methyl (R)-3-(3,4-dimethoxybenzyloxy)-2-[(2Z,6E,13E)-3,8,8,14,18-pentamethyl-11-methylenenonadeca-2,6,13,17-tertaen-1-yloxy]propanoate | 916045-30-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: methyl (R)-3-(3,4-dimethoxybenzyloxy)-2-[(2Z,6E,13E)-3,8,8,14,18-pentamethyl-11-methylenenonadeca-2,6,13,17-tertaen-1-yloxy]propanoate
• 英文别名: methyl (R)-3-(3,4-dimethoxybenzyloxy)-2-[(2Z,6E,13E)-3,8,8,14,18-pentamethyl-11-methylene-nonadeca-2,6,13,17-tetraen-1-yloxy]-propanoate；methyl (2R)-3-[(3,4-dimethoxyphenyl)methoxy]-2-[(2Z,6E,13E)-3,8,8,14,18-pentamethyl-11-methylidenenonadeca-2,6,13,17-tetraenoxy]propanoate
• CAS: 916045-30-2
• 化学式: C₃₈H₅₈O₆
• 分子量: 610.875
• InChiKey: XCKUJJFKWAJJBN-VWADHVQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.5
• 重原子数：
  44
• 可旋转键数：
  23
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (R)-3-(3,4-dimethoxybenzyloxy)-2-[(2Z,6E,13E)-3,8,8,14,18-pentamethyl-11-methylenenonadeca-2,6,13,17-tertaen-1-yloxy]propanoate 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 phosphate buffer 、 二氯甲烷 为溶剂， 反应 1.0h， 以34%的产率得到methyl (R)-3-hydroxy-2-[(2Z,6E,13E)-3,8,8,14,18-pentamethyl-11-methylenenonadeca-2,6,13,17-tertaen-1-yloxy]propanoate
  参考文献：
  名称：

  Degradation and Reconstruction of Moenomycin A and Derivatives:  Dissecting the Function of the Isoprenoid Chain

  摘要：

  Moenomycin A is the only known natural product that inhibits peptidoglycan biosynthesis by binding the bacterial transglycosylases. We describe a degradation/reconstruction route to manipulate the reducing end of moenomycin A. A comparison of the biological and enzyme inhibitory activity of moenomycin A and an analogue containing a nerol lipid in place of the natural C25 lipid chain provides insight into the role of the moenocinol unit. Our results show that a lipid chain having ten carbons in moenocinol is sufficient for enzyme inhibition, but a longer chain is required for biological acitivity, apparently because the molecule must partition into biological membranes to reach its target in bacterial cells.

  DOI：

  10.1021/ja065905c
• 作为产物：
  描述：

  3,4-二甲氧基苄醇 在 chiral bis(iminophenoxy)-functionalized oligomer sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 、 四丁基氟化铵 、 sodium hydride 、 碳酸氢钠 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 、 叔丁醇 为溶剂， 反应 41.0h， 生成 methyl (R)-3-(3,4-dimethoxybenzyloxy)-2-[(2Z,6E,13E)-3,8,8,14,18-pentamethyl-11-methylenenonadeca-2,6,13,17-tertaen-1-yloxy]propanoate
  参考文献：
  名称：

  Degradation and Reconstruction of Moenomycin A and Derivatives:  Dissecting the Function of the Isoprenoid Chain

  摘要：

  Moenomycin A is the only known natural product that inhibits peptidoglycan biosynthesis by binding the bacterial transglycosylases. We describe a degradation/reconstruction route to manipulate the reducing end of moenomycin A. A comparison of the biological and enzyme inhibitory activity of moenomycin A and an analogue containing a nerol lipid in place of the natural C25 lipid chain provides insight into the role of the moenocinol unit. Our results show that a lipid chain having ten carbons in moenocinol is sufficient for enzyme inhibition, but a longer chain is required for biological acitivity, apparently because the molecule must partition into biological membranes to reach its target in bacterial cells.

  DOI：

  10.1021/ja065905c

文献信息

• MOENOMYCIN ANALOGS, METHODS OF SYNTHESIS, AND USES THEREOF
  申请人：Kahne Daniel

  公开号：US20110136759A1

  公开（公告）日：2011-06-09

  The present invention provides novel moenomycin analogs as well as pharmaceutical compositions thereof, methods of synthesis, and methods of use in treating an infection by administering an inventive compound to a subject in need thereof. The moenomycin analogs may be prepared synthetically, biosynthetically, or semi-synthetically. The analogs are particularly useful in treating or preventing infections caused by Gram-positive organisms. Certain inventive compounds may have a broader spectrum of coverage, which includes Gram-negative organisms.

  本发明提供了新型的莫诺霉素类似物及其制药组合物，合成方法以及将创新化合物用于治疗感染的方法，通过将创新化合物给予需要治疗的受试者来治疗感染。莫诺霉素类似物可以通过化学合成，生物合成或半合成的方式制备。这些类似物在治疗或预防由革兰氏阳性菌引起的感染中特别有用。某些创新化合物可能具有更广泛的覆盖范围，包括革兰氏阴性菌。
• Moenomycin analogs, methods of synthesis, and uses thereof
  申请人：Kahne Daniel

  公开号：US08604004B2

  公开（公告）日：2013-12-10

  The present invention provides novel moenomycin analogs as well as pharmaceutical compositions thereof, methods of synthesis, and methods of use in treating an infection by administering an inventive compound to a subject in need thereof. The moenomycin analogs may be prepared synthetically, biosynthetically, or semi-synthetically. The analogs are particularly useful in treating or preventing infections caused by Gram-positive organisms. Certain inventive compounds may have a broader spectrum of coverage, which includes Gram-negative organisms.

  本发明提供了新型莫诺霉素类似物及其药物组成物，合成方法和治疗感染的使用方法，通过向需要的受体中投与创新化合物来治疗感染。莫诺霉素类似物可以通过化学合成、生物合成或半合成方法制备。这些类似物特别适用于治疗或预防由革兰氏阳性菌引起的感染。某些创新化合物可能具有更广泛的覆盖范围，包括革兰氏阴性菌。
• [EN] MOENOMYCIN ANALOGS, METHODS OF SYNTHESIS, AND USES THEREOF<br/>[FR] ANALOGUES DE LA MOÉNOMYCINE, PROCÉDÉS DE SYNTHÈSE ET UTILISATIONS DE CEUX-CI
  申请人：HARVARD COLLEGE

  公开号：WO2009046314A3

  公开（公告）日：2009-05-22
• Degradation and Reconstruction of Moenomycin A and Derivatives:  Dissecting the Function of the Isoprenoid Chain
  作者：Masaatsu Adachi、Yi Zhang、Catherine Leimkuhler、Binyuan Sun、John V. LaTour、Daniel E. Kahne

  DOI：10.1021/ja065905c

  日期：2006.11.1

  Moenomycin A is the only known natural product that inhibits peptidoglycan biosynthesis by binding the bacterial transglycosylases. We describe a degradation/reconstruction route to manipulate the reducing end of moenomycin A. A comparison of the biological and enzyme inhibitory activity of moenomycin A and an analogue containing a nerol lipid in place of the natural C25 lipid chain provides insight into the role of the moenocinol unit. Our results show that a lipid chain having ten carbons in moenocinol is sufficient for enzyme inhibition, but a longer chain is required for biological acitivity, apparently because the molecule must partition into biological membranes to reach its target in bacterial cells.