(tert-butoxycarbonyl)(N-(4-(3-(trifluoromethyl)-3H-diazirin-3-yl)benzoyl)sulfamoyl)-D-alanine | 1116151-71-3

• 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: (tert-butoxycarbonyl)(N-(4-(3-(trifluoromethyl)-3H-diazirin-3-yl)benzoyl)sulfamoyl)-D-alanine
• CAS: 1116151-71-3
• 化学式: C₁₇H₁₉F₃N₄O₇S
• 分子量: 480.422
• InChiKey: XTLBVTIQYGSJHN-NSHDSACASA-N

物化性质

• 密度：
  1.57±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  32.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  163.59
• 氢给体数：
  3.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (tert-butoxycarbonyl)(N-(4-(3-(trifluoromethyl)-3H-diazirin-3-yl)benzoyl)sulfamoyl)-D-alanine 、 N-生物素-3,6-二氧杂辛烷-1,8-二胺 在 N-羟基-7-氮杂苯并三氮唑 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以72%的产率得到tert-butyl ((R)-3,14-dioxo-18-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)-1-(N-(4-(3-(trifluoromethyl)-3H-diazirin-3-yl)benzoyl)sulfamoyl)-7,10-dioxa-4,13-diazaoctadecan-2-yl)carbamate
  参考文献：
  名称：

  Synthesis and evaluation of novel photoreactive α-amino acid analog carrying acidic and cleavable functions

  摘要：

  A novel photoreactive alpha-amino acid bearing an acidic residue and a cleavable diazirine was developed. To mimic common acidic alpha-amino acids, the residue was designed to be N-acylsulfonamide that possesses an acidic proton and is able to dissociate under the physiological conditions. The inhibition assay of its biotin-tagged derivative with glutamyl endopeptidase from Staphylococcus aureus V8 strain revealed a Ki(app) value of 162 mu M, which is slightly higher than the K-m value of a common substrate. Upon UV irradiation, this derivative specifically photolabeled glutamyl endopeptidase, L-glutamate dehydrogenase, glutamic oxalacetic transaminase, and L-glutamine synthetase, all the enzymes exhibit high affinity toward acidic alpha-amino acids. In addition, N-acylsulfonamide group functioned as a cleavable linker in mild basic solution after a brief N-alkylation. Either the multifunctional nature or the simple structure of this acidic alpha-amino acid surrogate would be useful as versatile photoreactive building block. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.11.013
• 作为产物：
  描述：

  C₁₈H₂₁F₃N₄O₇S 在 sodium hydroxide 、 水 作用下， 以 甲醇 为溶剂， 以96%的产率得到(tert-butoxycarbonyl)(N-(4-(3-(trifluoromethyl)-3H-diazirin-3-yl)benzoyl)sulfamoyl)-D-alanine
  参考文献：
  名称：

  Synthesis and evaluation of novel photoreactive α-amino acid analog carrying acidic and cleavable functions

  摘要：

  A novel photoreactive alpha-amino acid bearing an acidic residue and a cleavable diazirine was developed. To mimic common acidic alpha-amino acids, the residue was designed to be N-acylsulfonamide that possesses an acidic proton and is able to dissociate under the physiological conditions. The inhibition assay of its biotin-tagged derivative with glutamyl endopeptidase from Staphylococcus aureus V8 strain revealed a Ki(app) value of 162 mu M, which is slightly higher than the K-m value of a common substrate. Upon UV irradiation, this derivative specifically photolabeled glutamyl endopeptidase, L-glutamate dehydrogenase, glutamic oxalacetic transaminase, and L-glutamine synthetase, all the enzymes exhibit high affinity toward acidic alpha-amino acids. In addition, N-acylsulfonamide group functioned as a cleavable linker in mild basic solution after a brief N-alkylation. Either the multifunctional nature or the simple structure of this acidic alpha-amino acid surrogate would be useful as versatile photoreactive building block. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.11.013