乳酸盐 | 113-21-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 乳酸盐
• 中文别名: 乳酸
• 英文名称: lactate anion
• 英文别名: lactate；DL-lactate；lactate ion；Lac；methyl-2-hydroxyethanoate；2-hydroxypropanoate
• CAS: 113-21-3
• 化学式: C₃H₅O₃
• 分子量: 89.0709
• InChiKey: JVTAAEKCZFNVCJ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  6
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  60.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乳酸盐 在 水 作用下， 生成 乙酸盐
  参考文献：
  名称：

  Modeling the Production of and Competition for Hydrogen in a Dechlorinating Culture

  摘要：

  A comprehensive biokinetic model employing Michaelis-Menten-type kinetics, H(2) thresholds, and thermodynamic limitations oh donor fermentation was used to describe both fermentation of electron donors and competition for the evolved H(2) between hydrogenotrophic tetrachloroethane dechlorinators and methanogens. Model simulations compared favorably to experimental data where delivery of H(2) to a tetrachloroethene dechlorinator was accomplished using the donors butyric acid, ethanol, lactic acid, and propionic acid. Fermentations of the different donors were characterized by different dynamic patterns, of H(2) generation that were captured successfully by the model. Experimental data and model simulations show that the ability to use H(2) at appreciable rates at low levels provides a competitive advantage to dechlorinators over methanogens. Slowly fermented substrates producing lower H(2) levels-kinetically accessible to dechlorinators, but too low for significant use by methanogenic competitors-were more effective and persistent "selective" stimulators of dechlorination than rapidly fermented substrates producing higher Ha levels-accessible to both dechlorinators and methanogens. Model simulations suggest that adding excessive levels of rapidly fermented, high H(2)-level-generating donors in an attempt to overcome competition, instead results in a dominant methanogen population and an eventual failure of dechlorination. When stimulating dechlorination, the quality of the donor as well as; the quantity added must be considered.

  DOI：

  10.1021/es980136l
• 作为产物：
  描述：

  丙酮醛 在 deglycase-1 作用下， 生成 乳酸盐
  参考文献：
  名称：

  The C terminus of DJ-1 determines its homodimerization, MGO detoxification activity and suppression of ferroptosis

  摘要：

  DJ-1 是一种与癌症和常染色体早发帕金森病有关的多功能蛋白质。除了已被证实的抗氧化活性外，最近的研究表明 DJ-1 还具有降解酶活性和抗肥胖作用。有研究表明，DJ-1 形成的同源二聚体决定了其抗氧化应激活性。本研究探讨了 DJ-1 的二聚体结构与其新报道的活性之间的关系。在Flag标记和Myc标记的DJ-1过表达的HEK293T细胞中，我们进行了缺失突变和点突变，缩小了C末端最关键基团的范围。我们发现，DJ-1 C末端最后三个氨基酸（DJ-1 δC3）的缺失突变破坏了它的同源二聚化，其中疏水的L187残基对DJ-1的同源二聚化非常重要。此外，与野生型DJ-1（DJ-1 WT）相比，DJ-1 δC3突变体和点突变体L187E的甲基乙二醛（MGO）解毒和脱糖能力几乎丧失。我们还发现，δC3 和 L187E 对 DJ-1â/â 小鼠胚胎成纤维细胞中麦拉宁诱导的铁突变的抑制作用被取消，但 V51C 的抑制作用部分减弱。因此，我们的研究结果表明，DJ-1的C末端对其同二聚体化、降解活性和抑制铁卟啉沉着至关重要。

  DOI：

  10.1038/s41401-020-00531-1

文献信息

• L-2-Hydroxyglutarate production arises from noncanonical enzyme function at acidic pH
  作者：Andrew M Intlekofer、Bo Wang、Hui Liu、Hardik Shah、Carlos Carmona-Fontaine、Ariën S Rustenburg、Salah Salah、M R Gunner、John D Chodera、Justin R Cross、Craig B Thompson

