benzyloxycarbonyl-(S)-phenylalanyl-(S)-histidine methyl ester | 16689-13-7

• 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: benzyloxycarbonyl-(S)-phenylalanyl-(S)-histidine methyl ester
• 英文别名: Benzyloxycarbonyl-Phe-His-OMe；Z-Phe-His-OMe；N^α-(N-benzyloxycarbonyl-phenylalanyl)-histidine methyl ester；N-benzyloxycarbonyl-L-phenylalanyl-L-histidine methyl ester；Benzyloxycarbonylphenylalanylhistidin-methylester；methyl (2S)-3-(1H-imidazol-5-yl)-2-[[(2S)-3-phenyl-2-(phenylmethoxycarbonylamino)propanoyl]amino]propanoate
• CAS: 16689-13-7
• 化学式: C₂₄H₂₆N₄O₅
• 分子量: 450.494
• InChiKey: AAAHCXVACIMZHZ-SFTDATJTSA-N

物化性质

• 熔点：
  119 °C(Solv: ethyl acetate (141-78-6); ligroine (8032-32-4))
• 沸点：
  763.4±60.0 °C(Predicted)
• 密度：
  1.275±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  33
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  122
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  benzyloxycarbonyl-(S)-phenylalanyl-(S)-histidine methyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 乙醇 为溶剂， 生成 (3S,6S)-3-((1H-Imidazol-5-yl)methyl)-6-benzylpiperazine-2,5-dione
  参考文献：
  名称：

  Arena, Giuseppe; Impellizzeri, Giuseppe; Maccarrone, Giuseppe, Journal of the Chemical Society. Perkin transactions II, 1992, # 3, p. 371 - 376

  摘要：

  DOI：
• 作为产物：
  描述：

  N-苄氧羰基-L-苯丙氨酸 在 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 氯仿 为溶剂， 生成 benzyloxycarbonyl-(S)-phenylalanyl-(S)-histidine methyl ester
  参考文献：
  名称：

  Arena, Giuseppe; Impellizzeri, Giuseppe; Maccarrone, Giuseppe, Journal of the Chemical Society. Perkin transactions II, 1992, # 3, p. 371 - 376

  摘要：

  DOI：

文献信息

• Imidazole-containing peptide and preparation thereof
  申请人：TANABE SEIYAKU CO., LTD.

  公开号：EP0372818A2

  公开（公告）日：1990-06-13

  Imidazole-containing peptide of the formula: wherein R1 is a branched alkyl group, a branched alkyloxy group or an aryl-substituted lower alkyloxy group, R2 and R4 are the same or different and each is hydrogen atom or a lower alkyl group, R3 and RS are a phenyl-substituted lower alkyl group, R6 is hydrogen atom or a lower alkoxycarbonyl group, R7 is hydrogen atom or a nitrogen-containing heterocyclic group-substituted lower alkylthio group, X1 and X2 are the same or different and each is - N -, A is a lower alkylene group which may be substituted with a substituent selected from the group consisting of a lower alkoxy group, hydroxymethyl group and a group of the formula: and R8 and R9 are the same or different and each is hydrogen atom or a lower group, or a pharmaceutically acceptable salt thereof, which is useful as an immunomodulator and as an agent for the treatment and/or prophylaxis of autoimmune diseases such as rheumatoid arthritis, mulripule sclerosis, systemic lupus erthematodes, glomerulonephris,rhumatic fever or type I diabetes and atopic allergy, a processes for the preparation thereof, and a pharmaceutical composition containing said compound as an active ingredient.

  式中的含咪唑肽： 其中 R1 为支链烷基、支链烷氧基或芳基取代的低级烷氧基，R2 和 R4 相同或不同，且各自为氢原子或低级烷基，R3 和 RS 为苯基取代的低级烷基，R6 为氢原子或低级烷氧基羰基，R7 为氢原子或含氮杂环基取代的低级烷硫基，X1 和 X2 相同或不同，且各自为 - N -，A 是低级亚烷基，可被选自低级烷氧基、羟甲基和式中基团的取代基取代： 和 R8 和 R9 相同或不同，且各自为氢原子或低级基团，或其药学上可接受的盐，可用作免疫调节剂和治疗和/或预防自身免疫性疾病如类风湿性关节炎、毛滴虫硬化症、系统性红斑狼疮、肾小球肾炎、风湿热或 I 型糖尿病和特应性过敏的制剂，其制备工艺，以及含有所述化合物作为活性成分的药物组合物。
• Renin inhibitors. Synthesis of transition-state analog inhibitors containing phosphorus acid derivatives at the scissile bond
  作者：Mark C. Allen、Walter Fuhrer、Brian Tuck、Roy Wade、Jeanette M. Wood

  DOI：10.1021/jm00127a041

  日期：1989.7

  The synthesis of five amino phosphorus derivatives, 1a-e, is described. The derivatives were incorporated into a series (18) of analogues of the 5-14 portion of angiotensinogen, in most cases at the scissile Leu-Val bond. The resultant compounds were tested in vitro for their ability to inhibit human plasma renin. Replacement of the scissile bond with the phosphinic analogue of Leu10-Val11 (1b) gave the most potent inhibitors, having IC50 = 7.5 x 10(-8) M for H-Pro-His-Pro-Phe-His-(1b)-Ile-His-Lys-OH and IC50 = 1.0 x 10(-7) M for Z-Arg-Arg-Pro-Phe-His-(1b)-Ile-His-NH2. The shorter phosphonic acid sequence Z-Pro-Phe-His-(1d) retained biological activity with an IC50 = 6.4 x 10(-6) M.
• Appel, Rolf; Glaesel, Ursula; Glaesel, Volker Ingo, Chemische Berichte, 1981, vol. 114, # 4, p. 1542 - 1545
  作者：Appel, Rolf、Glaesel, Ursula、Glaesel, Volker Ingo

  DOI：——

  日期：——
• Mechanism of enantioselective ester cleavage by histidine containing dipeptides at a micellar interface
  作者：Marco C. Cleij、Wiendelt Drenth、Roeland J. M. Nolte

  DOI：10.1021/jo00012a019

  日期：1991.6

  Chiral p-nitrophenyl esters derived from the amino acid phenylalanine are cleaved by histidine-containing dipeptides at a micellar interface. High enantioselectivities (up to k(L)/k(D) = 30.4 at 0-degrees-C) are observed. Both the substrates and the catalysts contain an alternating sequence of hydrophobic and hydrophilic groups. Due to the need for hydration of the hydrophilic groups, the hydrophobic groups cannot dissolve completely into the micellar hydrocarbon phase. The kinetic data suggest that the micellar interface is capable of discriminating between transition states that have different hydrophilic and hydrophobic properties. One of the diastereomeric transition states is characterized by a hydrogen bond between the amide CO group of the ester and an NH group of the histidine-containing dipeptide. Upon formation of this hydrogen bond these polar CO and NH groups lose their hydrophilicity which allows the transfer of the adjacent apolar groups to the micellar hydrocarbon phase. The other diastereomeric transition state cannot form this hydrogen bond and the hydrophobic groups remain hydrated. Consequently, the latter transition state is of higher energy. The kinetic data reveal that it is important to prevent steric hinderance between the reactants in order to allow the unhindered formation of the hydrogen bond.
• Mori, Atsunori; Ikeda, Yoshitaka; Kinoshita, Koichi, Chemistry Letters, 1989, p. 2119 - 2122
  作者：Mori, Atsunori、Ikeda, Yoshitaka、Kinoshita, Koichi、Inoue, Shohei

  DOI：——

  日期：——