glycine-7-amino-4-methylcoumarin

• 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: glycine-7-amino-4-methylcoumarin
• 英文别名: glycine (4-methylcoumarin-7-yl)amide；7-(glycylamino)-4-methylcoumarin；L-Gly-AMC；Gly-AMC；2-Amino-N-(4-methyl-2-oxo-2H-chromen-7-yl)acetamide；2-amino-N-(4-methyl-2-oxochromen-7-yl)acetamide
• 化学式: C₁₂H₁₂N₂O₃
• 分子量: 232.239
• InChiKey: KYIPWSXYZXKCST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  81.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  glycine-7-amino-4-methylcoumarin 、 BOC-L-苯丙氨酸 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.25h， 以44%的产率得到
  参考文献：
  名称：

  Development of fluorescent peptide substrates and assays for the key autophagy-initiating cysteine protease enzyme, ATG4B

  摘要：

  An efficient assay for monitoring the activity of the key autophagy-initiating enzyme ATG4B based on a small peptide substrate has been developed. A number of putative small fluorogenic peptide substrates were prepared and evaluated and optimized compounds showed reasonable rates of cleavage but required high enzyme concentrations which limited their value. A modified peptide substrate incorporating a less sterically demanding self-immolative element was designed and synthesized and was shown to have enhanced properties useful for evaluating inhibitors of ATG4B. Substrate cleavage was readily monitored and was linear for up to 4 h but enzyme concentrations of about ten-fold higher were required compared to assays using protein substrate LC3 or analogs thereof (such as FRET-LC3). Several known inhibitors of ATG4B were evaluated using the small peptide substrate and gave IC50 values 3-7 fold higher than previously obtained values using the FRET-LC3 substrate. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.04.064
• 作为产物：
  描述：

  Boc-Gly-AMC 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以95%的产率得到glycine-7-amino-4-methylcoumarin
  参考文献：
  名称：

  通过肽酰肼的化学合成Ub-AMC

  摘要：

  泛素与7-氨基-4-甲基香豆素（Ub-AMC）的C末端缀合物是基于荧光的去泛素化酶（DUB）活性分析的重要探针。开发更有效的方法来制备Ub-AMC非常重要，因为当前可用的技术对于大规模生产仍然很昂贵。在本工作中，我们报告了通过肽酰肼的连接进行Ub-AMC全化学合成的有效策略。通过N-C顺序连接组装三个肽段，并通过TCEP介导的脱硫将所得产物转化为Ub-AMC。合成的Ub-AMC通过测量其DUB活性显示具有预期的生物学功能。

  DOI：

  10.1007/s11426-013-4885-x

文献信息

• Late Transition Metal Complexes of a Coumarin-Functionalized Ditertiary Phosphine
  作者：Mark R. J. Elsegood、Andrew J. Lake、Claire L. Elliott、Martin B. Smith、George W. Weaver

  DOI：10.1080/10426500701735536

  日期：2008.1.14

  The synthesis of a new coumarin-modified ditertiary phosphine is reported along with three square-planar PdII and PtII complexes. All compounds have been characterised by 31P1H and 1H NMR spectroscopy, FT–IR spectroscopy and microanalysis. Furthermore a single crystal X-ray structure determination of one of these complexes has been undertaken.

  报道了一种新的香豆素修饰的二叔膦以及三个方形平面 PdII 和 PtII 复合物的合成。所有化合物均已通过 31P1H 和 1H NMR 光谱、FT-IR 光谱和微量分析进行表征。此外，已经对这些配合物之一进行了单晶 X 射线结构测定。
• Novel chromophore containing compounds
  申请人：MERCK & CO. INC.

  公开号：EP0528487A2

  公开（公告）日：1993-02-24

  Disclosed are novel chromophore containing compounds of Formula I and their use in determining interleukin-1β convertase (ICE) activity. ICE has been implicated in inflammatory or immune-based diseases of the lung and airways; central nervous system and surrounding membranes; the eyes and ears; joints, bones, and connective tissues; cardiovascular system including the pericardium; the gastrointestinal and urogenital systems; the skin and mucosal membranes.

  本发明公开了含有式 I 的新型发色团化合物及其在测定白细胞介素-1β 转化酶（ICE）活性中的用途。白细胞介素-1β转换酶与以下部位的炎症性或免疫性疾病有关：肺和呼吸道；中枢神经系统和周围的膜；眼睛和耳朵；关节、骨骼和结缔组织；心血管系统，包括心包；胃肠道和泌尿生殖系统；皮肤和粘膜。
• TOTAL CHEMICAL SYNTHESIS OF UBIQUITIN, UBIQUITIN MUTANTS AND DERIVATIVES THEREOF
  申请人：Stichting Het Nederlands Kanker Instituut

  公开号：EP2616479A1

  公开（公告）日：2013-07-24
• JPH05255388A
  申请人：——

  公开号：JPH05255388A

  公开（公告）日：1993-10-05
• US6348570B1
  申请人：——

  公开号：US6348570B1

  公开（公告）日：2002-02-19