Z-L-Phe-L-Pro-OtBu | 2899-09-4

• 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-L-Phe-L-Pro-OtBu
• 英文别名: benzyloxycarbonyl-L-phenylalanyl-L-proline tert-butyl ester；N-Benzyloxycarbonyl-L-phenylalanyl-L-proline t-butyl ester；N-carbobenzoxy-L-phenylalanyl-L-proline tert-butyl ester；Cbz-L-Phe-L-Pro-OtBu；tert-butyl (2S)-1-[(2S)-3-phenyl-2-(phenylmethoxycarbonylamino)propanoyl]pyrrolidine-2-carboxylate
• CAS: 2899-09-4
• 化学式: C₂₆H₃₂N₂O₅
• 分子量: 452.55
• InChiKey: QFNUHJFWMLXDHY-VXKWHMMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  84.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Z-L-Phe-L-Pro-OtBu 在 palladium on activated charcoal 氢气 、 溶剂黄146 作用下， 反应 10.0h， 生成 L-phenylalanyl-L-proline tert-butyl ester
  参考文献：
  名称：

  衣原霉素-异羟肟酸类似物作为组蛋白脱乙酰基酶抑制剂。

  摘要：

  根据衣原霉素和曲古抑菌素A的结构和HDAC抑制活性，设计并合成了衣原霉素-异羟肟酸类似物作为组蛋白脱乙酰基酶（HDAC）抑制剂。衣原霉素是环状四肽，在侧链中含有环氧酮部分，使其成为不可逆抑制剂。 HDAC。我们用异羟肟酸代替了衣原体的环氧酮部分，以设计有效且可逆的HDAC抑制剂。另外，对于一系列衣藻多菌素类似物系列，引入了许多氨基-环烷羧酸（Acc）而不是简单的氨基-异丁酸（Aib）。测试了所合成的化合物的HDAC抑制活性，结果表明其中许多是HDAC的有效抑制剂。用芳香族氨基酸代替衣原体的Aib残基增强了体内和体外的抑制活性。我们已经对衣原霉素-异羟肟酸类似物进行了圆二色性和分子模拟研究，并将其与衣原霉素的溶液结构进行了比较。

  DOI：

  10.1016/j.bmc.2004.08.041
• 作为产物：
  描述：

  Z-L-Phe-CAM 、 L-脯氨酸叔丁酯 在 cross-linked enzyme aggregate of Alcalase 作用下， 反应 16.0h， 以92%的产率得到Z-L-Phe-L-Pro-OtBu
  参考文献：
  名称：

  Enzymatic synthesis of activated esters and their subsequent use in enzyme-based peptide synthesis

  摘要：

  Chemoenzymatic peptide synthesis is potentially the most cost-efficient technology for the synthesis of short and medium-sized peptides. However, there are still some limitations when challenging peptides, e.g. containing sterically demanding acyl donors, non-proteinogenic amino acids or proline residues, are to be synthesized. To remedy these limitations, special ester moieties have been used that are specifically recognized by the enzyme, e.g. guanidinophenyl, carboxamidomethyl (Cam) or trifluoroethyl (Tfe) esters, which, unfortunately, are notoriously difficult to synthesize chemically. Herein, we demonstrate that Cam and Tfe esters are very useful for Alcalase-CLEA mediated peptide synthesis using sterically demanding and non-proteinogenic acyl donors as well as poor nucleophiles, and combinations thereof. Furthermore, these esters can be efficiently synthesized by using the lipase Cal-B or Alcalase-CLEA. Finally, it is shown that the ester synthesis by Cal-B and subsequent peptide synthesis by Alcalase-CLEA can be performed simultaneously using a two-enzyme-one-pot approach with glycolamide or 2,2,2-trifluoroethanol as additive. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2011.03.012

文献信息

• Peptide aldehydes as antithrombotic agents
  申请人：Bristol-Myers Squibb Company

  公开号：US05380713A1

  公开（公告）日：1995-01-10

  This invention relates to novel arginine aldehydes, their salts and hydrates, which compounds selectively exhibit serine proteases inhibitory activity, are highly stable in aqueous solutions, and are useful for anti-trypsin and anti-thrombin activity.

  该发明涉及新型精氨酸醛类化合物及其盐和水合物，这些化合物具有选择性地表现出丝氨酸蛋白酶抑制活性，在水溶液中具有高稳定性，并且对抗胰蛋白酶和抗凝血酶活性具有用处。
• Process for preparing oxazolo\x9b3,2-a!pyrrolo\x9b2,1-c!pyrazine derivatives \n'
  申请人：Sandoz Ltd.

  公开号：US04145549A1

  公开（公告）日：1979-03-20

  The present invention provides a novel cyclization process useful for the production of the peptide moiety of an ergotalkaloid.

  本发明提供了一种新的环化过程，用于生产麦角生物碱的肽基团。
• Proline derivatives
  申请人：ICI AMERICAS INC.

  公开号：EP0124317A2

  公开（公告）日：1984-11-07

  Proline derivatives of the formulae: wherein R1 through R11 have defined values, and acid- and base-addition salts thereof, and equilibrium addition compounds of the aldehyde group thereof; processes for their preparation; pharmaceutical compositions; and intermediates for preparing said proline derivatives. The proline derivatives are human leukocyte elastase inhibitors which are useful, for example, in treating pulmonary emphysema.

  式中的脯氨酸衍生物： 式中 R1 至 R11 具有定义值的脯氨酸衍生物、其酸加成盐和碱加成盐、其醛基的平衡加成化合物；其制备工艺；药物组合物；以及制备上述脯氨酸衍生物的中间体。脯氨酸衍生物是人类白细胞弹性蛋白酶抑制剂，可用于治疗肺气肿等疾病。
• ——
  作者：

  DOI：——

  日期：——
• US4145549A
  申请人：——

  公开号：US4145549A

  公开（公告）日：1979-03-20