2-trifluoroacetamidobutanedioic acid | 369-08-4

• 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
• 英文名称: 2-trifluoroacetamidobutanedioic acid
• 英文别名: N-trifluoroacetyl-L-aspartic acid；N-Trifluoracetyl-aminobernsteinsaeure；L-Asparaginsaeure-N-trifluoracetat；N-Trifluoracetyl-L-asparaginsaeure；N-(2,2,2-Trifluoroacetyl)-L-aspartic acid；(2S)-2-[(2,2,2-trifluoroacetyl)amino]butanedioic acid
• CAS: 369-08-4
• 化学式: C₆H₆F₃NO₅
• 分子量: 229.113
• InChiKey: NTFULCXLYCSQIW-REOHCLBHSA-N

物化性质

• 沸点：
  350.3±42.0 °C(Predicted)
• 密度：
  1.641±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  L-苯丙氨酸甲酯盐酸盐 、 2-trifluoroacetamidobutanedioic acid 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 、 三乙胺 作用下， 以 乙酸乙酯 为溶剂， 反应 2.5h， 生成 N-trifluoroacetyl-L-aspartyl-L-phenylalanine
  参考文献：
  名称：

  直接，可见光敏化的苄基C H氟化使用二苯并顺丁烯二酮：对苯丙氨酸样残基的选择性

  摘要：

  可见光敏化苄SP 3 Ç ħ氟化使用dibenzosuberenone（5摩尔％）和的Selectfluor协议®为苯丙氨酸样在短链肽的残基的直接官能优化。在受保护的碱性，酸性和非极性侧链（包括具有叔位的侧链）存在下，氨基酸，二肽和三肽会经历显着的区域选择性的苄基氟化反应。此外，还探讨了保护基团的兼容性，克规模应用和竞争实验。

  DOI：

  10.1016/j.tet.2016.08.018
• 作为产物：
  描述：

  (S)-(-)-2-(三氟乙酰胺)琥珀酸酐 在 水 作用下， 生成 2-trifluoroacetamidobutanedioic acid
  参考文献：
  名称：

  Weygand,F.; Fritz,H., Chemische Berichte, 1965, vol. 98, p. 72 - 82

  摘要：

  DOI：

文献信息

• Effect of N-Trifluoroacetyl Derivatives of Amino Acids and Amino Acid Analogs on Microbial Antitumor Screen
  作者：Theodore T. Otani、Mary R. Briley

  DOI：10.1002/jps.2600680428

  日期：1979.4

  Eighteen trifluoroacetyl derivatives of amino acids and of amino acid analogs were prepared and tested for growth-inhibitory activity using a Lactobacillus casei system as a prescreen for antitumor activity. Of the compounds tested, the trifluoroacetyl derivatives of o-, m-, and p-fluorophenylalanine and of beta-3-thienylalanine showed modest activity; trifluoroacetyl derivatives of phenylalanine and of

  制备了十八种氨基酸和氨基酸类似物的三氟乙酰基衍生物，并使用干酪乳杆菌系统作为抗肿瘤活性的预筛测试了其生长抑制活性。在所测试的化合物中，邻，间和对氟苯基丙氨酸和β-3-噻吩丙氨酸的三氟乙酰基衍生物显示出适度的活性。苯丙氨酸和β-2-噻吩丙氨酸的三氟乙酰基衍生物显示边缘活性。活性三氟乙酰基化合物表现出的活性与先前报道的大多数活性氯乙酰基衍生物所指出的活性相同，这是通过将它们与氯乙酰基-间-氟苯丙氨酸的活性进行比较来判断的。当这些抑制剂的代表用相应的天然代谢物挑战时，没有发现抑制作用的逆转，
• Azacycloalkane derivatives as inhibitors of stearoyl-coenzyme a delta-9 desaturase
  申请人：Lachance Nicolas

  公开号：US20080132542A1

  公开（公告）日：2008-06-05

  Azacycloalkane derivatives of structural formula I are selective inhibitors of stearoyl-coenzyme A delta-9 desaturase (SCD1) relative to other known stearoyl-coenzyme A desaturases. The compounds of the present invention are useful for the prevention and treatment of conditions related to abnormal lipid synthesis and metabolism, including cardiovascular disease, such as atherosclerosis; obesity; diabetes; neurological disease; metabolic syndrome; insulin resistance; and liver steatosis.

  结构式I的氮代环烷衍生物是选择性抑制剂，相对于其他已知的硬脂酰辅酶A delta-9去饱和酶（SCD1）。本发明的化合物可用于预防和治疗与异常脂质合成和代谢相关的疾病，包括心血管疾病，如动脉粥样硬化；肥胖；糖尿病；神经系统疾病；代谢综合征；胰岛素抵抗；和肝脂肪变性。
• Molecular Design of Fluorescent Labeled Glycosides as Acceptor Substrates for Sialyltransferases
  作者：Makoto OGATA、Takakiyo OBARA、Yasushi CHUMA、Takeomi MURATA、Enoch Y. PARK、Taichi USUI

