Z-L-Lys(Boc)-L-Lys(Boc)-OH | 47846-88-8

• 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: Z-L-Lys(Boc)-L-Lys(Boc)-OH
• 英文别名: Z-Lys(Boc)-Lys(Boc)-OH；Cbz-Lys(Boc)-Lys(Boc)-OH；(2S)-6-[(2-methylpropan-2-yl)oxycarbonylamino]-2-[[(2S)-6-[(2-methylpropan-2-yl)oxycarbonylamino]-2-(phenylmethoxycarbonylamino)hexanoyl]amino]hexanoic acid
• CAS: 47846-88-8
• 化学式: C₃₀H₄₈N₄O₉
• 分子量: 608.733
• InChiKey: YINOJXLJXHYPOC-GOTSBHOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  43
• 可旋转键数：
  21
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  181
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  Z-L-Lys(Boc)-L-Lys(Boc)-OH 在 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 18.25h， 生成 Cbz-Lys-Lys-PABC-AMC*2TFA
  参考文献：
  名称：

  Prodrug-Inspired Probes Selective to Cathepsin B over Other Cysteine Cathepsins

  摘要：

  Cathepsin B (CTB) is a cysteine protease believed to be an important therapeutic target or biomarker for several diseases including aggressive cancer, arthritis, and parasitic infections. The development of probes capable of assessing CTB activity in cell lysates, living cells, and animal models of disease are needed to understand its role in disease progression. However, discovering probes selective to cathepsin B over other cysteine cathepsins is a significant challenge due to overlap of preferred substrates and binding site homology in this family of proteases. Herein we report the synthesis and detailed evaluation of two prodrug-inspired fluorogenic peptides designed to be efficient and selective substrate-based probes for CTB. Through cell lysate and cell assays, a promising lead candidate was identified that is efficiently processed and has high specificity for CTB over other cysteine cathepsins. This work represents a key step toward the design of rapid release prodrugs or substrate-based molecular imaging probes specific to CTB.

  DOI：

  10.1021/jm500544p
• 作为产物：
  描述：

  (S)-2-amino-6-(tert-butoxycarbonylamino)hexanoic acid 在 盐酸 作用下， 反应 48.0h， 生成 Z-L-Lys(Boc)-L-Lys(Boc)-OH
  参考文献：
  名称：

  Synthesis of a modified fragment 13?19 of the sequence of ACTH using silyl protection

  摘要：

  DOI：

  10.1007/bf00567293

文献信息

• Use of pentafluorophenyl esters in the synthesis of intermediate fragments of ACTH
  作者：V. N. Karel'skii、E. P. Krysin、A. A. Antonov、G. E. Rostovskaya

  DOI：10.1007/bf00581604

  日期：1982.1
• Synthese von Konjugaten des Heptalysins mit Penicillinen
  作者：Eugen SCHNABEL

  DOI：10.1515/bchm2.1976.357.2.1365

  日期：1976.1
• [EN] CATHEPSIN B-TARGETING PROBES<br/>[FR] SONDES DE CIBLAGE DE LA CATHEPSINE B
  申请人：THUNDER BAY REGIONAL RES INST

  公开号：WO2015123783A1

  公开（公告）日：2015-08-27

  Compounds that are cathepsin B substrates and that are useful as imaging probes, for example in positron emission tomography (PET) or fluorescence imaging are described.