2,4-Dihydroxy-6-methylbenzoate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,4-Dihydroxy-6-methylbenzoate
• 英文别名: 2-carboxy-5-hydroxy-3-methylphenolate
• 化学式: C8H7O4-
• 分子量: 167.14
• InChiKey: AMKYESDOVDKZKV-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  0
• 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：

  氢(+1)阳离子 、 2,4-Dihydroxy-6-methylbenzoate 生成 二氧化碳 、 3,5-二羟基甲苯
  参考文献：
  名称：

  Studies on Lichen Enzymes. Purification and Properties of Orsellinate Decarboxylase Obtained from Lasallia pustulata

  摘要：

  Orsellinate decarboxylase, catalyzing the decarboxylation of orsellinic acid (2,4‐dihydroxy‐6‐methyl benzoic acid) to orcinol has been isolated from the lichen Lasallia ptulata.The substrate specificity of the enzyme has been tested: only orsellinic acid, 3‐chloro‐, 5‐chloro‐orsellinic acids, homo‐orsellinic acid (2,4‐dihydroxy‐6‐ethyl benzoic acid) and everninic acid (4‐methoxy‐2‐hydroxy‐6‐methyl benzoic acid) were decarboxylated.The obtained degree of purification was 400‐fold with a hal specific activity of 14.1 units/mg of protein. The purified enzyme has a molecular weight of about 72000 (±10%) as determined by dodecyl sulphate‐polyacrylamide gel electrophoresis. The Kmfor orsellinic acid has been determined as 211 μM, the Ki of the inhibitor β‐resorcylic acid (2,4‐dihydroxy benzoic acid) as 800 μM. A spectrophotometric method suitable for the assay of orsellinate decarboxylase is described.

  DOI：

  10.1111/j.1432-1033.1971.tb01567.x
• 作为产物：
  描述：

  水 、 o-Orsellinate depsidate(1-) 生成 氢(+1)阳离子 、 2,4-Dihydroxy-6-methylbenzoate
  参考文献：
  名称：

  Studies on Lichen Enzymes. Purification and Properties of an Orsellinate Depside Hydrolase Obtained from Lasallia pustlata

  摘要：

  From the lichen Lasallia pustulata a new enzyme, “orsellinate depside hydrolase”, capable of catalyzing the hydrolysis of certain depsides to corresponding resorcylic acid monomers, has been isolated.The enzyme is extremely substrate‐specific; only depsides based on orsellinic acid (2,4‐di‐hydroxy‐6‐methyl‐benzoic acid) alone are acceptable. Phenyl benzoate and m‐digallic acid are not hydrolysed. Purification of the enzyme 135‐fold has been achieved with a final specific activity of 1300 U/mg of protein. The enzyme has a molecular weight of 42000 as determined by dodecylsulphate‐polyacrylamide gel electrophoresis. Only a single sharp peak was obtained by analytical ultracentrifugation. Electrofocussing of the hydrolase in polyacrylamide gel resolved the protein into four distinct enzymatically‐active bands. A Km of 56 μM has been determined using the depside lecanoric acid as substrate. The enzyme has been shown to be unusually stable to heat. On treatment of the enzyme for 22 h with 5 mM diisopropylfluorophosphate 75% of the activity was lost, typical of a serine esterase.A spectrophotometric method suitable for the assay of orsellinate depside hydrolase is described.

  DOI：

  10.1111/j.1432-1033.1971.tb01526.x

文献信息

• A Novel Class of Plant Type III Polyketide Synthase Involved in Orsellinic Acid Biosynthesis from Rhododendron dauricum
  作者：Futoshi Taura、Miu Iijima、Eriko Yamanaka、Hironobu Takahashi、Hiromichi Kenmoku、Haruna Saeki、Satoshi Morimoto、Yoshinori Asakawa、Fumiya Kurosaki、Hiroyuki Morita

  DOI：10.3389/fpls.2016.01452

  日期：——

  produces daurichromenic acid, the anti-HIV meroterpenoid consisting of sesquiterpene and orsellinic acid (OSA) moieties. To characterize the enzyme responsible for OSA biosynthesis, a cDNA encoding a novel polyketide synthase (PKS), orcinol synthase (ORS), was cloned from young leaves of R. dauricum. The primary structure of ORS shared relatively low identities to those of PKSs from other plants, and the active

