(3,5-Dichloro-2,4,6-trihydroxyphenyl)hexan-1-one(1-)

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3,5-Dichloro-2,4,6-trihydroxyphenyl)hexan-1-one(1-)
• 英文别名: 2,6-dichloro-4-hexanoyl-3,5-dihydroxyphenolate
• 化学式: C12H13Cl2O4-
• 分子量: 292.13
• InChiKey: WLWLDMLTAFSEDI-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  (3,5-Dichloro-2,4,6-trihydroxyphenyl)hexan-1-one(1-) 、 S-腺苷蛋氨酸 生成 1-(3,5-Dichloro-2,6-dihydroxy-4-methoxyphenyl)hexan-1-one(1-) 、 氢(+1)阳离子 、 S-(5'-腺苷)-L-高半胱氨酸
  参考文献：
  名称：

  The Biosynthesis of Differentiation-Inducing Factor, a Chlorinated Signal Molecule Regulating DictyosteliumDevelopment

  摘要：

  Differentiation-inducing factor (DIF)-1 is a chlorinated alkyl phenone released by developing Dictyostelium amoebae, which induces them to differentiate into stalk cells, A biosynthetic pathway for DIF-1 is proposed from labeling, inhibitor, and enzymological experiments, Cells incorporate Cl-36(-) into DIF-1 during development, showing that the chlorine atoms originate from chloride ions; peak incorporation is at the first finger stage, DIF-1 synthesis can be blocked by cerulenin, a polyketide synthase inhibitor, suggesting that it is made from a polyketide, This is most likely the C-12 polyketide (2,4,6-trihydroxyphenyl)-1-hexan-1-one (THPH). Feeding experiments confirm that living cells can convert THPH to DIF-1, Conversion requires both chlorination and methylation of THPH, and enzymatic activities able to do this exist in cell lysates, The chlorinating activity, assayed using Cl-36(-), is stimulated by H2O2 and requires both soluble and particulate components, It is specific for THPH and does not use this compound after O-methylation. The methyltransferase is soluble, uses S-adenosyl-L-methionine as a co-substrate, has a K-m for dichloro-THPH of about 1.1 mu M, and strongly prefers this substrate to close analogues, Both chlorinating and methyltransferase activities increase in development in parallel with DIF-1 production, and both are greatly reduced in a mutant strain that makes little DIF-1, It is proposed that DIF-1 is made by the initial assembly of a C-12 polyketide skeleton, which is then chlorinated and methylated.

  DOI：

  10.1074/jbc.273.5.2669
• 作为产物：
  描述：

  chloro-THPH(1-) 、 氯离子 、 10-[(2S,3S,4R)-5-[[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-2,3,4-trihydroxypentyl]-7,8-dimethyl-5H-benzo[g]pteridine-2,4-diolate 、 氧气 生成 (3,5-Dichloro-2,4,6-trihydroxyphenyl)hexan-1-one(1-) 、 FAD 、 水
  参考文献：
  名称：

  A flavin-dependent halogenase catalyzes the chlorination step in the biosynthesis of Dictyostelium differentiation-inducing factor 1

  摘要：

  诱导分化因子1（DIF-1）是一种由聚酮衍生的形态因子，在Dictyostelium discoideum的发育周期中促进茎细胞形成。先前的实验表明，生物合成途径通过对前体分子THPH的二氯化进行。但负责这一转化的酶尚未被表征。我们最近对原核黄酮依赖卤素酶的研究以及从已测序的Dd基因组中获得的见解，让我们找到了这一转化的候选基因。在这项工作中，我们提供了体内和体外证据，表明Dd中的chlA编码一种能够催化DIF-1生物合成中的两次氯化的黄酮依赖卤素酶。这些结果提供了一个关于真核氧依赖卤素酶的体外特征化，并展示了这种分子修饰策略在生物学中的广泛应用，尤其是在社会变形虫的分化程序中的参与。

  DOI：

  10.1073/pnas.1001681107