(S)-2-(Benzhydrylidene-amino)-3-[8-(tert-butyl-diphenyl-silanyloxy)-5-dimethylsulfamoyl-quinolin-2-yl]-propionic acid tert-butyl ester | 607708-60-1

• 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: (S)-2-(Benzhydrylidene-amino)-3-[8-(tert-butyl-diphenyl-silanyloxy)-5-dimethylsulfamoyl-quinolin-2-yl]-propionic acid tert-butyl ester
• CAS: 607708-60-1
• 化学式: C₄₇H₅₁N₃O₅SSi
• 分子量: 798.091
• InChiKey: ANTZRDMUGGOWRP-FAIXQHPJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.21
• 重原子数：
  57.0
• 可旋转键数：
  12.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  98.16
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (S)-2-(Benzhydrylidene-amino)-3-[8-(tert-butyl-diphenyl-silanyloxy)-5-dimethylsulfamoyl-quinolin-2-yl]-propionic acid tert-butyl ester 在 盐酸 、 碳酸氢钠 作用下， 以 1,4-二氧六环 为溶剂， 反应 20.0h， 生成 (S)-2-amino-N^α-(9-fluorenylmethyloxycarbonyl)-3-(8-hydroxy-5-(N,N-dimethyl)sylfonamidoquinoline-2-yl)propionic acid
  参考文献：
  名称：

  Modular and Tunable Chemosensor Scaffold for Divalent Zinc

  摘要：

  A modular peptide scaffold has been developed for fluorescent sensing of divalent zinc. The signaling component of the chemosensor is the chelation -sensitive fluorophore 8-hydroxy-5-(N,N-dimethylsulfonamido)-2-methylquinoline, which is prepared as the protected amino acid derivative Fmoc-Sox-OH and integrated into peptide sequences. Nineteen synthetic peptides incorporating the signaling element exhibit a range of affinities for Zn2+ through variation of the type and number of Zn2+ ligands, ligand arrangement and the beta-turn sequence that acts as a preorganization element between the ligands. The stoichiometry of the peptide-Zn2+ complexes is evaluated by several criteria. The fluorescence response of these peptides to pH and various important metal ions is reported. Eleven of these sequences form only 1:1 complexes with Zn2+ and their affinities range from 10 nM to nearly 1 muM. When used in concert, these sensors can provide Zn2+ concentration information in a valuable range.

  DOI：

  10.1021/ja0355980
• 作为产物：
  描述：

  8-tert-butyldiphenylsilyloxy-5-(N,N-dimethyl)sulfonamide-2-methylquinoline 在 sodium tetrahydroborate 、 N-溴代丁二酰亚胺(NBS) 、 selenium(IV) oxide 、 O-烯丙基-N-(9-蒽甲基)溴化金鸡纳碱 、 4 A molecular sieve 、 cesium hydrochloride monohydrate 、 三苯基膦 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 为溶剂， 反应 72.25h， 生成 (S)-2-(Benzhydrylidene-amino)-3-[8-(tert-butyl-diphenyl-silanyloxy)-5-dimethylsulfamoyl-quinolin-2-yl]-propionic acid tert-butyl ester
  参考文献：
  名称：

  Modular and Tunable Chemosensor Scaffold for Divalent Zinc

  摘要：

  A modular peptide scaffold has been developed for fluorescent sensing of divalent zinc. The signaling component of the chemosensor is the chelation -sensitive fluorophore 8-hydroxy-5-(N,N-dimethylsulfonamido)-2-methylquinoline, which is prepared as the protected amino acid derivative Fmoc-Sox-OH and integrated into peptide sequences. Nineteen synthetic peptides incorporating the signaling element exhibit a range of affinities for Zn2+ through variation of the type and number of Zn2+ ligands, ligand arrangement and the beta-turn sequence that acts as a preorganization element between the ligands. The stoichiometry of the peptide-Zn2+ complexes is evaluated by several criteria. The fluorescence response of these peptides to pH and various important metal ions is reported. Eleven of these sequences form only 1:1 complexes with Zn2+ and their affinities range from 10 nM to nearly 1 muM. When used in concert, these sensors can provide Zn2+ concentration information in a valuable range.

  DOI：

  10.1021/ja0355980