2-hydroxy-2,4E-hexadienedioate | 133191-11-4

• 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: 2-hydroxy-2,4E-hexadienedioate
• 英文别名: 2-hydroxymuconate anion；2-Hydroxymuconate；(2Z,4E)-6-hydroxy-2-oxido-6-oxohexa-2,4-dienoate
• CAS: 133191-11-4
• 化学式: C₆H₄O₅
• 分子量: 156.095
• InChiKey: JBEBGTMCZIGUTK-TZFCGSKZSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-hydroxy-2,4E-hexadienedioate 在 disodium hydrogenphosphate 、 sodium dihydrogenphosphate 、 sodium chloride 作用下， 以 甲醇 、 水 为溶剂， 生成 4-Oxalocrotonate
  参考文献：
  名称：

  Whitman, Christian P.; Aird, Bruce A.; Gillespie, William R., Journal of the American Chemical Society, 1991, vol. 113, # 8, p. 3154 - 3162

  摘要：

  DOI：
• 作为产物：
  描述：

  4-Oxalocrotonate 在 disodium hydrogenphosphate 、 sodium dihydrogenphosphate 、 sodium chloride 作用下， 以 甲醇 、 水 为溶剂， 生成 2-hydroxy-2,4E-hexadienedioate
  参考文献：
  名称：

  Whitman, Christian P.; Aird, Bruce A.; Gillespie, William R., Journal of the American Chemical Society, 1991, vol. 113, # 8, p. 3154 - 3162

  摘要：

  DOI：

文献信息

• Metabolism of 4-Amino-3-hydroxybenzoic Acid by<i>Bordetella</i>sp. Strain 10d: A Different Modified<i>Meta</i>-Cleavage Pathway for 2-Aminophenols
  作者：Chika ORII、Shinji TAKENAKA、Shuichiro MURAKAMI、Kenji AOKI

  DOI：10.1271/bbb.60264

  日期：2006.11.23

  Bordetella sp. strain 10d metabolizes 4-amino-3-hydroxybenzoic acid via 2-hydroxymuconic 6-semialdehyde. Cell extracts from 4-amino-3-hydroxybenzoate-grown cells showed high NAD+-dependent 2-hydroxymuconic 6-semialdehyde dehydrogenase, 4-oxalocrotonate tautomerase, 4-oxalocrotonate decarboxylase, and 2-oxopent-4-enoate hydratase activities, but no 2-hydroxymuconic 6-semialdehyde hydrolase activity. These enzymes involved in 4-amino-3-hydroxybenzoate metabolism were purified and characterized. When 2-hydroxymuconic 6-semialdehyde was used as substrate in a reaction mixture containing NAD+ and cell extracts from 4-amino-3-hydroxybenzoate-grown cells, 4-oxalocrotonic acid, 2-oxopent-4-enoic acid, and 4-hydroxy-2-oxovaleric acid were identified as intermediates, and pyruvic acid was identified as the final product. A complete pathway for the metabolism of 4-amino-3-hydroxybenzoic acid in strain 10d is proposed. Strain 10d metabolized 2-hydroxymuconic 6-semialdehyde derived from 4-amino-3-hydroxybenzoic acid via a dehydrogenative route, not via a hydrolytic route. This proposed metabolic pathway differs considerably from the modified meta-cleavage pathway of 2-aminophenol and those previously reported for methyl- and chloro-derivatives.

  Bordetella sp. 10d株通过2-羟基穆康酸6-半醛代谢4-氨基-3-羟基苯甲酸。来自于培养于4-氨基-3-羟基苯甲酸的细胞的细胞提取物显示出高水平的NAD+-依赖性2-羟基穆康酸6-半醛脱氢酶、4-草酰克罗通酸互变异构酶、4-草酰克罗通酸脱羧酶和2-氧戊-4-烯酸水合酶活性，但没有检测到2-羟基穆康酸6-半醛水解酶活性。这些参与4-氨基-3-羟基苯甲酸代谢的酶被纯化并进行了特征分析。当在含有NAD+和来自于4-氨基-3-羟基苯甲酸的细胞提取物的反应混合物中使用2-羟基穆康酸6-半醛作为底物时，4-草酰克罗通酸、2-氧戊-4-烯酸和4-羟基-2-氧戊酸被鉴定为中间产物，而丙酮酸被鉴定为最终产物。提出了10d株对4-氨基-3-羟基苯甲酸的完整代谢途径。10d株通过脱氢途径代谢由4-氨基-3-羟基苯甲酸衍生的2-羟基穆康酸6-半醛，而不是通过水解途径。这种提议的代谢途径与2-氨基酚的改良元断裂途径以及之前报道的甲基和氯衍生物的途径有显著不同。
• Uncovering the Protocatechuate 2,3-Cleavage Pathway Genes
  作者：Daisuke Kasai、Toshihiro Fujinami、Tomokuni Abe、Kohei Mase、Yoshihiro Katayama、Masao Fukuda、Eiji Masai

