FMOC-(S)-3-氨基-4-(4-氯苯基)-丁酸 | 270596-43-5

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - FMOC-氨基酸
• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: FMOC-(S)-3-氨基-4-(4-氯苯基)-丁酸
• 英文名称: N-(9-fluorenylmethyloxycarbonyl)-L-β-homo-p-chlorophenylalanine
• 英文别名: (S)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-4-(4-chlorophenyl)butanoic acid；(3S)-4-(4-chlorophenyl)-3-(9H-fluoren-9-ylmethoxycarbonylamino)butanoic acid
• CAS: 270596-43-5
• 化学式: C₂₅H₂₂ClNO₄
• mdl: MFCD01861002
• 分子量: 435.907
• InChiKey: FMGGSUXYRDKFJX-SFHVURJKSA-N

物化性质

• 沸点：
  653.6±55.0 °C(Predicted)
• 密度：
  1.313±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 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：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 安全说明：
  S22,S24/25
• WGK Germany：
  3
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  FMOC-(S)-3-氨基-4-(4-氯苯基)-丁酸 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 3-[(S)-4-(4-Chloro-phenyl)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-butyrylamino]-propionic acid 4-[1-(4,4-dimethyl-2,6-dioxo-cyclohexylidene)-3-methyl-butylamino]-benzyl ester
  参考文献：
  名称：

  Solution phase synthesis of β-peptides using micro reactors

  摘要：

  The synthesis of beta-peptides has been successfully performed using a borosilicate glass micro reactor, in which a network of channels has been produced using a photolithographic and wet etching method. The reagents were mobilised by electroosmotic flow (EOF). The micro reactor was initially evaluated using a carbodiimide coupling reaction to form a dipeptide. The methodology has been extended such that the peptides may also be produced via the pentafluorophenyl ester derivatives of amino acids. It was found that performing the pentafluorophenyl ester reactions in the micro reactor resulted in an increase in the reaction efficiency over the traditional batch method. We postulate that the enhancement in rate of reaction is an electrochemical phenomenon, due to the reaction being performed in an electric field, which is unique to micro reactor systems. It has also been demonstrated that selective deprotection of the resultant dipeptides can be achieved. This approach has been used in the synthesis of a tripeptide. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00513-6
• 作为产物：
  描述：

  氯甲酸-9-芴基甲酯 、 (S)-3-氨基-4-(4-氯苯基)-丁酸盐酸盐 在 碳酸氢钠 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以70%的产率得到FMOC-(S)-3-氨基-4-(4-氯苯基)-丁酸
  参考文献：
  名称：

  Solution phase synthesis of β-peptides using micro reactors

  摘要：

  The synthesis of beta-peptides has been successfully performed using a borosilicate glass micro reactor, in which a network of channels has been produced using a photolithographic and wet etching method. The reagents were mobilised by electroosmotic flow (EOF). The micro reactor was initially evaluated using a carbodiimide coupling reaction to form a dipeptide. The methodology has been extended such that the peptides may also be produced via the pentafluorophenyl ester derivatives of amino acids. It was found that performing the pentafluorophenyl ester reactions in the micro reactor resulted in an increase in the reaction efficiency over the traditional batch method. We postulate that the enhancement in rate of reaction is an electrochemical phenomenon, due to the reaction being performed in an electric field, which is unique to micro reactor systems. It has also been demonstrated that selective deprotection of the resultant dipeptides can be achieved. This approach has been used in the synthesis of a tripeptide. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00513-6

文献信息

• Small molecule conjugates for intracellular delivery of nucleic acids
  申请人：Hoffmann-La Roche Inc.

  公开号：US20140135380A1

  公开（公告）日：2014-05-15

  The invention provides use of novel compounds for delivery of nucleic acids, and conjugates of these compounds with nucleic acids. Further novel design criteria for chemically stabilized siRNA particular useful when covalently attached to said compounds and co-administered with a delivery polymer to achieve mRNA knock down in vivo are disclosed therein.

  本发明提供了一种使用新化合物进行核酸传递的方法，并提供了这些化合物与核酸的结合物。此外，还揭示了一种新的设计标准，用于化学稳定的siRNA，当与该化合物共价结合并与传递聚合物共同给予时，可在体内实现mRNA靶向下调。
• Small molecule conjugates for intracellular delivery of biologically active compounds
  申请人：Hoffmann-La Roche Inc.

  公开号：US20140135381A1

  公开（公告）日：2014-05-15

  The invention provides novel compounds and conjugates of these compounds useful for the delivery of biologically active substances. Further novel design criteria for chemically stabilized siRNA particular useful when covalently attached to a delivery polymer to achieve in vivo mRNA knock down are disclosed therein.

  本发明提供了新型化合物及其共轭物，用于传递生物活性物质。本发明还揭示了化学稳定的siRNA的新设计标准，特别是当与传递聚合物共价连接以实现体内mRNA敲下时，这些标准非常有用。
• SMALL MOLECULE CONJUGATES FOR INTRACELLULAR DELIVERY OF BIOLOGICALLY ACTIVE COMPOUNDS
  申请人：F.Hoffmann-La Roche AG

  公开号：EP2658982B1

  公开（公告）日：2016-04-20
• US9198947B2
  申请人：——

  公开号：US9198947B2

  公开（公告）日：2015-12-01
• US9301990B2
  申请人：——

  公开号：US9301990B2

  公开（公告）日：2016-04-05