  DOI：10.1038/nchembio.2307

  日期：2017.5

  Acidification enhances lactate dehydrogenase– and malate dehydrogenase–mediated promiscuous production of L-2-hydroxyglutarate (L-2HG) from α-ketoglutarate and stabilizes HIF-1α levels. The metabolite 2-hydroxyglutarate (2HG) can be produced as either a D- R- or L- S- enantiomer, each of which inhibits α-ketoglutarate (αKG)-dependent enzymes involved in diverse biologic processes. Oncogenic mutations in isocitrate dehydrogenase (IDH) produce D-2HG, which causes a pathologic blockade in cell differentiation. On the other hand, oxygen limitation leads to accumulation of L-2HG, which can facilitate physiologic adaptation to hypoxic stress in both normal and malignant cells. Here we demonstrate that purified lactate dehydrogenase (LDH) and malate dehydrogenase (MDH) catalyze stereospecific production of L-2HG via 'promiscuous' reduction of the alternative substrate αKG. Acidic pH enhances production of L-2HG by promoting a protonated form of αKG that binds to a key residue in the substrate-binding pocket of LDHA. Acid-enhanced production of L-2HG leads to stabilization of hypoxia-inducible factor 1 alpha (HIF-1α) in normoxia. These findings offer insights into mechanisms whereby microenvironmental factors influence production of metabolites that alter cell fate and function.

  酸化作用增强乳酸脱氢酶和苹果酸脱氢酶介导的从α-酮戊二酸产生L-2-羟基戊二酸（L-2HG）的非特异性反应，并稳定HIF-1α水平。代谢物2-羟基戊二酸（2HG）可以作为D-R-或L-S-手性异构体产生，每种都能抑制涉及多种生物过程的α-酮戊二酸（αKG）依赖性酶。异柠檬酸脱氢酶（IDH）的致癌突变产生D-2HG，导致细胞分化的病理阻断。另一方面，氧气限制导致L-2HG积累，这可以促进正常细胞和恶性细胞对低氧应激的生理适应。在此，我们证明纯化的乳酸脱氢酶（LDH）和苹果酸脱氢酶（MDH）通过非特异性还原替代底物αKG，催化特异性产生L-2HG。酸性pH通过促进αKG的质子化形式，该形式结合到LDHA的底物结合口袋中的关键残基，从而增强L-2HG的产生。酸增强的L-2HG产生导致在常氧条件下稳定缺氧诱导因子1α（HIF-1α）。这些发现提供了关于微环境因素如何影响代谢物产生，从而改变细胞命运和功能的机制的见解。
• Efficient transfer hydrogenation of carbonate salts from glycerol using water-soluble iridium N-heterocyclic carbene catalysts
  作者：Diana Ainembabazi、Kai Wang、Matthew Finn、James Ridenour、Adelina Voutchkova-Kostal

  DOI：10.1039/d0gc01958e

  日期：——

  catalysts for carbonate transfer hydrogenation from glycerol, requiring no additives in aqueous media. The most prolific catalyst of the nine examined, [Ir(NHC-Ph-SO3−)2CO2]Na (cat 7), effectively facilitates the reaction at low catalyst loading (10 ppm) at 150 °C using microwave or conventional heating. The cation of the carbonate salt significantly impacts catalytic activity, with highest activity

  从生物质衍生的醇（如甘油）转移CO 2和碳酸盐进行氢化，以生成甲酸和乳酸，这是使两种废物流均价化的极具吸引力的途径，并且比直接进行碳酸盐加氢在热力学上更为有利。在此方法的第一个均相催化剂的开创性报告的基础上，我们扩展了具有磺酸盐官能化的翼尖的耐热且水溶性的Ir（I）和Ir（III）N-杂环卡宾（NHC）配合物以及用于碳酸酯从甘油转移加氢的稳健催化剂，在水性介质中无需任何添加剂。九个最多产的催化剂检查，物[Ir（NHC-PH-SO 3 - ）2使用微波或常规加热，CO 2 ] Na（催化剂7）可有效地促进在150°C的低催化剂负载量（10 ppm）下的反应。碳酸盐的阳离子显着影响催化活性，在Cs 2 CO 3中观察到最高的活性（乳酸和甲酸在6小时内分别为27 850和13 350 TON，而K 2 CO 3则为15 400和8120 ）。发现催化量的Cs +可显着增强K 2 CO 3的活性。在N
• Selective Transformation of Vicinal Glycols to α-Hydroxy Acetates in Water via a Dehydrogenation and Oxidization Relay Process by a Self-Supported Single-Site Iridium Catalyst
  作者：Lingyun Shen、Zhe-Ning Chen、Qingshu Zheng、Jiajie Wu、Xin Xu、Tao Tu

