和灵活性使其成为代谢物分析中最强大的分析工具之一，但即使是简单的代谢组，其结构的多样性也带来了巨大的分析挑战。本文描述了一种稳健的RPLC-MS方法，用于鉴定和定量一系列广泛的代谢物，包括糖类、磷酸糖、羧酸、磷酸羧酸、核苷酸和辅酶。该方法基于使用13C标记标签的体外衍生化，允许基于内标的定量，并能在单次色谱运行中分离结构异构体对，如葡萄糖6-磷酸和果糖6-磷酸。单个代谢物的校准曲线显示线性范围超过两个数量级，相关系数R² > 0.9975。大多数化合物的信噪比为3的检测限低于1.0 μM（20 pmol）。从酵母裂解液中鉴定和定量了涉及糖酵解、戊糖磷酸途径和三羧酸循环的30种常见代谢物，相对标准偏差小于10%。
• Oxidation of compounds using genetically modified Candida
  申请人：Ness Jon E.

  公开号：US08597923B2

  公开（公告）日：2013-12-03

  A substantially pure Candida host cell is provided for the biotransformation of a substrate to a product wherein the host cell is characterized by a first genetic modification class that comprises one or more genetic modifications that collectively or individually disrupt at least one alcohol dehydrogenase gene in the substantially pure Candida host cell.

  提供了一种高度纯净的白色念珠菌宿主细胞，用于将底物生物转化为产物，其中该宿主细胞的特征是具有第一遗传修饰类别，该类别包括一个或多个遗传修饰，这些遗传修饰共同或单独地破坏了至少一个酒精脱氢酶基因在高度纯净的白色念珠菌宿主细胞中。
• OXIDATION OF COMPOUNDS USING GENETICALLY MODIFIED CANDIDA
  申请人：SYNTHEZYME LLC

  公开号：US20150218486A1

  公开（公告）日：2015-08-06

  An α-carboxyl-ω-hydroxyl fatty acid oxidized from a substantially pure Candida host cell, wherein the substantially pure Candida host cell is characterized by a first genetic modification class that comprises one or more genetic modifications that collectively or individually disrupt an alcohol dehydrogenase gene, and a second genetic modification class, wherein the second genetic modification class comprises an insertion of a first gene into the Candida host cell genome.

  一种从基本纯的Candida宿主细胞氧化的α-羧基-ω-羟基脂肪酸，其中基本纯的Candida宿主细胞的特征是具有第一遗传修饰类，该类包括一个或多个遗传修饰，这些修饰共同或个别地破坏了醇脱氢酶基因，以及第二遗传修饰类，其中第二遗传修饰类包括将第一基因插入到Candida宿主细胞基因组中。
• BIOTRANSFORMATION USING GENETICALLY MODIFIED CANDIDA
  申请人：Ness Jon E.

  公开号：US20150094483A1

  公开（公告）日：2015-04-02

  A substantially pure Candida host cell is provided for the biotransformation of a substrate to a product wherein the host cell is characterized by a first genetic modification class that comprises one or more genetic modifications that collectively or individually disrupt at least one alcohol dehydrogenase gene in the substantially pure Candida host cell.

  提供了一种基本纯净的Candida宿主细胞，用于将底物生物转化为产物，其中该宿主细胞的特征是具有第一遗传修饰类别，该类别包括一个或多个遗传修饰，这些修饰共同或单独破坏了至少一个酒精脱氢酶基因在基本纯净的Candida宿主细胞中。
• Biotransformation using genetically modified Candida
  申请人：SyntheZyme, LLC

  公开号：US09359581B2

  公开（公告）日：2016-06-07

  A substantially pure Candida host cell is provided for the biotransformation of a substrate to a product wherein the host cell is characterized by a first genetic modification class that comprises one or more genetic modifications that collectively or individually disrupt at least one alcohol dehydrogenase gene in the substantially pure Candida host cell.

  提供了一种高度纯净的白色念珠菌宿主细胞，用于将底物生物转化为产物，其中该宿主细胞的特征是具有第一遗传修饰类别，该类别包括一种或多种遗传修饰，这些修饰共同或单独破坏了至少一个酒精脱氢酶基因在高度纯净的白色念珠菌宿主细胞中。