3-(Indol-3-yl)lactate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3-(Indol-3-yl)lactate
• 英文别名: 2-hydroxy-3-(1H-indol-3-yl)propanoate
• 化学式: C11H10NO3-
• 分子量: 204.2
• InChiKey: XGILAAMKEQUXLS-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  76.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(Indol-3-yl)lactate 、 nicotinamide adenine dinucleotide 生成 氢(+1)阳离子 、 indole-3-pyruvate 、 NADH
  参考文献：
  名称：

  辅酶A酯参与了产气荚膜梭菌（R.-phenyllactate）脱水生成（E）-肉桂酸酯的过程。

  摘要：

  在L-苯丙氨酸上厌氧生长的产孢梭状芽孢杆菌的苯乳酸脱水酶催化（R）-苯乳酸可逆脱水合成为（E）-肉桂酸酯。纯化产生由FldA（46kDa），F1dB（43kDa）和FldC（40kDa）组成的异三聚酶复合物（130 +/- 15kDa）。通过对Q-琼脂糖进行重层析，可以分离出FldA的大部分，并将其鉴定为对氧不敏感的肉桂酰基-CoA：苯基乳酸CoA-转移酶，而消耗转移酶的三聚体保留了对氧敏感的苯基乳酸脱水酶的活性，并含有约一个[4Fe- 4S]群集。脱水酶活性需要10 microM FAD，0.4 mM ATP，2.5 mM MgCl2、0.1 mM NADH，5 microM肉桂酰-CoA和少量无细胞提取物（每毫升10 microg蛋白）类似于酸发酵球菌中的2-羟基戊二酰-CoA脱水酶。均质的FldA的N-末端（39个氨基酸）与大肠杆菌中的肉碱代谢有关的CaiB的N-末端（39％序列同一

  DOI：

  10.1046/j.1432-1327.2000.01427.x

文献信息

• A gut bacterial pathway metabolizes aromatic amino acids into nine circulating metabolites
  作者：Dylan Dodd、Matthew H. Spitzer、William Van Treuren、Bryan D. Merrill、Andrew J. Hryckowian、Steven K. Higginbottom、Anthony Le、Tina M. Cowan、Garry P. Nolan、Michael A. Fischbach、Justin L. Sonnenburg

  DOI：10.1038/nature24661

  日期：2017.11

  profiling to characterize a pathway from the gut symbiont Clostridium sporogenes that generates aromatic amino acid metabolites. Our results reveal that this pathway produces twelve compounds, nine of which are known to accumulate in host serum. All three aromatic amino acids (tryptophan, phenylalanine and tyrosine) serve as substrates for the pathway, and it involves branching and alternative reductases for

  人类肠道微生物群会产生数十种代谢物，这些代谢物会在血液中积累，从而对宿主产生全身性影响。尽管这些小分子的浓度通常与药剂达到的浓度相似，但对产生它们的微生物代谢途径知之甚少。在这里，我们结合遗传学和代谢分析来表征来自肠道共生体孢子梭菌的产生芳香族氨基酸代谢物的途径。我们的结果表明，该途径产生 12 种化合物，其中 9 种已知会在宿主血清中积累。所有三种芳香族氨基酸（色氨酸、苯丙氨酸和酪氨酸）均作为该途径的底物，它涉及特定中间体的分支和替代还原酶。通过基因操纵 C. sporogenes，我们调节无菌小鼠中这些代谢物的血清水平，并表明这反过来影响肠道通透性和全身免疫。这项工作有可能为系统地努力设计肠道细菌群落的分子输出提供基础。
• Indolelactate dehydrogenase from <i>Clostridium sporogenes</i>
  作者：Marcel Jean、R. D. DeMoss

  DOI：10.1139/m68-068

  日期：1968.4.1

  Indolelactate dehydrogenase has been purified 13-fold from cell-free extracts of Clostridium sporogenes. The enzyme is inactive with lactate, but active with indolelactate, phenyllactate, and p-hydroxyphenyllactate, and utilizes nicotinamide adenine dinucleotide (NAD) but not nicotinamide adenine dinucleotide phosphate NADP (1), as coenzyme. The reaction is reversible; the equilibrium constant is 6.3 × 10⁻6 M at pH 7.0, expressed as [indolepyruvate] [NADH] [H⁺]/[indolelactate] [NAD].The enzyme preparation exhibits regular Michaelis–Menten kinetics with respect to indolelactate, NAD, and NADP, but not with respect to indolepyruvate.

  吲哚乳酸脱氢酶已从Clostridium sporogenes的无细胞提取物中纯化13倍。该酶对乳酸不活性，但对吲哚乳酸、苯乳酸和对羟基苯乳酸活性，并且利用尼古丁酰胺腺嘌呤二核苷酸（NAD）而不是尼古丁酰胺腺嘌呤二核苷酸磷酸盐（NADP）作为辅酶（1）。该反应是可逆的，平衡常数在pH 7.0时为6.3×10^-6 M，表示为[吲哚丙酮酸][NADH][H⁺]/[吲哚乳酸][NAD]。该酶制备在吲哚乳酸、NAD和NADP方面显示出常规的米氏动力学，但在吲哚丙酮酸方面不是这样。
• On the occurrence of enoate reductase and 2-oxo-carboxylate reductase in clostridia and some observations on the amino acid fermentation by Peptostreptococcus anaerobius
  作者：Hermine Giesel、Helmut Simon

  DOI：10.1007/bf00419482

  日期：——

  Enoate reductase present in Clostridium kluyveri and Clostridium spec. La 1 could be detected in three strains of C. tyrobutyricum and ten clostridia belonging to the groups of proteolytic and saccharolytic or proteolytic species, respectively. In C. pasteurianum, C. butyricum and C. propionicum enoate reductase could not be found even after growth on (E)-2-butenoate. A 2-oxo-carboxylate reductase was present in rather low activities in the non-proteolytic clostridia which produce enoate reductase. High activities (up to 10 U/mg protein) of 2-oxo-carboxylate reductase were found in six of ten proteolytic clostridia. The substrate specificities of the enoate reductase and the 2-oxo-carboxylate reductases from the proteolytic clostridia were determined with different alpha, beta-unsaturated carboxylates (enoates) and 2-oxo-carboxylates, respectively. Enoates as well as 2-oxo-carboxylates are intermediates of the pathway by which amino acids are degraded. An explanation is offered for the long known but not understood fact that in the Stickland reaction isoleucine always acts as an electron donor and leucine and phenylalanine can be electron acceptors as well as donors. Peptostreptococcus anaerobius converting some amino acids to the same products as C. sporogenes did this also with the intermediates which were found for the reductive deamination of amino acids in C. sporogenes, however, in crude extracts reduction of enoates occurred only in an activated form.