(R)-Fmoc-4-甲氧基-beta-苯丙氨酸 | 511272-33-6

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 苯丙氨酸类衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: (R)-Fmoc-4-甲氧基-beta-苯丙氨酸
• 中文别名: (R)-3-芴甲氧羰酰基氨基-3-(4-甲氧基苯基)丙酸；R-Fmoc-4-甲氧基-β-苯丙氨酸
• 英文名称: (R)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(4-methoxyphenyl)propanoic acid
• 英文别名: (3R)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(4-methoxyphenyl)propanoic acid
• CAS: 511272-33-6
• 化学式: C₂₅H₂₃NO₅
• 分子量: 417.461
• InChiKey: GXOCWIPOYXOZAF-HSZRJFAPSA-N

物化性质

• 沸点：
  648.9±55.0 °C(Predicted)
• 密度：
  1.273±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  (R)-Fmoc-4-甲氧基-beta-苯丙氨酸 、 Fmoc-L-丙氨酸 、 N-alpha-芴甲氧羰基-N-in-叔丁氧羰基-D-色氨酸 、 4-(芴甲氧羰基氨基)丁酸 生成 (3R,6R,9S)-18-amino-6-((1-(tert-butoxycarbonyl)-1H-indol-3-yl)methyl)-3-(4-methoxyphenyl)-9-methyl-5,8,11,15-tetraoxo-4,7,10,14-tetraazaoctadecanoic acid
  参考文献：
  名称：

  Synthetic and pharmacological studies on new simplified analogues of the potent actin-targeting Jaspamide

  摘要：

  In the recent years, we focused our attention on the cyclodepsipeptide Jaspamide 1, an interesting marine metabolite, possessing a potent inhibitory activity against breast and prostate cancer, as a consequence of its ability to disrupt actin cytoskeleton dynamics. Although its biological pro. le has been well determined, many mechanistic details are still missing in terms of molecular target identification. For this reason, we decided to synthetically modify the natural metabolite, obtaining small arrays of unnatural variants useful to illuminate the structural requirements essential for the activity. Here, we report the synthesis of seven new Jaspamide analogues 2-8, containing, as the parent compound, a beta-amino acid in the cyclopeptide backbone. Their biological pro. le is also described. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.05.019
• 作为产物：
  描述：

  氯甲酸-9-芴基甲酯 、 (R)-3-氨基-3-(4-甲氧基苯基)丙酸 在 sodium carbonate 作用下， 以 水 、 丙酮 为溶剂， 以69%的产率得到(R)-Fmoc-4-甲氧基-beta-苯丙氨酸
  参考文献：
  名称：

  Synthetic and pharmacological studies on new simplified analogues of the potent actin-targeting Jaspamide

  摘要：

  In the recent years, we focused our attention on the cyclodepsipeptide Jaspamide 1, an interesting marine metabolite, possessing a potent inhibitory activity against breast and prostate cancer, as a consequence of its ability to disrupt actin cytoskeleton dynamics. Although its biological pro. le has been well determined, many mechanistic details are still missing in terms of molecular target identification. For this reason, we decided to synthetically modify the natural metabolite, obtaining small arrays of unnatural variants useful to illuminate the structural requirements essential for the activity. Here, we report the synthesis of seven new Jaspamide analogues 2-8, containing, as the parent compound, a beta-amino acid in the cyclopeptide backbone. Their biological pro. le is also described. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.05.019