(S)-3,5-二羟基苯基甘氨酸 | 162870-29-3

• 物质功能分类: 生物化工 - 抑制剂
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: (S)-3,5-二羟基苯基甘氨酸
• 英文名称: (S)-3,5-dihydroxyphenylglycine
• 英文别名: DHPG；L-3,5-dihydroxyphenylglycine；3,5-dihydroxyphenylglycine；3,5-DHPG；(S)-3,5-DHPG；(2S)-azaniumyl(3,5-dihydroxyphenyl)acetate；(2S)-2-azaniumyl-2-(3,5-dihydroxyphenyl)acetate
• CAS: 162870-29-3
• 化学式: C₈H₉NO₄
• 分子量: 183.164
• InChiKey: HOOWCUZPEFNHDT-ZETCQYMHSA-N

物化性质

• 熔点：
  >207°C (dec.)
• 沸点：
  448.8±33.0 °C(Predicted)
• 密度：
  1.550±0.06 g/cm3(Predicted)
• 溶解度：
  水基（微溶，超声处理）、甲醇（微量溶解）、水（微溶，加热）

计算性质

• 辛醇/水分配系数(LogP)：
  -2.4
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  104
• 氢给体数：
  4
• 氢受体数：
  5

安全信息

• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• 海关编码：
  2922509090
• 安全说明：
  S26

制备方法与用途

生物活性(S)-3,5-DHPG 是一种效力不高但具有选择性的 I 组代谢型谷氨酸受体 (mGluRs) 激动剂，对 mGluR1a 和 mGluR5a 的 Ki 值分别为 0.9 µM 和 3.9 µM。在缺氧大鼠中，(S)-3,5-DHPG 表现出抗焦虑活性。

靶点

• mGluR1a：0.9 μM (Ki)
• mGluR5a：3.9 μM (Ki)

体外研究

(S)-3,5-DHPG 特异性地结合到高亲和力喹尼酸位点，即假设为 I 组 mGlu 结合位点。

体内研究

在 160-180 g 体重的雄性 Wistar 大鼠中，通过脑室内注射 (S)-3,5-DHPG (0.01, 0.1 和 1.0 nmol/5 μL)，其能剂量依赖地改善记忆巩固和检索，并表现出抗焦虑活性。

反应信息

• 作为反应物：
  描述：

  (S)-3,5-二羟基苯基甘氨酸 在 p-hydroxyphenylglycine transaminase 磷酸吡哆醛 、 2-氧代-戊二酸离子(2-) 、 三羟甲基氨基甲烷盐酸盐 作用下， 反应 1.0h， 生成 Di-meta-hydroxyphenylglyoxylic acid
  参考文献：
  名称：

  Biosynthesis of the di-meta-hydroxyphenylglycine constituent of the vancomycin-group antibiotic chloroeremomycin

  摘要：

  The biosynthetic pathway to the L-di-meta-hydroxyphenylglycine (DHPG) constituent of chloroeremomycin (A82846B), has been investigated by a combination of feeding experiments with 13C-labelled substrates, and expression and assay of HpgT from the chloroeremomycin biosynthetic cluster.

  DOI：

  10.1039/b103668h
• 作为产物：
  描述：

  2-amino-2-(3,5-dihydroxyphenyl)acetonitrile 在 α-aminonitrilase NIT191 from Burkholderia xenovorans 作用下， 以 aq. phosphate buffer 为溶剂， 以99%的产率得到
  参考文献：
  名称：

  Large α-aminonitrilase activity screening of nitrilase superfamily members: Access to conversion and enantiospecificity by LC–MS

  摘要：

  DOI：

  10.1016/j.molcatb.2014.05.019

文献信息

• A Facile Fmoc Solid Phase Synthesis Strategy To Access Epimerization-Prone Biosynthetic Intermediates of Glycopeptide Antibiotics
  作者：Clara Brieke、Max J. Cryle

  DOI：10.1021/ol500840f

  日期：2014.5.2

  Fmoc-chemistry for the solid phase peptide synthesis of vancomycin- and teicoplanin-type peptides is described. Epimerization of highly racemization-prone arlyglycine derivatives is suppressed through optimized Fmoc-deprotection and coupling conditions. Starting from easily accessible Fmoc-protected amino acids, this strategy enables the enantioselective synthesis of peptides corresponding to intermediates

  描述了一种基于Fmoc化学的快速方案，用于万古霉素和替考拉宁型肽的固相肽合成。通过优化的Fmoc脱保护和偶联条件，可抑制高度消旋化的芳基甘氨酸衍生物的差向异构化。从容易获得的受Fmoc保护的氨基酸开始，这种策略使肽的对映选择性合成与万古霉素和替考拉宁生物合成中发现的中间体相对应，具有优异的纯度和高收率（38％–71％）。
• [EN] BIOLOGICAL FERMENTATION USING DIHYDROXYACETONE AS A SOURCE OF CARBON<br/>[FR] FERMENTATION BIOLOGIQUE UTILISANT DE LA DIHYDROXYACÉTONE COMME SOURCE DE CARBONE
  申请人：KEMBIOTIX LLC

  公开号：WO2017139420A1

  公开（公告）日：2017-08-17

  The present invention relates to the use of hydrocarbons derived from natural gas in the fermentative production of biochemicals including biofuels. More specifically, the present invention provides the method for manufacturing dihydroxyacetone ("DHA") from natural gas, biogas, biomass and CO2 released from industrial plants including electricity-generating plants, steel mills and cement factories and the use of DHA as a source of organic carbon in the fermentative production of biochemicals including biofuels. The present invention comprises three stages. In the first stage of the present invention, syngas and formaldehyde are produced from natural gas, biogas, biomass and CO2 released from industrial plants. In the second stage of the present invention, formaldehyde and syngas are condensed to produce DHA. In the third stage of the present invention, biochemicals including biofuels are produced from DHA using fermentation process involving wild type or genetically modified microbial biocatalysts.