  DOI：10.1128/jb.00840-09

  日期：2009.11

  Paenibacillus sp. (formerly Bacillus macerans ) strain JJ-1b is able to grow on 4-hydroxybenzoate (4HB) as a sole source of carbon and energy and is known to degrade 4HB via the protocatechuate (PCA) 2,3-cleavage pathway. However, none of the genes involved in this pathway have been identified. In this study, we identified and characterized the JJ-1b genes for the 4HB catabolic pathway via the PCA 2,3-cleavage pathway, which consisted of praR and praABEGFDCHI . Based on the enzyme activities of cell extracts of Escherichia coli carrying praI , praA , praH , praB , praC , and praD , these genes were found to code for 4HB 3-hydroxylase, PCA 2,3-dioxygenase, 5-carboxy-2-hydroxymuconate-6-semialdehyde decarboxylase, 2-hydroxymuconate-6-semialdehyde dehydrogenase, 4-oxalocrotonate (OCA) tautomerase, and OCA decarboxylase, respectively, which are involved in the conversion of 4HB into 2-hydroxypenta-2,4-dienoate (HPD). The praE , praF , and praG gene products exhibited 45 to 61% amino acid sequence identity to the corresponding enzymes responsible for the catabolism of HPD to pyruvate and acetyl coenzyme A. The deduced amino acid sequence of praR showed similarity with those of IclR-type transcriptional regulators. Reverse transcription-PCR analysis revealed that praABEGFDCHI constitute an operon, and these genes were expressed during the growth of JJ-1b on 4HB and PCA. praR-praABEGFDCHI conferred the ability to grow on 4HB to E . coli , suggesting that praEGF were functional for the conversion of HPD to pyruvate and acetyl coenzyme A. A promoter analysis suggested that praR encodes a repressor of the pra operon.

  摘要 Paenibacillus sp. Bacillus macerans ）菌株 JJ-1b 能够以 4-hydroxybenzoate (4HB) 作为唯一的碳和能量来源进行生长，而且已知它能通过原儿茶酸盐 (PCA) 2,3 裂解途径降解 4HB。然而，参与这一途径的基因尚未被确定。在这项研究中，我们鉴定并描述了通过 PCA 2,3 裂解途径分解 4HB 的 JJ-1b 基因，这些基因包括 praR 和 praABEGFDCHI .根据大肠杆菌细胞提取物的酶活性 大肠杆菌 携带 praI , praA , praH , praB , praC 和 praD 发现这些基因编码 4HB 3-羟化酶、PCA 2,3-二氧 化酶、5-羧基-2-羟基琥珀酸-6-半乳糖醛脱羧酶、2-羟基琥珀酸-6-半乳糖醛脱氢酶、4-oxalocrotonate (OCA) tautomerase 和 OCA decarboxylase，它们分别参与将 4HB 转化为 2-hydroxypenta-2,4-dienoate (HPD)。这些 肽 , praF 和 和 基因产物的氨基酸序列与负责将HPD分解为丙酮酸和乙酰辅酶A的相应酶具有45%至61%的相同性。 praR 的氨基酸序列与 IclR 型转录调节因子的氨基酸序列相似。反转录-PCR分析表明 praABEGFDCHI 构成一个操作子，这些基因在 JJ-1b 在 4HB 和 PCA 上的生长过程中表达。 praR-praABEGFDCHI 将在 4HB 上生长的能力赋予了 E . 大肠杆菌 表明 启动子分析表明 启动子分析表明，praEGF praR 的抑制因子。 启动子 操作子的抑制因子。
• Metabolism of resorcinylic compounds by bacteria: new pathway for resorcinol catabolism in Azotobacter vinelandii
  作者：E E Groseclose、D W Ribbons

  DOI：10.1128/jb.146.2.460-466.1981

  日期：1981.5

  We present evidence to document a third pathway for the microbial catabolism of resorcinol. Resorcinol is converted to pyrogallol by resorcinol-grown cells of Azotobacter vinelandii. Pyrogallol is the substrate for one of two ring cleavage enzymes induced by growth with resorcinol. Oxalocrotonate, CO2, pyruvate, and acetaldehyde have been identified as products of pyrogallol oxidation catalyzed by extracts of resorcinol-grown cells. The enzymes pyrogallol 1,2-dioxygenase, oxalocrotonate tautomerase (isomerase), oxalocrotonate decarboxylase, and vinylpyruvate hydratase are present in extracts from resorcinol-grown cells but not in succinate-grown cells.

