1-(3,5-Dichloro-2,6-dihydroxy-4-methoxyphenyl)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: 1-(3,5-Dichloro-2,6-dihydroxy-4-methoxyphenyl)hexan-1-one(1-)
• 英文别名: 2,4-dichloro-6-hexanoyl-5-hydroxy-3-methoxyphenolate
• 化学式: C13H15Cl2O4-
• 分子量: 306.16
• InChiKey: VUDQSRFCCHQIIU-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  69.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  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

文献信息

• The Biosynthesis of Differentiation-Inducing Factor, a Chlorinated Signal Molecule Regulating DictyosteliumDevelopment
  作者：Robert R. Kay

  DOI：10.1074/jbc.273.5.2669

  日期：1998.1

  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.