S-2-acetamidoethyl 7-((3R,5R)-3,5-dihydroxy-6-phenylhexanamido)heptanethioate | 1374151-49-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: S-2-acetamidoethyl 7-((3R,5R)-3,5-dihydroxy-6-phenylhexanamido)heptanethioate
• 英文别名: S-(2-acetamidoethyl) 7-[[(3R,5R)-3,5-dihydroxy-6-phenylhexanoyl]amino]heptanethioate
• CAS: 1374151-49-1
• 化学式: C₂₃H₃₆N₂O₅S
• 分子量: 452.615
• InChiKey: CWIXSPIQEYPECK-NHCUHLMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  31
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  141
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  S-2-acetamidoethyl 7-((3R,5R)-3,5-dihydroxy-6-phenylhexanamido)heptanethioate 在 6-deoxyerythronolide B synthase thioesterase 作用下， 以 二甲基亚砜 为溶剂， 反应 18.0h， 生成 2-benzyl-4-hydroxy-1-oxa-7-azacyclotetradecane-6,14-dione 、 7-((3R,5R)-3,5-dihydroxy-6-phenylhexanamido)heptanoic acid
  参考文献：
  名称：

  6-Deoxyerythronolide B Synthase Thioesterase-Catalyzed Macrocyclization Is Highly Stereoselective

  摘要：

  Macrocyclic polyketide natural products are an indispensable source of therapeutic agents. The final stage of their biosynthesis, macrocyclization, Is catalyzed regio- and stereoselectively by a thioesterase. A panel of substrates were synthesized to test their specificity for macrocyclization by the erythromycin polyketide synthase TE (DEBS TE) in vitro. It was shown that DEBS TE is highly stereospecific, successfully macrocyclizing a 14-member ring substrate with an R configured O-nucleophile, and highly regioselective, generating exclusively the 14-member lactone over the 12-member lactone.

  DOI：

  10.1021/ol300707j
• 作为产物：
  描述：

  7-氨基庚酸甲酯 在 吡啶 、 4-二甲氨基吡啶 、 氢氟酸 、 水 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 11.08h， 生成 S-2-acetamidoethyl 7-((3R,5R)-3,5-dihydroxy-6-phenylhexanamido)heptanethioate
  参考文献：
  名称：

  6-Deoxyerythronolide B Synthase Thioesterase-Catalyzed Macrocyclization Is Highly Stereoselective

  摘要：

  Macrocyclic polyketide natural products are an indispensable source of therapeutic agents. The final stage of their biosynthesis, macrocyclization, Is catalyzed regio- and stereoselectively by a thioesterase. A panel of substrates were synthesized to test their specificity for macrocyclization by the erythromycin polyketide synthase TE (DEBS TE) in vitro. It was shown that DEBS TE is highly stereospecific, successfully macrocyclizing a 14-member ring substrate with an R configured O-nucleophile, and highly regioselective, generating exclusively the 14-member lactone over the 12-member lactone.

  DOI：

  10.1021/ol300707j