(S)-4-Hydroxymandelate

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (S)-4-Hydroxymandelate
• 英文别名: (2S)-2-hydroxy-2-(4-hydroxyphenyl)acetate
• 化学式: C8H7O4-
• 分子量: 167.14
• InChiKey: YHXHKYRQLYQUIH-ZETCQYMHSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  12
• 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：
  80.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-4-Hydroxymandelate 、 氧气 生成 p-Hydroxybenzoylformate 、 双氧水
  参考文献：
  名称：

  万古霉素类抗生素中两个不寻常氨基酸的生物合成中涉及的羟基扁桃酸酯氧化酶的表征。

  摘要：

  来自氯霉素霉素基因簇的ORF22已经被克隆，表达和表征为羟基扁桃酸酯氧化酶（HmO），其参与（S）-4-羟基苯基甘氨酸和（S）-3,5-二羟基苯基甘氨酸的形成。

  DOI：

  10.1039/b103548g
• 作为产物：
  描述：

  4-hydroxyphenylpyruvate 、 氧气 生成 (S)-4-Hydroxymandelate 、 二氧化碳
  参考文献：
  名称：

  Biosynthesis of L-p-hydroxyphenylglycine, a non-proteinogenic amino acid constituent of peptide antibiotics**Supported in part by NIH grant GM 49338.

  摘要：

  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.

  DOI：

  10.1016/s1074-5521(00)00043-0

文献信息

• Purification and Properties of l-4-Hydroxymandelate Oxidase from Pseudomonas convexa
  作者：Santhoor G. BHAT、Chelakara S. VAIDYANATHAN

  DOI：10.1111/j.1432-1033.1976.tb10818.x

  日期：1976.9

  An inducible membrane-bound L-4-hydroxymandelate oxidase (decarboxylating) from Pseudomonas convexa has been solubilized and partially purified. It catalyzes the conversion of L-4-hydroxymandelic acid to 4-hydroxybenzaldehyde in a single step with the stoichiometric consumption of O2 and liberation of CO2. The enzyme is optimally active at pH 6.6 and at 55 degrees C. It requires FAD and Mn2+ for its

  来自凸假单胞菌的可诱导的膜结合的L-4-羟基扁桃酸酯氧化酶（脱羧）已被溶解并部分纯化。它以化学计量的O2消耗和CO2的释放，一步催化L-4-羟基扁桃酸转化为4-羟基苯甲醛。该酶在pH 6.6和55摄氏度下具有最佳活性。它的活性需要FAD和Mn2 +。膜结合酶比溶解和纯化的酶更稳定。溶解后，保持在5摄氏度时逐渐失去活性，可以通过冷冻和解冻将其完全活化。DL-4-羟基扁桃酸酯和FAD的Km值分别为0.44 mM和0.038 mM。该酶对DL-4-羟基扁桃酸具有高度特异性。DL-3,4-二羟基扁桃酸竞争性抑制酶反应。根据狄克逊图，DL-3,4-二羟基扁桃酸的Ki值为1.8 X 10（-4）M。该酶完全被硫醇化合物灭活，不受硫醇抑制剂的影响。该酶还被变性剂，重金属离子和螯合剂抑制。
• Purification and properties of l-mandelate-4-hydroxylase from Pseudomonas convexa
  作者：S.G. Bhat、C.S. Vaidyanathan

  DOI：10.1016/0003-9861(76)90170-3

  日期：1976.9