2,4,5-trichlorophenyl ester N-(benzyloxycarbonyl)-L-alanine | 7536-54-1

• 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: 2,4,5-trichlorophenyl ester N-(benzyloxycarbonyl)-L-alanine
• 英文别名: N-carbobenzoxy-L-alanine 2,4,5-trichlorophenyl ester；Z-Ala-OTcp；Z-Ala-OCp；Z-Ala-OTCP；Z-Ala-TCP；(2,4,5-trichlorophenyl) (2S)-2-(phenylmethoxycarbonylamino)propanoate
• CAS: 7536-54-1
• 化学式: C₁₇H₁₄Cl₃NO₄
• 分子量: 402.661
• InChiKey: ZNVWBEIILSUHOR-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,4,5-trichlorophenyl ester N-(benzyloxycarbonyl)-L-alanine 在 氢溴酸 作用下， 以 溶剂黄146 为溶剂， 生成 (2,4,5-trichlorophenyl) (2S)-2-aminopropanoate
  参考文献：
  名称：

  Synthesis of 2,4,5-trichlorophenyl esters of tert-butyloxycarbonyl tripeptides containing the lysine residue

  摘要：

  DOI：

  10.1007/bf00854935
• 作为产物：
  描述：

  苄氧羰基-L-丙氨酸 、 2,4,5-三氯苯酚 在 N,N'-二环己基碳二亚胺 作用下， 生成 2,4,5-trichlorophenyl ester N-(benzyloxycarbonyl)-L-alanine
  参考文献：
  名称：

  氨基酸，氨基酸，N-锗，α-氨基-苯基酯，insbesondere 2,4,5-三氯苯基酯

  摘要：

  N-保护的α-氨基酸的许多取代苯基酯的氨解率的比较表明，2,4,5-三氯苯基酯是合成肽的有希望的新活性衍生物。

  DOI：

  10.1002/hlca.19630460516

文献信息

• Synthèse d'analogues structuraux de l'élédoïsine. 1^repartie: Préparation des produits intermédiaires
  作者：Ed. Sandrin、R. A. Boissonnas

  DOI：10.1002/hlca.19630460518

  日期：——

  The preparation of new dipeptides and tripeptides, which are useful intermediates in the synthesis of Eledoisin analogues, is described.

  描述了新的二肽和三肽的制备，它们是Eledoisin类似物合成中的有用中间体。
• Polypeptides. Part VIII. Variations of the aspartyl position in the C-terminal tetrapeptide amide sequence of the gastrins
  作者：H. Gregory、J. S. Morley、J. M. Smith、M. J. Smithers

  DOI：10.1039/j39680000715

  日期：——

  The synthesis is described of analogues of L-tryptophyl-L-methionyl-L-aspartyl-L-phenylalanine amide (the C-terminal sequence of the gastrins), and its N-benzyloxycarbonyl or N-t-butoxycarbonyl derivatives, wherein the aspartyl residue has undergone replacement by alanyl, β-aspartyl, asparaginyl, cysteinyl, glutamyl, glycyl, lysyl, norvalyl, ornithyl, seryl, threonyl, and other amino-acyl residues

  描述了L-色氨酸-L-甲硫酰基-L-天冬氨酰-L-苯丙氨酸酰胺（胃泌素的C-末端序列）及其N-苄氧羰基或N-叔丁氧羰基衍生物的类似物的合成，其中天冬氨酰残基已被丙氨酰基，β-天冬氨酰，天冬酰胺基，半胱氨酰基，谷氨酰基，甘氨酰基，赖氨酰基，降冰片酰基，鸟氨酸残基，丝氨酰基，苏氨酰基和其他氨基酰基残基取代。
• Pepstatin analogs as novel renin inhibitors
  作者：Remy Guegan、Joseph Diaz、Catherine Cazaubon、Michel Beaumont、Claude Carlet、Jacques Clement、Henri Demarne、Michel Mellet、Jean Paul Richaud

  DOI：10.1021/jm00157a006

  日期：1986.7

  Pepstatin analogues corresponding to the general formula A-X-Y-Sta-Ala-Sta-R were synthesized in solution phase. Various changes in the nature of the A, X, and Y groups were made to improve the inhibitory potency against human plasma renin activity. The results were interpreted by use of the active-site model based on the sequence of human angiotensinogen. The tert-butyloxycarbonyl group and the isovaleryl

  在溶液相中合成对应于通式AXY-Sta-Ala-Sta-R的胃抑素类似物。进行了A，X和Y基团性质的各种变化以提高对人血浆肾素活性的抑制能力。通过使用基于人类血管紧张素原序列的活性位点模型来解释结果。发现叔丁氧羰基和异戊酰基是最有效的酰基（A）。在Y位置具有Phe残基代替Val1（X）和His或具有脂肪族侧链的氨基酸（如正亮氨酸或正缬氨酸）的类似物显示出对人血浆肾素活性的最高抑制作用，IC50值约为10（-8） M. C-末端他汀类化合物的羧基的酯化或酰胺化不会改变抑制能力。
• Peptides. Part XXVII. Synthesis of five heptadecapeptides related to human gastrin
  作者：K. L. Agarwal、G. W. Kenner、R. C. Sheppard

  DOI：10.1039/j39680001384

  日期：——

  The synthesis of five analogues of gastrin with various biologically essential features of the C-terminal tetrapeptide amide sequence modified is described. No compounds with inhibitory effects upon the activity of the natural hormone were obtained.

  描述了具有修饰的C末端四肽酰胺序列的各种生物学基本特征的胃泌素的五个类似物的合成。没有获得对天然激素活性具有抑制作用的化合物。
• Angiotensin converting enzyme inhibitors. (Mercaptoaroyl)amino acids
  作者：Paul R. Menard、John T. Suh、Howard Jones、Bernard Loev、Edward S. Neiss、Joyce Wilde、Alfred Schwab、William S. Mann

  DOI：10.1021/jm00381a012

  日期：1985.3

  A series of (mercaptoaroyl)amino acids and related compounds was synthesized and tested for ability to inhibit angiotensin converting enzyme (ACE). The most active compound was N-(3-chloro-2-mercaptobenzoyl)-N-cyclopentylglycine, having an in vitro I50 = 0.28 microM. Substitution of the aromatic 3-position by small polar groups enhanced ACE inhibitory activity, whereas bulky groups diminished it. Alteration of the beta relationship between the mercaptan and amide carbonyl or masking of the thiol by acylation reduced activity. Replacement of the thiol by nitro, hydroxy, or carboxy gave compounds lacking ACE inhibitory activity.