  DOI：10.1021/acscatal.1c04354

  日期：2021.11.5

  and biodegradable polymers, but their conventional syntheses are usually restricted to aromatic substrates, especially, in a stepwise manner. Herein, we disclose the transformation of alkyl and aryl vicinal glycols to α-hydroxy acetates in water under the air atmosphere with our solid self-supported NHC-Ir single-site catalyst. Both aliphatic and aromatic glycols are compatible with a much higher catalytic

  α-羟基酸因其广泛存在于生物活性分子和可生物降解聚合物中而引起了广泛关注，但它们的常规合成通常仅限于芳香族底物，尤其是逐步合成的。在此，我们公开了使用我们的固体自支撑 NHC-Ir 单中心催化剂在空气气氛下将烷基和芳基邻二醇转化为 α-羟基乙酸酯。由于“隔离效应”，在这种固体单中心催化剂存在下，脂肪族和芳香族二醇都具有比其他可行的分子催化剂（93% 对 <35%）高得多的催化效率。值得注意的是，我们的催化剂可以重复使用 20 次，而催化活性和选择性没有明显损失。控制实验和密度泛函理论计算表明，该反应首先进行催化剂促进的脱氢，然后通过空气中的氧气进行意想不到的氧化中继步骤，导致形成 α-羟基乙酸盐。我们的协议可能有助于提高现成且廉价的二醇的价值。
• Photo-production of lactate from glyoxylate: how minerals can facilitate energy storage in a prebiotic world
  作者：Marcelo I. Guzman、Scot T. Martin

  DOI：10.1039/b924179e

  日期：——

  The reaction of glyoxylate with carbon dioxide to produce lactate is promoted when zinc sulfide is irradiated by ultraviolet light. These results, representing a model for the action of colloidal mineral semiconductors on early Earth, complete a consecutive series that culminates in entry-point molecules of the reductive tricarboxylic acid cycle.

  当用紫外光照射硫化锌时，促进了乙醛酸酯与二氧化碳反应生成乳酸酯。这些结果代表了胶态矿物半导体在地球早期的作用模型，完成了一个连续的系列，最终形成了还原性三羧酸循环的入口点分子。
• Selective Access to All Four Diastereomers of a 1,3-Amino Alcohol by Combination of a Keto Reductase- and an Amine Transaminase-Catalysed Reaction
  作者：Hannes Kohls、Mattias Anderson、Jonathan Dickerhoff、Klaus Weisz、Armando Córdova、Per Berglund、Henrike Brundiek、Uwe T. Bornscheuer、Matthias Höhne

  DOI：10.1002/adsc.201500214

  日期：2015.5.26

  asymmetric synthesis of functionalised amines bearing more than one stereocentre, such as 1,3‐amino alcohols, remains challenging. By employing a keto reductase (KRED) and two enantiocomplementary amine transaminases (ATA), we developed a biocatalytic route towards all four diastereomers of 4‐amino‐1‐phenylpentane‐2‐ol as a representative molecule bearing the 1,3‐amino alcohol functionality. Starting from a

  手性胺的生物催化合成已成为化学家工具箱的宝贵补充。但是，带有一个以上立体中心的官能化胺（例如1,3-氨基醇）的有效不对称合成仍然具有挑战性。通过使用酮还原酶（KRED）和两种对映体互补胺转氨酶（ATA），我们开发了一种生物催化途径，可将4个氨基-1-苯基戊烷-2-醇的所有四个非对映异构体作为带有1,3-氨基醇的代表性分子功能。从外消旋羟基酮开始，使用（S）选择性KRED的动力学拆分提供了光学活性羟基酮（86％ee）和相应的二酮。羟基酮的进一步转氨反应可通过（R）或（S）选择性ATA，得到（2 R，4 R）-和（2 R，4 S）-1,3-氨基醇非对映异构体。其余两个非对映异构体可在随后的两个不对称步骤中获得：相同的KRED使二酮在区域和对映异构体上还原，生成（S）-构型的羟基酮。最终，随后用（R）-和（S）-选择性ATA进行的粗产物转氨作用分别产生了其余的（2 S，4 R）-和（2 S，4 S）-非对映异构体。