Cbz-Lys(N-Boc)-Ala-OH | 95930-16-8

• 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(N-Boc)-Ala-OH
• 英文别名: N^α-benzyloxycarbonyl-N^ε-t-butoxycarbonyl-L-lysyl-L-alanine；Cbz-Lys(Boc)-Ala-OH
• CAS: 95930-16-8
• 化学式: C₂₂H₃₃N₃O₇
• 分子量: 451.52
• InChiKey: BZPVELNOMQSMAM-RDJZCZTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.57
• 重原子数：
  32.0
• 可旋转键数：
  11.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  143.06
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  Cbz-Lys(N-Boc)-Ala-OH 在 盐酸 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三乙胺 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 生成 Cbz-Lys-Ala-Sta-NHcHex
  参考文献：
  名称：

  Transition State Mimetics of the Plasmodium Export Element Are Potent Inhibitors of Plasmepsin V from P. falciparum and P. vivax

  摘要：

  Following erythrocyte invasion, malaria parasites export a catalogue of remodeling proteins into the infected cell that enable parasite development in the human host. Export is dependent on the activity of the aspartyl protease, plasmepsin V (PMV), which cleaves proteins within the Plasmodium export element (PEXEL; RxL down arrow xE/Q/D) in the parasite's endoplasmic reticulum. Here, we generated transition state mimetics of the native PEXEL substrate that potently inhibit PMV isolated from Plasmodium falciparum and Plasmodium vivax. Through optimization, we identified that the activity of the mimetics was completely dependent on the presence of P-1 Leu and P-3 Arg. Treatment of P. falciparum-infected erythrocytes with a set of optimized mimetics impaired PEXEL processing and killed the parasites. The striking effect of the compounds provides a clearer understanding of the accessibility of the PMV active site and reaffirms the enzyme as an attractive target for the design of future antimalarials.

  DOI：

  10.1021/jm500797g
• 作为产物：
  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

文献信息

• Nagao, Yoshimitsu; Miyasaka, Tadayo; Seno, Kaoru, Journal of the Chemical Society. Perkin transactions I, 1984, p. 2439 - 2446
  作者：Nagao, Yoshimitsu、Miyasaka, Tadayo、Seno, Kaoru、Fujita, Eiichi、Shibata, Daisuke、Doi, Etsushiro

  DOI：——

  日期：——
• 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.