  杜鹃花杜鹃花产生杜里铬酸，一种抗艾滋病毒的类萜，由倍半萜和奥数酸（OSA）部分组成。为了表征负责OSA生物合成的酶，从道夫幼叶中克隆了编码新型聚酮合酶（PKS），蓖麻酚合酶（ORS）的cDNA。ORS的一级结构与其他植物的PKS具有较低的同一性，并且ORS的活性位点具有独特的氨基酸组成。细菌表达的重组ORS接受了乙酰辅酶A作为优选的起始底物，并生产了鸟脚酚作为主要反应产物，以及包括OSA在内的四种次要产物。在这项研究中鉴定出的ORS是第一个生成PKS的植物PKS，该PKS产生乙酸盐衍生的芳族四酮类化合物，例如牛油酚和OSA。有趣的是，
• Complete biosynthetic pathways of ascofuranone and ascochlorin in <i>Acremonium egyptiacum</i>
  作者：Yasuko Araki、Takayoshi Awakawa、Motomichi Matsuzaki、Rihe Cho、Yudai Matsuda、Shotaro Hoshino、Yasutomo Shinohara、Masaichi Yamamoto、Yasutoshi Kido、Daniel Ken Inaoka、Kisaburo Nagamune、Kotaro Ito、Ikuro Abe、Kiyoshi Kita

  DOI：10.1073/pnas.1819254116

  日期：2019.4.23

  expression analysis. Both pathways share the common precursor, ilicicolin A epoxide, which is processed by the membrane-bound terpene cyclase (TPC) AscF in AC biosynthesis. AF biosynthesis branches from the precursor by hydroxylation at C-16 by the P450 monooxygenase AscH, followed by cyclization by a membrane-bound TPC AscI. All genes required for AC biosynthesis (ascABCDEFG) and a transcriptional factor (ascR)

  Ascofuranone（AF）和Ascochlorin（AC）是由各种丝状真菌（包括埃及顶头孢霉（Acremonium sclerotigenum））产生的甲萜类化合物，并表现出多种生理活性。特别地，AF是抗非洲锥虫病的有前途的候选药物和潜在的抗癌先导化合物。据推测，这些化合物是通过奥数酸的法呢基化来生物合成的，但尚未确定细节。在这项研究中，我们介绍了埃及埃及曲霉的AF和AC生物合成的所有反应和负责任的基因通过异源表达，体外重建和基因缺失实验，借助全基因组差异表达分析进行鉴定。两种途径共有共同的前体，环氧化依里克林A，其通过膜结合的萜烯环化酶（TPC）AscF在AC生物合成中进行处理。AF生物合成通过P450单加氧酶AscH在C-16处的羟基化作用从前驱物分支，然后通过膜结合的TPC AscI进行环化。AC生物合成所需的所有基因（ascABCDEFG）和转录因子（ascR）形成功能性基因
• Biosynthesis of LL-Z1272β: Discovery of a New Member of NRPS-like Enzymes for Aryl-Aldehyde Formation
  作者：Chang Li、Yudai Matsuda、Hao Gao、Dan Hu、Xin Sheng Yao、Ikuro Abe

  DOI：10.1002/cbic.201600087

  日期：2016.5.17

  Unusual carboxylate reductase: The biosynthetic pathway of a prenylated aryl‐aldehyde, LL‐Z1272β (1), has been established. Interestingly, the last step in LL‐Z1272β biosynthesis involves a non‐ribosomal peptide synthetase (NRPS)‐like protein, StbB, which serves as a carboxylate reductase to yield the aldehyde functionality from a farnesylated substrate.

  异常的羧酸还原酶：已建立了烯丙基芳基醛LL-Z1272β（1）的生物合成途径。有趣的是，LL-Z1272β生物合成的最后一步涉及非核糖体肽合成酶（NRPS）样蛋白StbB，它充当羧酸还原酶从法呢基化底物产生醛官能团。