dimethyl (4-(methoxymethoxy)-6-oxo-6H-pyran-2-yl)methylphosphonate | 922185-75-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: dimethyl (4-(methoxymethoxy)-6-oxo-6H-pyran-2-yl)methylphosphonate
• 英文别名: 6-[[Dimethoxy(oxido)phosphaniumyl]methyl]-4-(methoxymethoxy)pyran-2-one；6-[[dimethoxy(oxido)phosphaniumyl]methyl]-4-(methoxymethoxy)pyran-2-one
• CAS: 922185-75-9
• 化学式: C₁₀H₁₅O₇P
• 分子量: 278.199
• InChiKey: GVSIYXFDRVYRQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  86.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  dimethyl (4-(methoxymethoxy)-6-oxo-6H-pyran-2-yl)methylphosphonate 在 盐酸 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 36.0h， 生成 2-hydroxy-4-[(1E,3E,5E,7E)-3-methylnona-1,3,5,7-tetraen-1-yl]-2-pyranone
  参考文献：
  名称：

  Syntheses of Conjugated Pyrones for the Enzymatic Assay of Lovastatin Nonaketide Synthase, an Iterative Polyketide Synthase

  摘要：

  Lovastatin nonaketide synthase (LovB, LNKS) is an iterative type I polyketide synthase (PKS) from Aspergillus terreus that produces dihydromonacolin L (2), the biosynthetic precursor of lovastatin (1), from acetyl CoA, malonyl CoA, and S-adenosylmethionine (SAM) if the accessory protein LovC is present. In the absence of LovC, LNKS forms the conjugated pyrones 3 and 4 as truncated PKS products. Short syntheses of these pyrones provide material for the assay of LNKS activity by HPLC and radioisotope dilution analysis.

  DOI：

  10.1021/ol062763i
• 作为产物：
  描述：

  4-(methoxymethoxy)-6-methyl-2H-pyran-2-one 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 作用下， 以 四氯化碳 为溶剂， 反应 36.0h， 生成 dimethyl (4-(methoxymethoxy)-6-oxo-6H-pyran-2-yl)methylphosphonate
  参考文献：
  名称：

  Syntheses of Conjugated Pyrones for the Enzymatic Assay of Lovastatin Nonaketide Synthase, an Iterative Polyketide Synthase

  摘要：

  Lovastatin nonaketide synthase (LovB, LNKS) is an iterative type I polyketide synthase (PKS) from Aspergillus terreus that produces dihydromonacolin L (2), the biosynthetic precursor of lovastatin (1), from acetyl CoA, malonyl CoA, and S-adenosylmethionine (SAM) if the accessory protein LovC is present. In the absence of LovC, LNKS forms the conjugated pyrones 3 and 4 as truncated PKS products. Short syntheses of these pyrones provide material for the assay of LNKS activity by HPLC and radioisotope dilution analysis.

  DOI：

  10.1021/ol062763i

文献信息

• Enzymatic Synthesis of Resorcylic Acid Lactones by Cooperation of Fungal Iterative Polyketide Synthases Involved in Hypothemycin Biosynthesis
  作者：Hui Zhou、Kangjian Qiao、Zhizeng Gao、Michael J. Meehan、Jesse W.-H. Li、Xiling Zhao、Pieter C. Dorrestein、John C. Vederas、Yi Tang

  DOI：10.1021/ja100060k

  日期：2010.4.7

  Hypothemycin is a macrolide protein kinase inhibitor from the fungus Hypomyces subiculosus. During biosynthesis, its carbon framework is assembled by two iterative polyketide synthases (PKSs), Hpm8 (highly reducing) and Hpm3 (nonreducing). These were heterologously expressed in Saccharomyces cerevisiae BJ5464-NpgA, purified to near homogeneity, and reconstituted in vitro to produce (6'S,10'S)-trans-7'

  Hypothemycin 是一种来自真菌 Hypomyces subiculosus 的大环内酯蛋白激酶抑制剂。在生物合成过程中，其碳框架由两个迭代聚酮合酶 (PKS)、Hpm8（高度还原）和 Hpm3（非还原）组装而成。它们在酿酒酵母 BJ5464-NpgA 中异源表达，纯化至接近同质，并在体外重组以从丙二酰辅酶 A 和 NADPH 生产 (6'S,10'S)-反式-7',8'-脱氢玉米赤霉烯醇 (1)。1的结构是通过X射线晶体学分析确定的。在没有功能性 Hpm3 的情况下，还原性 PKS Hpm8 会产生并卸载截短的吡喃酮产物，而不是预期的六酮化合物。非还原性 Hpm3 能够接受正确官能化的六酮化合物的 N-乙酰半胱胺硫酯以形成 1，但它不能启动丙二酰辅酶A 形成聚酮化合物。我们表明 Hpm3 的起始单元：ACP 转酰基酶 (SAT) 对两种酶之间的串扰至关重要，并且 1 的生物合成速率由
• Syntheses of Conjugated Pyrones for the Enzymatic Assay of Lovastatin Nonaketide Synthase, an Iterative Polyketide Synthase
  作者：Douglas A. Burr、Xuan B. Chen、John C. Vederas

  DOI：10.1021/ol062763i

  日期：2007.1.1

  Lovastatin nonaketide synthase (LovB, LNKS) is an iterative type I polyketide synthase (PKS) from Aspergillus terreus that produces dihydromonacolin L (2), the biosynthetic precursor of lovastatin (1), from acetyl CoA, malonyl CoA, and S-adenosylmethionine (SAM) if the accessory protein LovC is present. In the absence of LovC, LNKS forms the conjugated pyrones 3 and 4 as truncated PKS products. Short syntheses of these pyrones provide material for the assay of LNKS activity by HPLC and radioisotope dilution analysis.