N^α-benzyloxycarbonylphenylalanylglycylglycine ethyl ester | 4526-84-5

• 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: N^α-benzyloxycarbonylphenylalanylglycylglycine ethyl ester
• 英文别名: Z-Phe-Gly-Gly-OEt；Z-PheGlyGlyOEt；N-benzyloxycarbonyl-L-phenylalanyl=>glycyl=>glycine ethyl ester；N-Benzyloxycarbonyl-L-phenylalanyl=>glycyl=>glycin-aethylester；ethyl 2-[[2-[[(2S)-3-phenyl-2-(phenylmethoxycarbonylamino)propanoyl]amino]acetyl]amino]acetate
• CAS: 4526-84-5
• 化学式: C₂₃H₂₇N₃O₆
• 分子量: 441.484
• InChiKey: INIZGPHDPAQXJM-IBGZPJMESA-N

物化性质

• 熔点：
  196-197 °C
• 沸点：
  723.3±60.0 °C(Predicted)
• 密度：
  1.227±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  32
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  123
• 氢给体数：
  3
• 氢受体数：
  6

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  N^α-benzyloxycarbonylphenylalanylglycylglycine ethyl ester 在 氢溴酸 、 三乙胺 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 1.5h， 生成 N^α-furylacryloylphenylalanylglycylglycine ethyl ester
  参考文献：
  名称：

  Pozdnev, V. F., Journal of general chemistry of the USSR, 1986, vol. 56, p. 613 - 617

  摘要：

  DOI：
• 作为产物：
  描述：

  Z-L-苯丙氨酸-8-喹啉酯 、 H-gly-gly-oet.盐酸盐 在 1-羟基苯并三唑 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以87%的产率得到N^α-benzyloxycarbonylphenylalanylglycylglycine ethyl ester
  参考文献：
  名称：

  Pozdnev, V. F., Journal of general chemistry of the USSR, 1986, vol. 56, p. 613 - 617

  摘要：

  DOI：

文献信息

• Full enzymatic synthesis of a precursor of bioactive pentapeptide OGP(10-14) in organic solvents
  作者：Ping Liu、Gui-ling Tian、Kin-Sing Lee、Man-Sau Wong、Yun-hua Ye

  DOI：10.1016/s0040-4039(02)00278-2

  日期：2002.3

  Full enzymatic synthesis of a fragment of osteogenic growth peptide (OGP), a precursor of bioactive pentapeptide OGP(10-14) (Z-TyrGlyPheGlyGlyOEt), was accomplished by papain, α-chymotrypsin, and thermolysin via 2+3 or 3+2 synthetic routes in organic solvents for the first time. The factors influencing the enzymatic synthesis of fragments of OGP(10-14) were systematically studied.

  通过木瓜蛋白酶，α-胰凝乳蛋白酶和嗜热菌蛋白酶通过2 + 3或3 + 2完全酶促合成成骨生长肽（OGP）片段，该片段是生物活性五肽OGP（10-14）的前体（Z-TyrGlyPheGlyGlyOEt）。首次在有机溶剂中合成路线。系统地研究了影响OGP（10-14）片段酶促合成的因素。
• Synthesis of a Precursor of Bioactive Pentapeptide OGP-(10-14) and the Fragment of Enkephalin Catalyzed by MCM-22 Immobilized or Free Proteases in Organic Solvents
  作者：Ping Liu、Yun-hua Ye、Gui-ling Tian、Kin-Sing Lee、Man-Sau Wong、Wai-hung Lo

  DOI：10.1055/s-2002-25762

  日期：——

  Full enzymatic synthesis of a precursor of osteogenic growth peptide fragment (10-14), Z-Tyr-Gly-Phe-Gly-Gly--OEt, was accomplished using immobilized proteases on molecular sieve MCM-22 by adsorption as catalyst via 3+2 synthetic route for the first time. The reuse time of immobilized enzyme was dependent on concrete reaction system. Compared with free enzyme, the reaction rate catalyzed by immobilized

  成骨生长肽片段 (10-14) 的前体 Z-Tyr-Gly-Phe-Gly-Gly--OEt 的全酶合成是使用固定化蛋白酶在分子筛 MCM-22 上通过吸附作为催化剂通过 3+ 2合成路线首次。固定化酶的重复使用时间取决于具体的反应体系。与游离酶相比，大多数情况下固定化酶催化的反应速率明显提高，合成产率也有所提高。含水量和Et 3 N的添加量对固定化酶合成OGP-(I 0-14)和脑啡肽等生物活性肽片段的影响与游离酶不同。
• Carbohydrate Protease Conjugates: Stabilized Proteases for Peptide Synthesis
  作者：Charles A. Wartchow、Peng Wang、Mark D. Bednarski、Matthew R. Callstrom

  DOI：10.1021/jo00112a049

  日期：1995.4

  The synthesis of oligopeptides using stable carbohydrate protease conjugates (CPCs) was examined in acetonitrile solvent systems. CPC[alpha-chymotrypsin] was used for the preparation of peptides containing histidine, phenylalanine, tyrosine, and tryptophan in the P-1 position in 60-93% yield. The CPC[alpha-chymotrypsin]-catalyzed synthesis of octamer Z-Gly-Gly-Phe-Gly-Gly-Phe-Gly-Gly-OEt from Z-Gly-Gly-Phe-Gly-Gly-Phe-OMe was achieved in 71% yield demonstrating that synthesis was the dominant kinetic process relative to amide hydrolysis. CPC[papain] was used to synthesize peptides containing both hydrophilic and hydrophobic amino acids. The Pt specificity of papain for aromatic residues was utilized for the 2 + 3 coupling of Z-Tyr-Gly-OMe to H2N-Gly-Phe-Leu-OH to generate the leucine enkephalin derivative in 79% yield. Although papain is nonspecific for the hydrolysis of N-benzyloxycarbonyl amino acid methyl esters in aqueous solution, the rates of synthesis for these derivitives with nucleophile leucine tert-butyl ester differed by nearly 2 orders of magnitude. CPC[thermolysin] was used to prepare the aspartame precursor Z-Asp-Phe-OMe in 90% yield. The increased stability of CPCs prepared from periodate-modified poly(2-methacrylamido-2-deoxy-D-glucose), poly(2-methacrylamido-2-deoxy-D-galactcose) and poly(5-methacrylamido-5-deoxy-D-ribose), carbohydrate materials designed to increase the aldehyde concentration in aqueous solution, suggests that the stability of CPCs is directly related to the aldehyde concentration of the carbohydrate material. Periodate oxidation of poly(2-methacrylamido-2-deoxy-D-glucose) followed by covalent attachment to a-chymotrypsin gave a CPC with catalytic activity in potassium phosphate buffer at 90 degrees C for 2 h.
• Panneman et al., Recueil des Travaux Chimiques des Pays-Bas, 1959, vol. 78, p. 487,499
  作者：Panneman et al.

  DOI：——

  日期：——
• Pozdnev, V. F., Journal of general chemistry of the USSR, 1986, vol. 56, p. 613 - 617
  作者：Pozdnev, V. F.

  DOI：——

  日期：——