β-benzyl-L-aspartic acid amide trifluoroacetate | 92762-94-2

• 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: β-benzyl-L-aspartic acid amide trifluoroacetate
• 英文别名: H-Asp(OBzl)-NH2 trifluoroacetate；TFA*Asp(OBzl)-NH2；benzyl (3S)-3,4-diamino-4-oxobutanoate;2,2,2-trifluoroacetic acid
• CAS: 92762-94-2
• 化学式: C₂HF₃O₂*C₁₁H₁₄N₂O₃
• 分子量: 336.268
• InChiKey: GWYINGZAJZJMRO-FVGYRXGTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.57
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  132.71
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N-Boc-L-正亮氨酸 、 β-benzyl-L-aspartic acid amide trifluoroacetate 在 N-甲基吗啉 、 N,N-二异丙基乙胺 、 氯甲酸异丁酯 作用下， 生成 Boc-L-Nle-L-Asp(Bzl)-NH2
  参考文献：
  名称：

  胆囊收缩素的一些部分修饰的逆反类似物的合成和生物学活性。

  摘要：

  描述了胆囊收缩素的C末端八肽或七肽的一些部分修饰的逆反类似物的合成。这些类似物（其中C-末端羧酰胺被缺失或未被缺失）是通过还原母体分子中的一个或几个肽键而获得的。所有这些化合物都能够抑制标记的CCK-8与大鼠胰腺腺泡和豚鼠脑膜的结合，并以各种效力刺激从大鼠胰腺腺泡释放的淀粉酶。这些衍生物中的一些仅在淀粉酶释放时再现CCK的生物学反应的一部分。

  DOI：

  10.1021/jm00130a018
• 作为产物：
  描述：

  Boc-L-天冬氨酸 4-苄酯 在 ammonium hydroxide 、 三乙胺 、 氯甲酸异丁酯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 β-benzyl-L-aspartic acid amide trifluoroacetate
  参考文献：
  名称：

  Synthesis, anti-inflammatory and antimicrobial activities of new 1,2,4-oxadiazoles peptidomimetics

  摘要：

  A new series of 1,2,4-oxadizoles 6a-g have been synthesised in good yields using the peptide synthesis strategy. The prepared compounds were tested for anti-inflammatory and antimicrobial activities. The anti-inflammatory activities were determined in the rat paw oedema induced by carrageenin. Compounds 6a, c, f and g (i.v.) significantly inhibited the rat paw oedema induced by carrageenin depending upon the dose employed. The compounds were also evaluated for their in vitro antimicrobial activity. Some compounds were found to have significant activity against Gram positive and Gram negative microorganisms. (C) 2000 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(00)00099-9

文献信息

• Boc-Trp-Orn(Z)-Asp-NH2 and derivatives: a new family of CCK antagonists
  作者：R. Gonzalez-Muniz、F. Bergeron、I. Marseigne、C. Durieux、Bernard P. Roques

  DOI：10.1021/jm00174a016

  日期：1990.12

  (Z) and of the N-terminal tripeptide moiety in the antagonist properties of the cholecystokinin CCK8 analogue Boc-[Nle28,Orn(Z)31]CCK27-33 (Marseigne et al. J. Med. Chem. 1988, 31, 966.) were studied with the following derivatives: Boc-[Nle28,Orn(X)31]CCK27-33, Boc[Nle28,Orn(X)31]CCK27-32, Boc-[Orn(X)31]CCK30-33, and Boc-[Orn(X)31]CCK30-32 (X = Z, Boc, H). These derivatives, the synthesis of eight of

