乳酸 | 311-80-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 乳酸
• 英文名称: D-lactate
• 英文别名: lactate；L-lactate；(2R)-2-hydroxypropanoate
• CAS: 311-80-8
• 化学式: C₃H₅O₃
• 分子量: 89.0709
• InChiKey: JVTAAEKCZFNVCJ-UWTATZPHSA-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 在 2,6-二氯靛酚 、 human D-2-hydroxyglutarate dehydrogenase 、 sodium chloride 作用下， 以 aq. buffer 为溶剂， 生成 piruvate
  参考文献：
  名称：

  Biochemical characterization of human D-2-hydroxyglutarate dehydrogenase and two disease related variants reveals the molecular cause of D-2-hydroxyglutaric aciduria

  摘要：

  D-2-hydroxyglutaric aciduria is a neurometabolic disorder, characterized by the accumulation of D-2-hydroxyglutarate (D-2HG) in human mitochondria. Increased levels of D-2HG are detected in humans exhibiting point mutations in the genes encoding isocitrate dehydrogenase, citrate carrier, the electron transferring flavoprotein (ETF) and its downstream electron acceptor ETF-ubiquinone oxidoreductase or D-2-hydroxyglutarate dehydrogenase (hD2HGDH). However, while the pathogenicity of several amino acid replacements in the former four proteins has been studied extensively, not much is known about the effect of certain point mutations on the biochemical properties of hD2HGDH.Therefore, we recombinantly produced wild type hD2HGDH as well as two recently identified disease-related variants (hD2HGDH-I147S and -V444A) and performed their detailed biochemical characterization. We could show that hD2HGDH is a FAD dependent protein, which is able to catalyze the oxidation of D-2HG and D-lactate to alpha-ketoglutarate and pyruvate, respectively. The two variants were obtained as apo-proteins and were thus catalytically inactive. The addition of FAD failed to restore enzymatic activity of the variants, indicating that the cofactor binding site is compromised by the single amino acid replacements. Further analyses revealed that both variants form aggregates that are apparently unable to bind the FAD cofactor.Since, D-2-hydroxyglutaric aciduria may also result from a loss of function of either the ETF or its downstream electron acceptor ETF-ubiquinone oxidoreductase, ETF may serve as the cognate electron acceptor of reduced hD2HGDH. Here, we show that hD2HGDH directly reduces recombinant human ETF, thus establishing a metabolic link between the oxidation of D-2-hydroxyglutarate and the mitochondrial electron transport chain.

  DOI：

  10.1016/j.bbapap.2019.07.008
• 作为产物：
  描述：

  葡萄糖 在 potassium dihydrogenphosphate 、 氧气 、 magnesium sulfate 作用下， 以 水 为溶剂， 反应 78.0h， 以77%的产率得到乳酸
  参考文献：
  名称：

  Fermentation process using yeast cells having disrupted pathway from dihydroxyacetone phosphate to glycerol

  摘要：

  公开号：

  EP2586313B1
• 作为试剂：
  描述：

  des-myo-inositol mycothiol 在 乙二胺四乙酸 、 Mycobacterium tuberculosis flavohemoglobin 、 乳酸 作用下， 以 aq. buffer 为溶剂， 反应 0.08h， 生成 myo-inositol mycothiol
  参考文献：
  名称：

  对结核分枝杆菌中黄酮血红蛋白功能的新见解：作为 NADPH 依赖性二硫键还原酶和 D-乳酸依赖性霉菌硫酮还原酶的作用

  摘要：

  结核分枝杆菌(甲基叔丁基醚) 产生一种非常规的黄素血红蛋白 (甲基叔丁基醚FHb) 携带一个类似于 D-乳酸脱氢酶 (D-LDH) 的 FAD 结合位点，并将 D-乳酸氧化成丙酮酸。分子机制甲基叔丁基醚FHb 功能在甲基叔丁基醚仍然未知。我们发现 D-LDH 型 FAD 结合位点在甲基叔丁基醚FHb 与另一个类似于硫氧还蛋白还原酶的 FAD 结合基序重叠，并在存在类似于 trxB 的 NADPH 的情况下减少 DTNB甲基叔丁基醚. 这些结果表明甲基叔丁基醚FHb 起二硫化物氧化还原酶的作用。有趣的是，D-乳酸在甲基叔丁基醚FHb 并减弱其氧化 NADPH 的能力。质谱分析表明甲基叔丁基醚FHb 降低了DES-肌-与 NADPH 不同，D-乳酸存在下的肌醇分枝杆菌硫醇，表明 D-乳酸改变了甲基叔丁基醚FHb 从二硫醇到二硫醇。什么时候耻垢分枝杆菌携带删除fhbII基因（编码同源物甲基叔丁基

  DOI：

  10.3389/fcimb.2021.796727

文献信息

• Asymmetric transfer hydrogenation by synthetic catalysts in cancer cells
  作者：James P. C. Coverdale、Isolda Romero-Canelón、Carlos Sanchez-Cano、Guy J. Clarkson、Abraha Habtemariam、Martin Wills、Peter J. Sadler

  DOI：10.1038/nchem.2918

  日期：2018.3.1

  cells. The formate precursor N-formylmethionine was explored as an alternative to formate in PC3 prostate cancer cells, which are known to overexpress a deformylase enzyme. Transfer-hydrogenation catalysts that generate reductive stress in cancer cells offer a new approach to cancer therapy.

