Z-Gly-Phe-Leu-NH2 | 69193-15-3

• 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: Z-Gly-Phe-Leu-NH2
• 英文别名: Z-Gly-L-Phe-L-Leu-NH2；N-[(Benzyloxy)carbonyl]glycyl-L-phenylalanyl-L-leucinamide；benzyl N-[2-[[(2S)-1-[[(2S)-1-amino-4-methyl-1-oxopentan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-2-oxoethyl]carbamate
• CAS: 69193-15-3
• 化学式: C₂₅H₃₂N₄O₅
• 分子量: 468.553
• InChiKey: IAXNXNLMTMBSTO-SFTDATJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  34
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  140
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Z-Gly-Phe-Leu-NH2 在 papain thio-2-hydroxyethylene 作用下， 以 甲醇 、 水 为溶剂， 反应 6.0h， 生成 Z-Tyr-Gly-Gly-Phe-Leu-NH₂
  参考文献：
  名称：

  木瓜蛋白酶催化的肽合成：酰胺酶活性的控制和异常氨基酸的引入

  摘要：

  已经开发了木瓜蛋白酶催化的合成含有D-氨基酸的肽和可控制该酶的酰胺酶活性的衍生物的方法。

  DOI：

  10.1039/c39870000533
• 作为产物：
  描述：

  亮氨酰胺 在 papain thio-2-hydroxyethylene 作用下， 以 甲醇 、 水 为溶剂， 反应 6.0h， 生成 Z-Gly-Phe-Leu-NH2
  参考文献：
  名称：

  木瓜蛋白酶催化的肽合成：酰胺酶活性的控制和异常氨基酸的引入

  摘要：

  已经开发了木瓜蛋白酶催化的合成含有D-氨基酸的肽和可控制该酶的酰胺酶活性的衍生物的方法。

  DOI：

  10.1039/c39870000533

文献信息

• α-Chymotrypsin-catalysed segment condensations via the kinetically controlled approach using carbamoylmethyl esters as acyl donors in organic mediaElectronic supplementary information (ESI) available: elemental analyses and HPLC separation data. See http://www.rsc.org/suppdata/p1/b1/b108738j/
  作者：Toshifumi Miyazawa、Eiichi Ensatsu、Makoto Hiramatsu、Ryoji Yanagihara、Takashi Yamada

  DOI：10.1039/b108738j

  日期：2002.1.23

  The superiority of the carbamoylmethyl ester as an acyl donor for the α-chymotrypsin-catalysed segment condensations via the kinetically controlled approach is demonstrated in several model systems carried out in organic media with low water content. Furthermore, this approach is successfully applied to the construction of the Leu-enkephalin sequence via a 4 + 1 segment coupling.

  在有机介质中低水含量的几个模型体系中，证明了羰甲基酯作为乙酰供体在通过动力学控制方法进行的α-胰凝乳蛋白酶催化的片段缩合反应中的优越性。此外，这种方法成功地应用于通过4+1片段偶联构建亮氨酸脑啡肽序列。
• Kinetically Controlled Peptide Synthesis Mediated by Papain Using the Carbamoylmethyl Ester as an Acyl Donor
  作者：Toshifumi Miyazawa、Takao Horimoto、Kayoko Tanaka

  DOI：10.1007/s10989-014-9393-0

  日期：2014.9

  carbamoylmethyl (Cam) esters as acyl donors in the presence of a cysteine protease, papain, immobilized on Celite. Several segment condensations were also achieved generally in high yields without danger of racemization and formation of the secondary-hydrolysis product. Moreover, partial sequences of some bioactive peptides were prepared through segment condensations, and aimed-at peptides were obtained generally

  在固定于硅藻土的半胱氨酸蛋白酶木瓜蛋白酶存在下，通常以高收率合成一系列二肽，其中氨基甲酰基甲基（Cam）酯为酰基供体。通常也以高收率获得数个段的缩合，而没有消旋化和形成二次水解产物的危险。此外，一些生物活性肽的部分序列是通过片段缩合制备的，并且通常以高收率获得了针对性的肽，而没有羧基组分的C-末端残基的外消旋化。因此，在半胱氨酸介导的偶联中再次确定了Cam酯在动力学控制的肽合成中的优越性。 如先前报道的被丝氨酸蛋白酶催化的那些。
• Superiority of the Carbamoylmethyl Ester as an Acyl Donor for the Protease-catalyzed Kinetically Controlled Peptide Synthesis in Organic Media: Application to Segment Condensations
  作者：Toshifumi Miyazawa、Eiichi Ensatsu、Kayoko Tanaka、Ryoji Yanagihara、Takashi Yamada