  我们提供证据，以证明微生物降解间苯二酚的第三种途径。间苯二酚被Azotobacter vinelandii的间苯二酚生长细胞转化为焦高酚。焦高酚是通过与间苯二酚一起生长诱导的两种环裂解酶之一的底物。已经确定焦高酚氧化催化的产物包括草酰丙酸酯、CO2、丙酮酸和乙醛。焦高酚1,2-双加氧酶、草酰丙酸酯互变异构酶、草酰丙酸酯脱羧酶和乙烯丙酮水合酶等酶存在于间苯二酚生长细胞的提取物中，但不存在于琥珀酸生长的细胞中。
• Kinetic and Stereochemical Analysis of YwhB, a 4-Oxalocrotonate Tautomerase Homologue in <i>Bacillus subtilis</i>:  Mechanistic Implications for the YwhB- and 4-Oxalocrotonate Tautomerase-Catalyzed Reactions
  作者：Susan C. Wang、William H. Johnson,、Robert M. Czerwinski、Stacy L. Stamps、Christian P. Whitman

  DOI：10.1021/bi701231a

  日期：2007.10.1

  4-oxalocrotonate tautomerase (4-OT) homologue in Bacillus subtilis, has no known biological role, and the gene has no apparent genomic context. The kinetic and stereochemical properties of YwhB have been examined using available enol and dienol compounds. The kinetic analysis shows that YwhB has a relatively nonspecific 1,3- and 1,5-keto-enol tautomerase activity, with the former activity prevailing. Replacement

  YwhB 是枯草芽孢杆菌中的 4-草酰巴豆酸互变异构酶 (4-OT) 同系物，没有已知的生物学作用，并且该基因没有明显的基因组背景。已经使用可用的烯醇和二烯醇化合物检查了 YwhB 的动力学和立体化学性质。动力学分析表明，YwhB 具有相对非特异性的 1,3-和 1,5-酮-烯醇互变异构酶活性，前者的活性占优势。用丙氨酸替代 Pro-1 或 Arg-11 可显着降低或消除这些活性，表明这两种残基都是这些活性的关键残基。在 D2O 中，两种单酸底物（2-羟基-2,4-戊二烯酸和苯酚丙酮酸）的酮化产生立体异构体 2-keto-3-[2H]-4-戊烯酸和 3-[2H]-苯丙酮酸}的混合物，其中 (3R)-异构体占主导地位。2-羟基-2,4-己二烯二酸酯的酮化，一种二酸，在 D2O 中主要提供相反的对映异构体，(3S)-2-氧代-[3-2H]-4-己烯二酸酯。单酸和二酸显然在 YwhB 的活性位点以不同的方向结合，但使用二酸的
• Overlapping substrate specificities of benzaldehyde dehydrogenase (the xylC gene product) and 2-hydroxymuconic semialdehyde dehydrogenase (the xylG gene product) encoded by TOL plasmid pWW0 of Pseudomonas putida
  作者：J Inoue、J P Shaw、M Rekik、S Harayama

  DOI：10.1128/jb.177.5.1196-1201.1995

  日期：1995.3

  Two aldehyde dehydrogenases involved in the degradation of toluene and xylenes, namely, benzaldehyde dehydrogenase and 2-hydroxymuconic semialdehyde dehydrogenase, are encoded by the xylC and xylG genes, respectively, on TOL plasmid pWW0 of Pseudomonas putida. The nucleotide sequence of xylC was determined in this study. A protein exhibiting benzaldehyde dehydrogenase activity had been purified from

  恶臭假单胞菌TOL质粒pWW0上的xylC和xylG基因分别编码了涉及甲苯和二甲苯降解的两种醛脱氢酶，即苯甲醛脱氢酶和2-羟基粘康半醛脱氢酶。在该研究中确定了xylC的核苷酸序列。已经从恶臭假单胞菌（pWW0）的细胞中纯化了具有苯甲醛脱氢酶活性的蛋白质（JP Shaw和S.Harayama，Eur.J.Biochem.191：705-714，1990）；并且已经从P.Puida的细胞中纯化了蛋白。但是，该蛋白质的氨基末端序列与xylC序列预测的序列不符，但与xylG序列预测的序列一致。因此，在较早的工作中纯化的蛋白质是2-羟基粘康半醛脱氢酶（xylG基因产物）。该蛋白质比苯甲醛（kcat / Km = 3.2 x 10（4）s-更有效地氧化2-羟基粘康半醛（kcat / Km = 1.6 x 10（6）s-1 M-1）证实了这一结论。 1 M-1）。从不合成2-羟基粘康糖醛半醛脱氢酶的恶臭