  本发明涉及使用从天然气中提取的碳氢化合物在生物化学品，包括生物燃料的发酵生产中的应用。更具体地说，本发明提供了一种从天然气、沼气、生物质和工业厂房中释放的CO2中制造二羟基丙酮（"DHA"）的方法，以及将DHA作为有机碳源在发酵生产中制造生物化学品，包括生物燃料的应用。本发明包括三个阶段。在本发明的第一阶段中，从天然气、沼气、生物质和工业厂房中释放的 中产生合成气和甲醛。在本发明的第二阶段中，甲醛和合成气被凝结成DHA。在本发明的第三阶段中，使用野生型或基因改造的微生物生物催化剂进行发酵过程，从DHA中生产生物化学品，包括生物燃料。
• Capture compounds, collections thereof and methods for analyzing the proteome and complex compositions
  申请人：Köster Hubert

  公开号：US20110118136A1

  公开（公告）日：2011-05-19

  Capture compounds and collections thereof and methods using the compounds for the analysis of biomolecules are provided. In particular, collections, compounds and methods are provided for analyzing complex protein mixtures, such as the proteome. The compounds are multifunctional reagents that provide for the separation and isolation of complex protein mixtures. Each compound has the formula: wherein: Z is a trityl derivative; X, the reactivity function, covalently binds to amino acid side chains of proteins; Y, the selectivity function, modulates binding of X to the amino acid side chains in proteins such that X binds to fewer proteins when Y is present than in its absence; and Q permits separation or immobilization of the capture compound. Automated systems for performing the methods also are provided.

  本文提供了捕获化合物和化合物集合以及使用这些化合物进行生物分子分析的方法。特别地，提供了用于分析复杂蛋白质混合物（如蛋白质组）的集合、化合物和方法。这些化合物是多功能试剂，可用于分离和分离复杂蛋白质混合物。每个化合物的公式为：其中：Z是三苯甲基衍生物；X是反应性功能，共价结合到蛋白质的氨基酸侧链上；Y是选择性功能，调节X与蛋白质中氨基酸侧链的结合，使得在Y存在时，X与较少的蛋白质结合，而在Y不存在时，X与更多的蛋白质结合；Q允许分离或固定捕获化合物。本文还提供了用于执行这些方法的自动化系统。
• Biosynthesis of L-p-hydroxyphenylglycine, a non-proteinogenic amino acid constituent of peptide antibiotics**Supported in part by NIH grant GM 49338.
  作者：Brian K Hubbard、Michael G Thomas、Christopher T Walsh

  DOI：10.1016/s1074-5521(00)00043-0

  日期：2000.12

  Background: The non-proteinogenic amino acid phydroxyphenylglycine is a crucial component of certain peptidic natural products synthesized by a nonribosomal peptide synthetase mechanism. In particular, for the vancomycin group of antibiotics phydroxyphenylglycine plays a structural role in formation of the rigid conformation of the central heptapeptide aglycone in addition to being the site of glycosylation, Initial labeling studies suggested tyrosine was a precursor of phydroxyphenylglycine but the specific steps in p-hydroxyphenylglycine biosynthesis remained unknown. Recently, the sequencing of the chloroeremomycin gene cluster from Amycolatopsis orientalis gave new insights into the biosynthetic pathway and allowed for the prediction of a four enzyme pathway leading to L-p-hydroxyphenylglycine from the common metabolite prephenate.Results: We have characterized three of the four proposed enzymes of the L-p-hydroxyphenylglycine biosynthetic pathway. The three enzymes are encoded by open reading frames (ORFs) 21, 22 and 17 (ORF21: [PCZA361,1, 052791, CAA1 1761]; ORF22: [PCZA361.2, O52792, CAA11762]; ORF17, [PCZA361.25, O52815, CAA11790]), of the chloroeremomycin biosynthetic gene cluster and we show they have p-hydroxymandelate synthase, p-hydroxymandelate oxidase and L-p-hydroxyphenylglycine transaminase activities, respectively.Conclusions: The L-p-hydroxyphenylglycine biosynthetic pathway shown here is proposed to be the paradigm for how this non-proteinogenic amino acid is synthesized by microorganisms incorporating it into peptidic natural products. This conclusion is supported by the finding of homologs for the four L-p-hydroxyphenylpyruvate biosynthetic enzymes in four organisms known to synthesize peptidic natural products that contain p-hydroxyphenylglycine. Three of the enzymes are proposed to function in a cyclic manner in vivo with L-tyrosine being both the amino donor for L-p-hydroxyphenylglycine and a source of p-hydroxyphenylpyruvate, an intermediate in the biosynthetic pathway.
• NOVEL USES FOR DRUGS TARGETING GLUTAMINE SYNTHETASE
  申请人：Roegel Jean-Christophe

  公开号：US20090209474A1

  公开（公告）日：2009-08-20

  The present invention relates to novel therapeutic uses of tianeptine, salts, isomers, pro-drugs, metabolites and structural analogs thereof. Furthermore, the present invention relates to the use of tianeptine, salts, isomers, pro-drugs, metabolites and structural analogs thereof, in obtaining methods of screening and of developing drugs. Finally, the present invention relates to the novel therapeutic use of other glutamine synthetase (GS) ligands and to the use of these ligands in obtaining methods for screening and developing drugs.