acetoxymethyl-4-methylumbelliferone

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: acetoxymethyl-4-methylumbelliferone
• 英文别名: AMMU；((4-Methyl-2-oxo-2H-chromen-7-yl)oxy)methyl acetate；(4-methyl-2-oxochromen-7-yl)oxymethyl acetate
• 化学式: C₁₃H₁₂O₅
• 分子量: 248.235
• InChiKey: HWDPFCMANRSJNK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  羟甲香豆素 、 (bromomethoxy)methyl acetate 在 N,N-二异丙基乙胺 、 苄胺 作用下， 以 N,N-二甲基甲酰胺 、 氯仿 为溶剂， 反应 16.0h， 以18%的产率得到acetoxymethyl-4-methylumbelliferone
  参考文献：
  名称：

  针对碳水化合物酯酶家族4脱N-乙酰酶的单糖抑制剂

  摘要：

  碳水化合物酯酶家族4包含可改变肽聚糖和生物膜相关胞外多糖的毒力因子。尽管该酶家族很重要，但基于机理的有效抑制策略尚未出现。基于假定的四面体脱-N-乙酰化中间体的三齿结合模式，合成了在2和3位带有金属螯合基团的GlcNAc衍生物。这些支架包括2-C膦酸酯，2-C磺酰胺，2-硫代乙酰胺弹头以及在3-位带有巯基，胺和叠氮化物取代基的衍生物。对这些抑制剂针对代表性的肽聚糖脱乙酰酶（来自肺炎链球菌肺炎的Pgda）进行了测定，和代表性的生物膜相关胞外多糖脱乙酰基酶，PgaB从大肠杆菌。在评估的抑制剂中，3-硫代衍生物对Pgda的抑制作用弱到中等。最强的抑制剂是2,3-二甲氧基苄基-2-硫代乙酰胺-3-硫代-β- d-葡萄糖苷，其抑制能力显示出对金属浓度的出乎意料的依赖性，并且发现其具有部分混合抑制模式（K i  = 2.9 ±0.6μM）。

  DOI：

  10.1016/j.bmc.2018.10.008

文献信息

• BRET SENSOR MOLECULES FOR DETECTING HYDROLASES
  申请人：Commonwealth Scientific and Industrial Research Organisation

  公开号：US20210018497A1

  公开（公告）日：2021-01-21

  The present invention relates to bioluminescence resonance energy transfer sensor molecules having the structure R 1 -L-R 2 —B or B—R 2 -L-R 1 , wherein R 1 is a bioluminescent protein, L is a linking element, R 2 is a non-protein acceptor domain and B is a blocking group, and wherein R 2 bound to B comprises a hydrolysable bond which produces a change in BRET when hydrolysed. The invention also discloses a method of detecting a hydrolase by contacting a sample with a molecule B—R 2 , then contacting with a compound R 1 -L or L-R 1 under conditions to cause attaching of R 2 to L, and detecting a change in the BRET ratio. Specifically exemplified sensors comprise luciferase and fluorescein diacetate, which is hydrolysed by an esterase. The invention also discloses luciferase enzymes derived from RLuc8 by removing cysteine residues.
• [EN] BRET SENSOR MOLECULES FOR DETECTING HYDROLASES<br/>[FR] MOLÉCULES DE DÉTECTION DE BRET POUR LA DÉTECTION D'HYDROLASES
  申请人：COMMW SCIENT IND RES ORG

  公开号：WO2019036769A1

  公开（公告）日：2019-02-28

  The present invention relates to bioluminescence resonance energy transfer sensor molecules having the structure R1-L-R2 -B or B- R2-L-R1, wherein R1 is a bioluminescent protein, L is a linking element, R2 is a non-protein acceptor domain and B is a blocking group, and wherein R2 bound to B comprises a hydrolysable bond which produces a change in BRET when hydrolysed. The invention also discloses a method of detecting a hydrolase by contacting a sample with a molecule B-R2, then contacting with a compound R1-L or L-R1 under conditions to cause attaching of R2 to L, and detecting a change in the BRET ratio. Specifically exemplified sensors comprise luciferase and fluorescein diacetate, which is hydrolysed by an esterase. The invention also discloses luciferase enzymes derived from RLuc8 by removing cysteine residues.