Cbz-Lys(Boc)-Ala-OMe | 50466-60-9

• 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: Cbz-Lys(Boc)-Ala-OMe
• 英文别名: Z-Lys(Boc)-Ala-OMe；Z-(ε-Boc)Lys-Ala-OMe；methyl (2S)-2-[[(2S)-6-[(2-methylpropan-2-yl)oxycarbonylamino]-2-(phenylmethoxycarbonylamino)hexanoyl]amino]propanoate
• CAS: 50466-60-9
• 化学式: C₂₃H₃₅N₃O₇
• 分子量: 465.547
• InChiKey: OWTUVDNHYYUXOT-WMZOPIPTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  33
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  132
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Cbz-Lys(Boc)-Ala-OMe 在 甲醇 、 lithium hydroxide monohydrate 、 水 作用下， 反应 2.16h， 以90 mg的产率得到Cbz-Lys(N-Boc)-Ala-OH
  参考文献：
  名称：

  Backbone thioamide directed macrocyclisation: lactam stapling of peptides

  摘要：

  肽硫酰胺中含有天冬氨酸和赖氨酸残基的分子内Ag（i）促进反应，生成Lys-Asp（或Asp-Lys）侧链内酰胺桥联肽，无需耦合剂。

  DOI：

  10.1039/d1ob02461b
• 作为产物：
  描述：

  Nε-Boc-Nα-Cbz-L-赖氨酸 、 L-丙氨酸甲酯盐酸盐 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以92%的产率得到Cbz-Lys(Boc)-Ala-OMe
  参考文献：
  名称：

  A conformationally constrained fused tricyclic nisin AB-ring system mimic toward an improved pyrophosphate binder of lipid II

  摘要：

  The bacteria-specific membrane component lipid Ills essential for bacterial cell wall synthesis. A tricyclic nisin mimic was designed and synthesized in which both thioether moieties were mimicked by an alkane-bridge, as well as the introduction of a third conformational constraint consisting of a macrocyclic lactam-bridge between the N-terminus and the B-ring. The newly designed tricyclic AB-ring mimic was found to bind lipid II since it was able to inhibit nisin-induced membrane leakage in a dose-dependent manner. These results imply that the tricyclic AB-ring mimic may form a novel class of lead structures for the development of nisin-based peptide antibiotics. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.06.023

文献信息

• Transesterifications with 1,8-Diazabicyclo[5.4.0]undec-7-ene/Lithium Bromide (DBU/LiBr) - Also Applicable to Cleavage of Peptides from Resins inMerrifleld Syntheses
  作者：Dieter Scebach、Adrian Thaler、Denis Blaser、Soo Y. Ko

  DOI：10.1002/hlca.19910740520

  日期：1991.8.7

  amidine base 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and LiBr (preferably 0,5 and 5 equiv., resp.) turns out to be a highly efficient catalyst (at 0–25°) for saponifications (in THF/H2O) and transesterifications (in ROH). The scope and limitations of the method are determined using ca. two dozens of different ester/alcohol combinations (Schemes 2 and 3). The investigation is focused on peptides as substrates

  base碱的1,8-二氮杂双环[5.4.0]十一碳-7-烯（DBU）和LiBr（最好分别为0.5和5当量）的混合物被证明是一种高效催化剂（0时） –25°）用于皂化（在THF / H 2 O中）和酯交换（在ROH中）。该方法的范围和局限性由ca确定。两种不同的酯/醇组合（方案2和3）。研究集中在肽作为底物上。在精心控制的条件下，N -Boc-和N不会发生准分子反应-Z-保护的肽酯，当是甲基，乙基，异丙基或烯丙基酯的产物时，如含多达六个氨基酸的肽所示，C端带有Ala，Len MeLeu，Asp（OEt）或Tyr （方案3以及表1和2）。Bom-Leu-Ala-Gly-Val-OR和Boc-Leu-Ala-Gly-Phe-OR（R = H，Me）从PAM和Wang树脂中水解和酯基转移（R = H，Me）（0–25°下1–8 h ，通过这种方法可以在不致使C端立体异构中心发生差向异构的情况下，获
• GEM-DIFLUORIDE C-GLYCOPEPTIDE COMPOUNDS, THEIR PREPARATION AND USE PARTICULARLY FOR PRESERVATION OF BIOLOGICAL MATERIALS
  申请人：Castelot Deliencourt-Godefroy Géraldine

  公开号：US20090311203A1

  公开（公告）日：2009-12-17

  The invention relates to a gem-difluoride C-glycopeptide compound with formula I where n is an integer equal to 3 or 4, R represents a hydrogen atom, an alkyl, benzyl, acetyl, trimethylsilyl, tert-butyldimethylsilyl, tert-butyldiphenylsilyl group, R′ represents OR, NR′R″, N 3 , or a phthalimide, R′ and R″ represent a hydrogen atom or an alkyl, aryl, benzyl, benzoyl, acetyl, alkyloxycarbonyl, allyloxycarbonyl, benzyloxycarbonyl group, R1 represents a hydrogen atom or an alkyl, benzyl, alkylcarbamate, allylcarbamate, benzylcarbamate, acetyl group, R 1 may consist of an amino acid if R 2 represents only OR, R 2 includes an amino acid if R 1 represents a hydrogen atom or an alkyl, benzyl, alkylcarbamate, allylcarbamate, benzylcarbamate, acetyl group, R 2 represents OR when R 1 represents an amino acid, R 3 represents a hydrogen atom or a free or protected alcohol function. It is applicable to the preparation of compounds or compositions to be used for preservation of biological materials such as cells, tissues and organs at various temperatures.
• A conformationally constrained fused tricyclic nisin AB-ring system mimic toward an improved pyrophosphate binder of lipid II
  作者：Rianne A.G. Harmsen、Nourdin Ghalit、Johan Kemmink、Eefjan Breukink、Rob M.J. Liskamp、Dirk T.S. Rijkers

  DOI：10.1016/j.tet.2014.06.023

  日期：2014.10

  The bacteria-specific membrane component lipid Ills essential for bacterial cell wall synthesis. A tricyclic nisin mimic was designed and synthesized in which both thioether moieties were mimicked by an alkane-bridge, as well as the introduction of a third conformational constraint consisting of a macrocyclic lactam-bridge between the N-terminus and the B-ring. The newly designed tricyclic AB-ring mimic was found to bind lipid II since it was able to inhibit nisin-induced membrane leakage in a dose-dependent manner. These results imply that the tricyclic AB-ring mimic may form a novel class of lead structures for the development of nisin-based peptide antibiotics. (C) 2014 Elsevier Ltd. All rights reserved.
• Backbone thioamide directed macrocyclisation: lactam stapling of peptides
  作者：Ameer B. Taresh、Craig A. Hutton

  DOI：10.1039/d1ob02461b

  日期：——

  The intramolecular Ag(i)-promoted reaction of peptide thioamides containing Asp and Lys residues generates the Lys–Asp (or Asp–Lys) side-chain lactam bridged peptides without requirement of a coupling agent.

  肽硫酰胺中含有天冬氨酸和赖氨酸残基的分子内Ag（i）促进反应，生成Lys-Asp（或Asp-Lys）侧链内酰胺桥联肽，无需耦合剂。