Z-Phe-Leu-OtBu | 29842-94-2

• 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-Phe-Leu-OtBu
• 英文别名: Cbz-Phe-Leu-Ot-Bu；tert-butyl (2S)-4-methyl-2-[[(2S)-3-phenyl-2-(phenylmethoxycarbonylamino)propanoyl]amino]pentanoate
• CAS: 29842-94-2
• 化学式: C₂₇H₃₆N₂O₅
• 分子量: 468.593
• InChiKey: BQWCXZAVMXCUTO-GOTSBHOMSA-N

物化性质

• 沸点：
  635.1±55.0 °C(Predicted)
• 密度：
  1.114±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  34
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Z-Phe-Leu-OtBu 在 cross-linked enzyme aggregate of Alcalase 、 水 作用下， 反应 16.0h， 以84%的产率得到N-[N-[(phenylmethoxy)carbonyl]-L-phenylalanyl]-L-leucine
  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
• 作为产物：
  描述：

  N-(苄氧羰基)-L-苯丙氨酸甲酯 在 氢氧化钾 、 phosphate buffer 、 水 、 巯基乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.17h， 生成 Z-Phe-Leu-OtBu
  参考文献：
  名称：

  On the use of carboxamidomethyl esters in the protease-catalyzed peptide synthesis

  摘要：

  DOI：

  10.1007/bf00811332

文献信息

• Naphthoquinones as Covalent Reversible Inhibitors of Cysteine Proteases—Studies on Inhibition Mechanism and Kinetics
  作者：Philipp Klein、Fabian Barthels、Patrick Johe、Annika Wagner、Stefan Tenzer、Ute Distler、Thien Anh Le、Paul Schmid、Volker Engel、Bernd Engels、Ute A. Hellmich、Till Opatz、Tanja Schirmeister

  DOI：10.3390/molecules25092064

  日期：——

  investigation of a class of highly potent protease inhibitors based on 1,4-naphthoquinones with a dipeptidic recognition motif (HN-l-Phe-l-Leu-OR) in the 2-position and an electron-withdrawing group (EWG) in the 3-position is presented. One of the compound representatives, namely the acid with EWG = CN and with R = H proved to be a highly potent rhodesain inhibitor with nanomolar affinity. The respective benzyl

  基于 1,4-萘醌的一类高效蛋白酶抑制剂的简易合成和详细研究，在 2 位具有二肽识别基序 (HN-l-Phe-l-Leu-OR) 和一个吸电子基团(EWG) 在 3 位置呈现。其中一个化合物代表，即 EWG = CN 和 R = H 的酸被证明是一种具有纳摩尔亲和力的高效罗得沙因抑制剂。发现相应的苄酯 (R = Bn) 被目标酶本身水解，产生游离酸。详细的动力学和质谱研究揭示了一种可逆的共价结合模式。进行了具有不同密度泛函 (DFT) 以及基于波函数的方法的理论计算，以阐明作用模式。
• Magnesium/hydrazinium monoformate: a new hydrogenation method for removal of some commonly used protecting groups in peptide synthesis
  作者：D. Channe Gowda

  DOI：10.1016/s0040-4039(01)02113-x

  日期：2002.1

  Removal of some commonly used protecting groups in peptide synthesis by catalytic transfer hydrogenation employing hydrazinium monoformate and magnesium is described. This method is equally competitive with other methods in deblocking most of the commonly used protecting groups in peptide synthesis. tert-Butyl derived and base labile protecting groups were completely stable under these conditions.

  描述了通过使用一甲酸肼盐和镁的催化转移氢化除去肽合成中一些常用的保护基。在解封肽合成中大多数常用的保护基团方面，该方法与其他方法具有同等竞争力。在这些条件下，叔丁基衍生的和不稳定的碱保护基团是完全稳定的。Mg / NH 2 -NH 2 ·HCOOH的使用使它成为钯的快速，低成本替代品，并将后处理减少为简单的萃取操作。
• Fully Enzymatic Peptide Synthesis using C-Terminal tert-Butyl Ester Interconversion
  作者：Timo Nuijens、Claudia Cusan、Theodorus J. G. M. van Dooren、Harold M. Moody、Remco Merkx、John A. W. Kruijtzer、Dirk T. S. Rijkers、Rob M. J. Liskamp、Peter J. L. M. Quaedflieg

  DOI：10.1002/adsc.201000313

  日期：2010.10.4

  Chemoenzymatic peptide synthesis is potentially the most cost-efficient technology for the synthesis of short and medium-sized peptides with some important advantages. For instance, stoichiometric amounts of expensive coupling reagents are not required and racemisation does not occur, thus rendering purification easier compared to chemical peptide synthesis. The economically most attractive synthesis runs in the

  化学酶促肽合成可能是合成短和中等大小肽的最经济有效的技术，具有一些重要的优势。例如，不需要化学计量的昂贵偶联剂，也不会发生外消旋化，因此与化学肽合成相比，纯化更加容易。经济上最具吸引力的合成是在NC末端方向进行的，其中廉价的C末端保护的氨基酸被用作延伸的基础。然而，延长步骤后的C末端脱保护和激活-不会裂解侧链保护基或肽键-仍然是一个挑战。在本文中，我们描述了一种新颖的C丝氨酸内肽酶Alcalase催化末端酯的相互转化。C-末端保护的肽叔丁酯以定量收率被酶促转化为伯烷基酯，并与另一种氨基酸叔丁酯直接用于下一步的酶促延伸步骤。通过C-末端酯互变的这种完全酶促NC延伸策略被用于合成高达五聚体水平的生物活性肽。
• METHOD FOR PRODUCING AMIDE COMPOUND
  申请人：CHUBU UNIVERSITY EDUCATIONAL FOUNDATION

  公开号：US20200131117A1

  公开（公告）日：2020-04-30

  Provided is a novel method for producing amide compounds at high stereochemical selectivities. The method according to the present invention for producing amide compounds is provided with an amidation step for reacting, in the presence of a catalyst comprising a metal compound, an amino compound with an aminoester compound represented by general formula (1) to amidate the ester group in the aminoester compound.

  提供了一种新颖的方法，用于以高立体化学选择性制备酰胺化合物。根据本发明的制备酰胺化合物的方法包括在存在包含金属化合物的催化剂的情况下，进行酰胺化步骤，将氨基化合物与通式（1）所代表的氨基酯化合物反应，以使氨基酯化合物中的酯基酰胺化。
• 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。