  苄氧羰基（Z）和N端三肽部分在胆囊收缩素CCK8类似物Boc- [Nle28，Orn（Z）31] CCK27-33的拮抗特性中的各自作用（Marseigne et al.J.Med。 Chem。1988，31，966.）研究了以下衍生物：Boc- [Nle28，Orn（X）31] CCK27-33，Boc [Nle28，Orn（X）31] CCK27-32，Boc- [Orn（ X）31] CCK30-33和Boc- [Orn（X）31] CCK30-32（X = Z，Boc，H）。测试了这些衍生物的合成，此处报道了其中的八种衍生物的合成，以测试它们抑制[3H] pCCK8与豚鼠胰腺和脑膜结合的能力，以及刺激豚鼠胰腺痤疮淀粉酶释放的能力。Z衍生物均不产生淀粉酶分泌，但它们竞争性拮抗CCK8诱导的刺激。N末端三肽和/或Phe-NH2（33）残基的缺失在识别外周受体和这些肽的活性中不发挥关键作
• 2-Amino-4-pyrrolidinothieno[2,3-<i>d</i>]pyrimidine-6-carboxylic Acid as an<i>N</i>-Terminal Surrogate in Amino Acid and Peptide Analogues
  作者：George Varvounis、Paul Cordopatis、Evangelos E. Bissyris、Dimitris Belekos、Vassiliki Magafa、Petros G. Tsoungas

  DOI：10.1055/s-2005-918426

  日期：——

  (ATPC) is an unnatural amino acid with promise in applications as a building block for the synthesis of peptidomimetics. ATPC was obtained from both 3a and 3b thienopyrimidines by hydrolysis and hydrogenolysis, respectively. The synthesis of eleven ATPC-amino acids and two ATPC-peptides is described. ATPC is incorporated as N-terminal moiety in solution or solid-phase peptide synthesis using Boc or

  2-Amino-4-pyrrolidinothieno[2,3-d]pyrimidine-6-carboxy acid (4) (ATPC) 是一种非天然氨基酸，有望作为合成肽模拟物的构件。ATPC 分别通过水解和氢解从 3a 和 3b 噻吩并嘧啶中获得。描述了十一种ATPC-氨基酸和两种ATPC-肽的合成。使用 Boc 或 Fmoc 方法将 ATPC 作为 N 端部分引入溶液或固相肽合成中，而无需保护 ATPC 氨基。
• Peptidomimetic organocatalysts: efficient Michael addition of ketones onto nitroolefins with very low catalyst loading
  作者：Srivari Chandrasekhar、Chintakunta Praveen Kumar、Togapur Pavan Kumar、Kothapalli Haribabu、Bharatam Jagadeesh、Jerripothula K. Lakshmi、Prathama S. Mainkar

  DOI：10.1039/c4ra04165h

  日期：——

  The syntheses of two novel peptidomimetic triazole-based organocatalysts that work for the asymmetric conjugate addition of cyclohexanone to nitroolefins are described. The catalysts worked with very low loading (0.5 mol%) in the absence of any additives to provide high diastereo- and enantio-selectivities.

  描述了两种新型的拟肽三唑类有机催化剂的合成，这些催化剂可用于将环己酮不对称地加成到硝基烯烃中。在不存在任何添加剂的情况下，催化剂以非常低的负载量（0.5mol％）工作，以提供高的非对映选择性和对映选择性。
• Structure-activity relationships of C-terminal tri- and tetrapeptide fragments that inhibit gastrin activity
  作者：Jean Martinez、Jean Pierre Bali、Richard Magous、Janine Laur、Marie Francoise Lignon、Christian Briet、Dino Nisato、Bertrand Castro

  DOI：10.1021/jm00381a002

  日期：1985.3

  A series of tri- and tetrapeptide derivatives, analogues of the gastrin C-terminal region with no phenylalanine residue, were synthesized. These peptides were tested for their ability to inhibit gastrin-stimulated acid secretion in vivo as well as binding of [125I]-(Nle11)-HG-13 to gastric mucosal cell receptors in vitro. Most of the peptides tested exhibited gastrin antagonist activity in vivo and in vitro. Most active derivatives were 20-30 times more potent than the well-known gastrin antagonist derivatives proglumide and benzotript and had 20-200 times more binding affinity. The smallest fragment exhibiting antagonist activity was the tripeptide Boc-L-tryptophyl-L-methionyl-L-aspartic acid amide.
• Synthesis of structural analogs of the 13–16 fragment of gastrin, and their effects on gastric secretion
  作者：Yu. M. Taskaeva、G. A. Korshunova、L. S. Vasilevskaya、Yu. P. Shvachkin

  DOI：10.1007/bf00766860

  日期：1990.2