4-Hydroxyphenylacetate

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-Hydroxyphenylacetate
• 英文别名: 2-(4-hydroxyphenyl)acetate
• 化学式: C8H7O3-
• 分子量: 151.14
• InChiKey: XQXPVVBIMDBYFF-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  4-Hydroxyphenylacetate 、 2-溴-5-醛基吡啶 、 potassium carbonate 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以afforded [4-(5-formyl-pyridin-2-yloxy)-phenyl]-acetic acid methyl ester (814 mg)的产率得到[4-(5-Formyl-pyridin-2-yloxy)-phenyl]-acetic acid methyl ester
  参考文献：
  名称：

  Chemokine receptor binding compounds

  摘要：

  本发明涉及化学因子受体结合化合物、药物组合物及其使用。更具体地，本发明涉及化学因子受体活性调节剂，优选地为CCR4或CCR5的调节剂。在一个方面，这些化合物表现出对人类免疫缺陷病毒（HIV）感染靶细胞的保护效应。

  公开号：

  US20070066624A1
• 作为产物：
  描述：

  4-hydroxyphenylpyruvate 、 氧气 生成 4-Hydroxyphenylacetate 、 二氧化碳
  参考文献：
  名称：

  The catabolism of L-tyrosine by an Arthrobacter sp.

  摘要：

  一株Arthrobacter sp.通过涉及3,4-二羟基苯乙酸作为关键中间体的途径代谢L-酪氨酸。通过一种特异性需要α-酮戊二酸活性的氨基转移酶，从酪氨酸形成对羟基苯丙酮，然后通过氧化脱羧反应转化为对羟基苯乙酸。对羟基苯乙醛不是对羟基苯乙酸形成的中间体。该细菌的提取物将3,4-二羟基苯乙酸氧化为δ-羧甲基-α-羟基樟酸，当加入2摩尔的二磷酸脉冲核苷酸时，会产生等量的琥珀酸和丙酮酸。

  DOI：

  10.1139/m77-169

文献信息

• Gas Barrier Laminated Film and Process for Producing the Same
  申请人：Fujii Hitoshi

  公开号：US20070269664A1

  公开（公告）日：2007-11-22

  There are provided a gas barrier laminated film, which is transparent while possessing excellent gas barrier properties and, at the same time, has excellent impact resistance, and a process for producing the same. The gas barrier laminated film comprises a base material, a vapor deposited film of an inorganic oxide provided on the base material, and a gas barrier coating film provided on the vapor deposited film. The gas barrier laminated film is characterized in that the base material on its side where the vapor deposited film is provided, has been subjected to pretreatment or primer coating treatment, and the gas barrier coating film has been formed by coating a gas barrier coating liquid onto the inorganic oxide film and then heating the coating.

  提供了一种气体阻隔层压膜，它在具有优异气体阻隔性能的同时，具有优异的抗冲击性，且透明。同时提供了制备该压膜的方法。该气体阻隔层压膜包括基材、沉积在基材上的无机氧化物蒸发膜和涂覆在蒸发膜上的气体阻隔涂层膜。该气体阻隔层压膜的特点在于，在蒸发膜所在的基材侧经过预处理或底漆涂层处理，并且气体阻隔涂层膜是通过将气体阻隔涂层液体涂覆在无机氧化物膜上并加热涂覆形成的。
• Metabolic function and properties of 4-hydroxyphenylacetic acid 1-hydroxylase from Pseudomonas acidovorans
  作者：W A Hareland、R L Crawford、P J Chapman、S Dagley

  DOI：10.1128/jb.121.1.272-285.1975

  日期：1975.1

  also for the observation that when 4-hydroxyphenoxyacetic acid was attacked by the enzyme, hydroquinone was formed by release of the side chain, probably as glycolic acid. Only one enantiometer of racemic 4-hydroxyhydratropic acid was attacked by 4-HPA 1-hydroxylase; the product, alpha-methylhomogentisic acid (2-(2,5-dihydroxyphenyl)-propionic acid), exhibited optical activity. This observation suggests

