(2E,10E)-hexadeca-2,10-diene-1,9-diolide | 128677-31-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2E,10E)-hexadeca-2,10-diene-1,9-diolide
• 英文别名: (3E,12E)-1,10-dioxacyclooctadeca-3,12-diene-2,11-dione
• CAS: 128677-31-6；128693-42-5
• 化学式: C₁₆H₂₄O₄
• 分子量: 280.364
• InChiKey: ZHMLYAGXWSJKCP-MKICQXMISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.32
• 重原子数：
  20.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  6-(tetrahydro-2H-pyranyloxy)hexan-1-ol 在 草酰氯 、 VinP₄ polyketide synthase thioesterase domain 、 sodium hydride 、 对甲苯磺酸 、 二甲基亚砜 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 29.08h， 生成 (2E,10E,18E)-tetracosa-2,10,18-triene-1,9,17-triolide 、 (2E,10E)-hexadeca-2,10-diene-1,9-diolide
  参考文献：
  名称：

  Potent Oligomerization and Macrocyclization Activity of the Thioesterase Domain of Vicenistatin Polyketide Synthase

  摘要：

  The thioesterase domain of the polyketide synthase involved in the biosynthesis of the 20-membered macrolactam antibiotic vicenistatin (VinTE) was found to catalyze oligomerization and macrocyclization of omega-hydroxy fatty acid ethyl esters to afford 17-28-membered macrocyclic lactones. The ring sizes of the macrocycles appear to be limited to the more moderate sizes because of the space limitation of the active site of VinTE. It was also verified that the initially formed linear dimer is first released from the active site of VinTE and then is recognized again by VinTE prior to its transformation to the cyclic dimer.

  DOI：

  10.1055/s-0031-1290385

文献信息

• Floc'h, Y. Le; Yvergnaux, F.; Toupet, L., Bulletin de la Societe Chimique de France, 1991, # 5, p. 742 - 759
  作者：Floc'h, Y. Le、Yvergnaux, F.、Toupet, L.、Gree, R.

  DOI：——

  日期：——
• Potent Oligomerization and Macrocyclization Activity of the Thioesterase Domain of Vicenistatin Polyketide Synthase
  作者：Tadashi Eguchi、Fumitaka Kudo、Yusaku Asou、Moe Watanabe、Takashi Kitayama

  DOI：10.1055/s-0031-1290385

  日期：2012.7

  The thioesterase domain of the polyketide synthase involved in the biosynthesis of the 20-membered macrolactam antibiotic vicenistatin (VinTE) was found to catalyze oligomerization and macrocyclization of omega-hydroxy fatty acid ethyl esters to afford 17-28-membered macrocyclic lactones. The ring sizes of the macrocycles appear to be limited to the more moderate sizes because of the space limitation of the active site of VinTE. It was also verified that the initially formed linear dimer is first released from the active site of VinTE and then is recognized again by VinTE prior to its transformation to the cyclic dimer.