  DOI：10.1246/cl.1999.1013

  日期：1999.10

  The superiority of the carbamoylmethyl ester as an acyl donor for the α-chymotrypsin-catalyzed kinetically controlled peptide synthesis was demonstrated in several segment condensations carried out in organic media with low water content. Then this approach was successfully applied to the construction of the Leuenkephalin sequence via the 4 + 1 segment condensation.

  氨基甲酰甲酯作为 α-胰凝乳蛋白酶催化的动力学控制肽合成的酰基供体的优越性在低水含量有机介质中进行的几个片段缩合中得到证明。然后，该方法通过 4+1 段缩合成功应用于 Leuenkephalin 序列的构建。
• Continuous synthesis of a tripeptide by successive condensation and transesterification catalyzed by two immobilized proteinases in organic solvent.
  作者：Yukitaka KIMURA、Tomoko YOSHIDA、Koji MURAYA、Kazuhiro NAKANISHI、Ryuichi MATSUNO

  DOI：10.1271/bbb1961.54.1433

  日期：——

  The tripeptide Z-GlyPheLeuNH2 was continuously synthesized in a high yield from three amino acid derivatives, Z-Gly, PheOMe, and LeuNH2, by immobilized thermolysin (IMT) and immobilized a-chymotrypsin (IMC) in an organic solvent, ethyl acetate. The optimal conditions for the synthesis of Z-GlyPheOMe were established theoretically. The yield of Z-GIyPheOMe with IMT in ethyl acetate saturated with buffer was more than 88% after continuous synthesis for 116hr. The optimal conditions for the synthesis of Z-GlyPheLeuNH2 from Z-GlyPheOMe and LeuNH2 by IMC through transesterification was established in batch reaction experiments. When the concentration of water in the reaction solution was 17-20 μl/ml, the activity of IMC was highest. The equilibrium between the water concentration in the reaction solution and that in the resin used for enzyme immobilization depended on the resin and was not affected by the presence of the enzyme immobilized. Z-GlyPheLeuNH2 was synthesized from Z-GlyPheOMe and LeuNH2 with a yield of 100 %, by continuous reaction for 160 hr. The reactor for synthesis of this tripeptide was efficient and stable because of the use of transesterification and the choice of an appropriate organic solvent. The series plug-flow reactor was successfully operated for 220 hr with a yield of more than 80 %. The residual activity of IMT was 94%, and that of IMC was 100%.

  固定化热溶解酶（IMT）和固定化a-糜蛋白酶（IMC）在有机溶剂乙酸乙酯中连续高产合成了Z-Gly、PheOMe和LeuNH2三种氨基酸衍生物的三肽Z-GlyPheLeuNH2。从理论上确定了合成 Z-GlyPheOMe 的最佳条件。在缓冲液饱和的乙酸乙酯中与 IMT 连续合成 116 小时后，Z-GIyPheOMe 的产率超过 88%。 批量反应实验确定了 IMC 通过酯交换反应从 Z-GlyPheOMe 和 LeuNH2 合成 Z-GlyPheLeuNH2 的最佳条件。当反应溶液中水的浓度为 17-20 μl/ml 时，IMC 的活性最高。反应溶液中的水浓度与用于固定酶的树脂中的水浓度之间的平衡取决于树脂，而不受固定酶存在的影响。通过 160 小时的连续反应，从 Z-GlyPheOMe 和 LeuNH2 合成了 Z-GlyPheLeuNH2，产率为 100%。 由于使用了酯交换反应并选择了适当的有机溶剂，合成这种三肽的反应器既高效又稳定。串联塞流反应器成功运行了 220 小时，收率超过 80%。IMT 的残余活性为 94%，IMC 的残余活性为 100%。
• Peptidsynthesen mit immobilisierten Enzymen. I. Immobilisiertes ?-Chymotrypsin
  作者：Andreas K�nnecke、Ralf Bullerjahn、Hans-Dieter Jakubke

  DOI：10.1007/bf00901826

  日期：1981.4