  在假单胞菌中诱导了4-羟基苯乙酸酶NAD（P）H：氧氧化还原酶（1-羟基化）（EC 1.14.13 ...； 4-羟基苯乙酸1-单加氧酶；在此称为4-HPA 1-羟基酶）。当使用4-羟基苯乙酸盐（4-PHA）作为生长的碳源时为酸性卵。尿精和马来酰乙酰乙酸酯是4-HPA降解的中间体。通过超速离心细胞提取物获得了一种不含羟尿酸双加氧酶的羟化酶制剂，该制剂可在二硫赤藓糖醇存在下于4℃保存，活性几乎没有损失。但是当通过亲和色谱法纯化18倍时，酶变得不稳定。充分活性需要黄素腺嘌呤二核苷酸和Mg2 +离子。4-HPA 1-羟化酶被KCl抑制，这与4-HPA竞争。确定的与4-HPA竞争的抑制剂的Ki值为17μMdl-4-羟基扁桃酸，43μM3,4-二羟基苯基乙酸，87μM4-羟基-3-甲基苯基乙酸和440μM4-羟基苯基丙酸。4-HPA 1-羟化酶底物的表观Km值为31μM4-HPA，67μM氧气，95
• Initial catabolism of aromatic biogenic amines by Pseudomonas aeruginosa PAO: pathway description, mapping of mutations, and cloning of essential genes
  作者：S M Cuskey、V Peccoraro、R H Olsen

  DOI：10.1128/jb.169.6.2398-2404.1987

  日期：1987.6

  Pseudomonas aeruginosa PAO1 was able to utilize several aromatic biogenic amines as sole sources of carbon or nitrogen. These included the phenethylamines tyramine and dopamine and the phenethanolamines octopamine, synephrine, and norepinephrine. Initial catabolism of the phenethylamines was mediated by a membrane-bound tyramine dehydrogenase which produced 4-hydroxyphenylacetaldehyde (4HPAL) with tyramine as the substrate. The enzyme was induced by growth with both classes of amines. Initial catabolism of octopamine (except when present as the sole source of carbon and nitrogen) was mediated by a soluble enzyme with activity against the phenethanolamines but not against tyramine or dopamine. The product of the reaction with octopamine as substrate was also 4HPAL. Addition of NAD to reaction mixtures yielded 4-hydroxyphenylacetic acid and NADH. These activities, octopamine hydrolyase and 4-HPAL dehydrogenase (measured as a combined activity, OCAH-4HPALDH), were only induced by growth with phenethanolamines. However, the combined activities were not observed in extracts from cells grown with octopamine as the sole source of carbon and nitrogen, suggesting that an alternate pathway is used under this growth condition. Two independently isolated mutant strains were unable to utilize tyramine as a sole source of carbon or nitrogen. These mutants were also unable to utilize dopamine but grew at wild-type rates on the phenethanolamines. The mutations were mapped at about 70 min on the PAO1 chromosome with the chromosome-mobilizing plasmid R68.45, and both were linked to the catA1, mtu-9002, tyu-9009, and puuE mutations. DNA complementing both of the mutations was cloned on a single BamHI fragment approximately 13.8 kilobase pairs in length. Analysis of a subcloned fragment showed that the two mutations were in different genes.

  假单胞菌PAO1能够利用多种芳香族生物胺作为唯一的碳源或氮源。其中包括苯乙胺、多巴胺和苯基乙醇胺。苯乙胺的初始降解是通过膜结合的苯乙胺脱氢酶介导的，该酶以苯乙胺为底物产生4-羟基苯乙醛（4HPAL）。该酶在两类胺的生长条件下均被诱导。八胺的初始降解（除非八胺作为唯一的碳源和氮源存在）是通过可溶性酶介导的，该酶对苯基乙醇胺具有活性，但对苯乙胺或多巴胺没有活性。以八胺为底物的反应产物也是4HPAL。在反应混合物中加入NAD可产生4-羟基苯乙酸和NADH。这些活性，八胺水解酶和4-HPAL脱氢酶（作为一个联合活性测量，OCAH-4HPALDH），仅在生长于苯基乙醇胺的条件下被诱导。然而，在以八胺作为唯一的碳源和氮源生长的细胞提取物中未观察到这些联合活性，这表明在这种生长条件下使用了另一种途径。两个独立分离的突变株无法利用苯乙胺作为唯一的碳源或氮源。这些突变株也无法利用多巴胺，但在苯基乙醇胺上以野生型速率生长。这些突变位点位于PAO1染色体上的约70分钟处，与染色体移动质粒R68.45相关联，并且两者与catA1、mtu-9002、tyu-9009和puuE突变相关。克隆了能够补充这两种突变的DNA，其长度约为13.8千碱基对的单个BamHI片段。对亚克隆片段的分析表明这两种突变位于不同的基因中。
• Discovery of enzymes for toluene synthesis from anoxic microbial communities
  作者：Harry R. Beller、Andria V. Rodrigues、Kamrun Zargar、Yu-Wei Wu、Avneesh K. Saini、Renee M. Saville、Jose H. Pereira、Paul D. Adams、Susannah G. Tringe、Christopher J. Petzold、Jay D. Keasling