  低剂量活性的催化抗癌金属药物可以最大限度地减少副作用，引入对抗耐药性的新作用机制并扩大抗癌药物活性的范围。在这里，我们使用高度稳定的手性半夹心有机金属 Os( II ) 芳烃磺酰二胺配合物，[Os(arene)(TsDPEN)] (TsDPEN, N -( p-甲苯磺酰基）-1,2-二苯基乙二胺），以实现丙酮酸的高度对映选择性还原，丙酮酸是代谢途径中的关键中间体。在水性模型系统和人类癌细胞中都显示出还原，其中无毒浓度的甲酸钠用作氢化物源。催化机制产生对卵巢癌细胞与非癌性成纤维细胞（卵巢和肺）的选择性，后者通常用作健康增殖细胞的模型。甲酸前体N-甲酰甲硫氨酸被探索为 PC3 前列腺癌细胞中甲酸的替代物，已知其过表达去甲酰基酶。在癌细胞中产生还原性应力的转移氢化催化剂为癌症治疗提供了一种新方法。
• A chiral spirobifluorene-based bis(salen) zinc(<scp>ii</scp>) receptor towards highly enantioselective binding of chiral carboxylates
  作者：Sk Asif Ikbal、Yoko Sakata、Shigehisa Akine

  DOI：10.1039/d1dt00218j

  日期：——

  We have designed a new chiral receptor based on two salen zinc(II) complex units connected with a spirobifluorene framework. The chiral receptor is proven to enantioselectively bind chiral carboxylate guests and the differences between the binding constants of enantiomeric guests were up to more than one order of magnitude.

  我们设计了一种新的手性受体，它基于两个与螺二芴骨架相连的Salen锌（II）复杂单元。已证明手性受体能对映选择性地结合手性羧酸盐客体，并且对映体客体的结合常数之间的差异高达一个以上的数量级。
• The Crystal Structure of a Homodimeric<i>Pseudomonas</i>Glyoxalase I Enzyme Reveals Asymmetric Metallation Commensurate with Half-of-Sites Activity
  作者：Rohan Bythell-Douglas、Uthaiwan Suttisansanee、Gavin R. Flematti、Michael Challenor、Mihwa Lee、Santosh Panjikar、John F. Honek、Charles S. Bond

  DOI：10.1002/chem.201405402

  日期：2015.1.7

  class of glyoxalase I (Glo1) metalloenzymes are typically homodimeric with two metal‐dependent active sites. While the two active sites share identical amino acid composition, this class of enzyme is optimally active with only one metal per homodimer. We have determined the X‐ray crystal structure of GloA2, a Zn inactive Glo1 enzyme from Pseudomonas aeruginosa. The presented structures exhibit an unprecedented

  乙二醛酶I（Glo1）金属酶的Zn失活类型通常是同二聚体，具有两个金属依赖性的活性位点。尽管两个活性位点共享相同的氨基酸组成，但这类酶在每个同型二聚体中仅含一种金属时具有最佳活性。我们已经确定了GloA2的X射线晶体结构，这是一种来自铜绿假单胞菌的Zn失活的Glo1酶。所呈现的结构展现出前所未有的金属结合排列，与位点一半的活性一致：一个活性位点包含一个激活的Ni 2+离子，而另一个活性位点包含两个失活的Zn 2+离子。双核Zn 2+促进的酶学实验该位点鉴定出GloA2的新的催化性质。除了其先前确定的乙二醛酶I活性外，该酶还可以作为依赖Zn 2+ / Co 2+的水解酶起作用。提出的发现表明，GloA2可以同时容纳两种不同的金属结合结构，每种催化不同的反应。
• Substrate and reaction intermediate mimics as inhibitors of 3-deoxy-d-arabino-heptulosonate 7-phosphate synthase
  作者：Scott R. Walker、Hemi Cumming、Emily J. Parker

  DOI：10.1039/b909241b

  日期：——

  3-Deoxy-D-arabino-heptulosonate 7-phosphate (DAH7P) synthase catalyses the aldol-like addition of phosphoenolpyruvate (PEP) to D-erythrose 4-phosphate in the first step of the shikimate pathway to aromatic amino acids. A series of compounds, designed to mimic intermediates in the enzyme-catalysed reaction, have been synthesised and tested as inhibitors for the DAH7P synthase from Escherichia coli. The most potent inhibitor was the vinyl phosphonate, (E)-2-methyl-3-phosphonoacrylic acid, with a Ki of 4.7 µM.

  3-Deoxy-D-arabino-heptulosonate 7-phosphate (DAH7P) synthase 催化磷酸烯醇丙酮酸 (PEP) 与 D-erythrose 4-phosphate 的醛醇类加成反应，是莽草酸通向芳香族氨基酸的第一步。我们合成并测试了一系列模拟酶催化反应中间产物的化合物，作为大肠杆菌 DAH7P 合成酶的抑制剂。最有效的抑制剂是乙烯基膦酸，(E)-2-甲基-3-膦酰丙烯酸，Ki 为 4.7 µM。
• Preorganized Homochiral Pyrrole‐Based Receptors that Display Enantioselective Anion Binding
  作者：Johannes Karges、Seth M. Cohen

  DOI：10.1002/ejoc.202101346

  日期：2022.4.27

  Herein, a series of tris(pyrrolamide) receptors for anion recognition is presented. The receptors were able to bind to a variety of anions with good affinity, and homochiral receptors produced a 1.6-fold greater affinity for (S)-(+)-mandelate over (R)-(−)-mandelate, demonstrating the ability to differentiate between these enantiomeric anions.

  在此，提出了一系列用于阴离子识别的三(吡咯酰胺)受体。这些受体能够以良好的亲和力与多种阴离子结合，并且纯手性受体对 ( S )-(+)-扁桃酸的亲和力是 ( R )-(−)-扁桃酸的 1.6 倍，这表明其能够区分这些对映体阴离子。