  DOI：10.1271/bbb.100505

  日期：2010.11.23

  A series of dansyl-labeled glycosides with di-, tetra-, and hexasaccharides carrying the terminal N-acetyllactosamine (LacNAc) sequence were synthesized as acceptor substrates for α2,6- and α2,3-sialyltransferases. As an alternative design, dansyl-labeled LacNAc glycoside carrying a long-spacer linked glycan was engineered by replacement of the LacNAc or lactose units with an alkyl chain. In addition, we designed a dansyl-labeled bi-antennary LacNAc glycoside as an N-linked oligosaccharide mimetic, such as asialo-α1-acid glycoprotein. The kinetic parameters for the transfer reaction of synthesized dansyl-labeled glycosides by sialyltransferases were determined by the fluorescent HPLC method. The catalytic efficiencies (V  max/K  m) of acceptor substrates carrying the terminal LacNAc sequence with various length glycans in the array for α2,6- and α2,3-sialyltransferases decreased in a glycan length-dependent manner. Furthermore, of the acceptor substrates tested, dansyl-labeled bi-antennary LacNAc glycoside displayed the most favorable K  m value for α2,6- and α2,3-sialyltransferases.

  一系列带有终端N-乙酰乳糖胺（LacNAc）序列的二糖、四糖和六糖的丹酰标记糖苷被合成为α2,6-和α2,3-唾液酸转移酶的受体底物。作为替代设计，通过用烷基链替换LacNAc或乳糖单元，开发了一种带有长间隔链接糖的丹酰标记LacNAc糖苷。此外，我们设计了一种丹酰标记的双抗体LacNAc糖苷，作为N-linked寡糖的模拟物，例如非唾液酸α1-酸性糖蛋白。采用荧光HPLC方法确定了合成的丹酰标记糖苷在唾液酸转移酶转移反应中的动力学参数。对于携带终端LacNAc序列的受体底物，其在不同长度糖链中的催化效率（V_max/K_m）呈现出依赖于糖链长度的下降趋势。此外，在测试的受体底物中，丹酰标记的双抗体LacNAc糖苷对α2,6-和α2,3-唾液酸转移酶显示出最有利的K_m值。
• Preparation of N-protected .alpha.-L-aspartyl-L-phenylalanine methyl
  申请人：Mitsui Toatsu Chemicals, Inc.

  公开号：US05302743A1

  公开（公告）日：1994-04-12

  Disclosed is an improved process for the preparation of an N-protected .alpha.-L-aspartyl-L-phenylalanine methyl ester from an N-protected L-aspartic anhydride and L-phenylalanine methyl ester, the improvement which comprises employing the L-phenylalanine methyl ester in the form of a mineral acid salt thereof and conducting the reaction either (a) in an organic solvent and in the presence of a salt of an organic carboxylic acid, or (b) in an organic solvent comprising an organic carboxylic acid and in the presence of at least one member of the group consisting of an alkali metal or an alkaline earth metal inorganic base, an ammonium alkali metal or alkaline earth metal salt of an organic carboxylic acid and ammonium carbonate. The starting N-protected aspartic anhydride, e.g., N-benzyloxycarbonyl-L-aspartic anhydride, can be produced by the reaction of N-protected aspartic acid with phosgene. When the N-protecting group sibenzyloxycarbonyl and the solvent is acetic acid, the desired product can be isolated from the reaction mixture in crystalline form in high purity by adding water thereto.

  本发明公开了一种改进的方法，用于从N-保护的L-天冬氨酸酐和L-苯丙氨酸甲酯制备N-保护的α-L-天冬氨酸-L-苯丙氨酸甲酯，其改进包括采用以矿酸盐形式存在的L-苯丙氨酸甲酯，并在有机溶剂中进行反应，同时存在有机羧酸盐的盐类（a），或在包含有机羧酸的有机溶剂中进行反应，并存在于由碱金属或碱土金属无机碱、有机羧酸的铵盐和碳酸铵组成的至少一个成员的存在下（b）。起始的N-保护的天冬氨酸酐，例如N-苄氧羰基-L-天冬氨酸酐，可以通过N-保护的天冬氨酸与光气反应而产生。当N-保护基为苄氧羰基且溶剂为乙酸时，可以通过添加水从反应混合物中以结晶形式高纯度地分离所需的产物。
• L-aspartyl amide derivatives and their use as sweetening agents
  申请人：THE PROCTER & GAMBLE COMPANY

  公开号：EP0013044A1

  公开（公告）日：1980-07-09

  L-1-hydroxymethy) alkaneamide derivatives of-L- aspartic acid have been prepared and have been discovered to be non-nutritive sweeteners having favorable chemical and physiological properties for use in compositions ingested orally. The compounds have the general formula wherein R1 = R2 = H or CH3; R3 = H or CH3; and R' = CH3, C2H5, i - C3H7 or t-C4H9; except that where R4 is i-C3H or t-C4H9, R2 and R3 are H.

  现已制备出 L-天冬氨酸的 L-1-羟甲基烷酰胺衍生物，并发现这种衍生物是一种非营养性甜味剂，具有良好的化学和生理特性，可用于口服组合物中。这些化合物的通式为 其中 R1 = R2＝H或CH3；R3＝H或CH3；R'＝CH3、C2H5、i-C3H7或t-C4H9；但当R4为i-C3H或t-C4H9时，R2和R3为H。