(S)?-?2-氨基-4,4-二氟丁酸 | 121960-22-3

• 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
• 中文名称: (S)?-?2-氨基-4,4-二氟丁酸
• 英文名称: (2S)-2-amino-4,4-difluorobutanoic acid
• 英文别名: L-difluoroAbu；α-amino-γ,γ-difluorobutyrate；(S)-2-amino-4,4-difluorobutyric acid；DfeGly；(2S)-2-azaniumyl-4,4-difluorobutanoate
• CAS: 121960-22-3
• 化学式: C₄H₇F₂NO₂
• 分子量: 139.102
• InChiKey: VIUCNIMDPZQXAD-REOHCLBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  苯甲氧羰酰琥珀酰亚胺 、 (S)?-?2-氨基-4,4-二氟丁酸 在 sodium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 (2S)-2-{[(benzyloxy)carbonyl]amino}-4,4-difluorobutanoic acid
  参考文献：
  名称：

  Phenethyl Amides as Novel Noncovalent Inhibitors of Hepatitis C Virus NS3/4A Protease:  Discovery, Initial SAR, and Molecular Modeling

  摘要：

  The discovery of novel, reversible and competitive tripeptide inhibitors of the Hepatitis C virus NS3/4A serine protease is described. These inhibitors are characterized by the presence of a C-terminal phenethyl amide group, which extends into the prime side of the enzyme. Initial SAR together with molecular modeling and data from site-directed mutagenesis suggest an interaction of the phenethyl amide group with Lys-136.

  DOI：

  10.1021/jm025594q
• 作为产物：
  描述：

  (S)-4-(2,2-Difluoro-ethyl)-2,2-bis-trifluoromethyl-oxazolidin-5-one 在 水 作用下， 以 异丙醇 为溶剂， 反应 168.0h， 以89%的产率得到(S)?-?2-氨基-4,4-二氟丁酸
  参考文献：
  名称：

  Synthesis of Enantiomerically Pure D- and L-Armentomycin and Its Difluoro Analogues from Aspartic Acid

  摘要：

  介绍了通过六氟丙酮保护的 2-氨基-4-氧代丁酸从天冬氨酸合成 2-氨基-4,4-二氯丁酸（安霉素）的两种对映体及其氟类似物。

  DOI：

  10.1055/s-1996-4409

文献信息

• Chemical aminoacylation of tRNAs with fluorinated amino acids for in vitro protein mutagenesis
  作者：Shijie Ye、Allison Ann Berger、Dominique Petzold、Oliver Reimann、Benjamin Matt、Beate Koksch

  DOI：10.3762/bjoc.6.40

  日期：——

  This article describes the chemical aminoacylation of the yeast phenylalanine suppressor tRNA with a series of amino acids bearing fluorinated side chains via the hybrid dinucleotide pdCpA and ligation to the corresponding truncated tRNA species. Aminoacyl-tRNAs can be used to synthesize biologically relevant proteins which contain fluorinated amino acids at specific sites by means of a cell-free translation system. Such engineered proteins are expected to contribute to our understanding of discrete fluorines’ interaction with canonical amino acids in a native protein environment and to enable the design of fluorinated proteins with arbitrary desired properties.

  本文描述了使用含有氟代侧链的一系列氨基酸通过杂交二核苷酸pdCpA化学氨酰化酵母苯丙氨酸抑制子tRNA，并与相应的截短tRNA物种连接。氨酰-tRNA可以用于通过无细胞翻译系统在特定位点合成含有氟代氨基酸的生物学相关蛋白质。这种工程蛋白质有望为我们了解离散氟元素在天然蛋白质环境中与基本氨基酸的相互作用以及设计具有任意所需特性的氟化蛋白质做出贡献。
• Phe*-Ala-based pentapeptide mimetics are BACE inhibitors: P2 and P3 SAR
  作者：Jason Lamar、Jingdan Hu、Ana Belen Bueno、Hsiu-Chiung Yang、Deqi Guo、James D. Copp、James McGee、Bruce Gitter、David Timm、Patrick May、James McCarthy、Shu-Hui Chen

  DOI：10.1016/j.bmcl.2003.09.084

  日期：2004.1

  We describe herein the syntheses and evaluation of a series of C-termini pyridyl containing Phe*-Ala-based BACE inhibitors (5-19). In conjunction with four fixed residues at the P1 (Phe), P1' (Ala), P2' (Val), and P2' cap (Pyr.), rather detailed SAR modifications at P2 and P3 positions were pursued. The promising inhibitors emerging from this SAR investigation, 12 and 17 demonstrated very good enzyme potency (IC50 = 45 nM) and cellular activity (IC50 = 0.4 muM). (C) 2003 Elsevier Ltd. All rights reserved.
• Phenethyl Amides as Novel Noncovalent Inhibitors of Hepatitis C Virus NS3/4A Protease:  Discovery, Initial SAR, and Molecular Modeling
  作者：Stefania Colarusso、Uwe Koch、Benjamin Gerlach、Christian Steinkühler、Raffaele De Francesco、Sergio Altamura、Victor G. Matassa、Frank Narjes

  DOI：10.1021/jm025594q

  日期：2003.1.1

  The discovery of novel, reversible and competitive tripeptide inhibitors of the Hepatitis C virus NS3/4A serine protease is described. These inhibitors are characterized by the presence of a C-terminal phenethyl amide group, which extends into the prime side of the enzyme. Initial SAR together with molecular modeling and data from site-directed mutagenesis suggest an interaction of the phenethyl amide group with Lys-136.
• Synthesis of Enantiomerically Pure D- and L-Armentomycin and Its Difluoro Analogues from Aspartic Acid
  作者：Dirk Winkler、Klaus Burger

  DOI：10.1055/s-1996-4409

  日期：1996.12

  The synthesis of both enantiomers of 2-amino-4,4-dichlorobutanoic acid (armentomycin) and their fluoro analogues from aspartic acid via 2-amino-4-oxobutanoic acid protected with hexafluoroacetone is described.

  介绍了通过六氟丙酮保护的 2-氨基-4-氧代丁酸从天冬氨酸合成 2-氨基-4,4-二氯丁酸（安霉素）的两种对映体及其氟类似物。