  DOI：10.1038/s41589-018-0017-4

  日期：2018.5

  lake sediments more than three decades ago, but the enzyme catalyzing this biochemically challenging reaction has never been identified. Here we report the toluene-producing enzyme PhdB, a glycyl radical enzyme of bacterial origin that catalyzes phenylacetate decarboxylation, and its cognate activating enzyme PhdA, a radical S-adenosylmethionine enzyme, discovered in two distinct anoxic microbial communities

  三十多年前在缺氧的湖泊沉积物中报告了微生物甲苯的生物合成，但是催化这种生化挑战性反应的酶从未被发现。在这里，我们报告产生甲苯的酶PhdB（一种细菌来源的糖基自由基酶，催化苯乙酸酯的脱羧反应）及其同源活化酶PhdA（一种自由基S）-腺苷甲硫氨酸酶，在两个不同的产生甲苯的缺氧微生物群落中发现。从复杂的微生物群落（> 300,000个基因）而不是从微生物分离物中发现酶的非常规过程涉及宏基因组学和元蛋白质组学支持的生物化学，以及体外重组酶活性的确认。这项工作扩大了已知的糖基自由基酶（以前仅表征了7种反应类型）和产生芳烃的酶的催化范围，并将使首次利用可再生资源（例如木质纤维素生物质）生化合成芳族燃料碳氢化合物成为可能。 ，而不是石油。
• Characterization of the anthranilate degradation pathway in Geobacillus thermodenitrificans NG80-2
  作者：Xueqian Liu、Yangpeng Dong、Xiaomin Li、Yi Ren、Yanxia Li、Wei Wang、Lei Wang、Lu Feng

  DOI：10.1099/mic.0.031880-0

  日期：2010.2.1

  Anthranilate is an important intermediate of tryptophan metabolism. In this study, a hydroxylase system consisting of an FADH₂-utilizing monooxygenase (GTNG_3160) and an FAD reductase (GTNG_3158), as well as a bifunctional riboflavin kinase/FMN adenylyltransferase (GTNG_3159), encoded in the anthranilate degradation gene cluster inGeobacillus thermodenitrificansNG80-2 were functionally characterizedin vitro. GTNG_3159 produces FAD to be reduced by GTNG_3158 and the reduced FAD (FADH₂) is utilized by GTNG_3160 to convert anthranilate to 3-hydroxyanthranilate (3-HAA), which is further degraded to acetyl-CoA through ameta-cleavage pathway also encoded in the gene cluster. Utilization of this pathway for the degradation of anthranilate and tryptophan by NG80-2 under physiological conditions was confirmed by real-time RT-PCR analysis of representative genes. This is believed to be the first time that the degradation pathway of anthranilate via 3-HAA has been characterized in a bacterium. This pathway is likely to play an important role in the survival ofG. thermodenitrificansin the oil reservoir conditions from which strain NG80-2 was isolated.

  Anthranilate是色氨酸代谢的重要中间体。在这项研究中，位于Geobacillus thermodenitrificans NG80-2的anthranilate降解基因簇中编码的一个由FAD还原酶（GTNG_3158）和一个FADH2利用单加氧酶（GTNG_3160）组成的羟化酶系统，以及一个双功能核黄素激酶/FMN腺苷酰转移酶（GTNG_3159）在体外进行了功能特性描述。GTNG_3159产生FAD，被GTNG_3158还原，而还原的FAD（FADH2）被GTNG_3160利用，将anthranilate转化为3-羟基anthranilate（3-HAA），后者通过基因簇中编码的meta-断裂途径进一步降解为乙酰辅酶A。通过代表性基因的实时RT-PCR分析，证实了NG80-2在生理条件下利用此途径降解anthranilate和色氨酸。这被认为是第一次在细菌中表征了通过3-HAA的anthranilate降解途径。这条途径很可能在NG80-2分离的油藏条件下发挥重要作用，有助于其生存。