N-cbz-L-Phe-L-Phe-L-Leu-NH2 | 126028-19-1

• 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: N-cbz-L-Phe-L-Phe-L-Leu-NH2
• 英文别名: Z-L-Phe-L-Phe-L-Leu-NH2；Z-PhePheLeuNH2；Cbz-Phe-Phe-Leu-NH2；benzyl N-[(2S)-1-[[(2S)-1-[[(2S)-1-amino-4-methyl-1-oxopentan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]carbamate
• CAS: 126028-19-1
• 化学式: C₃₂H₃₈N₄O₅
• 分子量: 558.678
• InChiKey: BVGSHCOCFFRAGE-KCHLEUMXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  41
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  140
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-苄氧羰基-L-苯丙氨酰基-L-苯丙氨酸 在 α-chymotrypsin immobilised on Celite 、 caesium carbonate 、 三乙胺 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 1.0h， 生成 N-cbz-L-Phe-L-Phe-L-Leu-NH2
  参考文献：
  名称：

  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/

  摘要：

  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。

  DOI：

  10.1039/b108738j

文献信息

• Enzymatic peptide syntheses in organic solvent mediated by modified α-chymotrypsin
  作者：Marie-Thérèse Babonneau、Robert Jacquier、René Lazaro、Philippe Viallefont

  DOI：10.1016/s0040-4039(00)99125-1

  日期：1989.1

  Peptide couplings have been catalyzed in organic medium containing a slight amount of water (<0,5%) by PEG modified α-Chymotrypsin.

  肽偶联已通过PEG修饰的α-胰凝乳蛋白酶在含有少量水（<0.5％）的有机介质中催化。
• 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。
• Cross-Linked Crystals of Subtilisin:  Versatile Catalyst for Organic Synthesis
  作者：Yi-Fong Wang、Kirill Yakovlevsky、Bailing Zhang、Alexey L. Margolin

  DOI：10.1021/jo9618334

  日期：1997.5.1

  Cross-linked enzyme crystals (CLECs) of subtilisin exhibit excellent activity in aqueous and various organic solvents. This catalyst is more stable than the native enzyme in both aqueous and mixed aqueous/organic solutions. Subtilisin-CLEC was shown to be a versatile catalyst. It was used for the syntheses of peptides and peptidomimetics, mild hydrolysis of amino acid and peptide amides, enantio- and regioselective reactions, and transesterifications.
• BABONNEAU, MARIE-THERESE;JACQUIER, ROBERT;LAZARO, RENE;VIALLEFONT, PHILIP+, TETRAHEDRON LETT., 30,(1989) N1, C. 2787-2790
  作者：BABONNEAU, MARIE-THERESE、JACQUIER, ROBERT、LAZARO, RENE、VIALLEFONT, PHILIP+

  DOI：——

  日期：——