(S)-2-(Benzhydrylidene-amino)-3-(10-cyano-anthracen-9-yl)-propionic acid tert-butyl ester | 184962-83-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: (S)-2-(Benzhydrylidene-amino)-3-(10-cyano-anthracen-9-yl)-propionic acid tert-butyl ester
• 英文别名: tert-butyl (2S)-2-(benzhydrylideneamino)-3-(10-cyanoanthracen-9-yl)propanoate
• CAS: 184962-83-2
• 化学式: C₃₅H₃₀N₂O₂
• 分子量: 510.635
• InChiKey: LTNLXGBACIBJSA-YTTGMZPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  39
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  62.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  9-芴甲基-N-琥珀酰亚胺基碳酸酯 、 (S)-2-(Benzhydrylidene-amino)-3-(10-cyano-anthracen-9-yl)-propionic acid tert-butyl ester 在 盐酸 、 sodium carbonate 作用下， 生成 (S)-3-(10-Cyano-anthracen-9-yl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid
  参考文献：
  名称：

  New Synthetic Amino Acids for the Design and Synthesis of Peptide-Based Metal Ion Sensors

  摘要：

  The syntheses of two new nonstandard amino acids, Flu (6) and YBp (20), and a new synthesis of Dmd (12) are reported. These residues exhibit fluorescence, metal-coordination, and fluorescence-quenching properties, respectively. These building blocks have been incorporated into peptides via solid phase peptide synthesis to afford the prototype fur a photoinduced electron transfer-based metal ion chemosensor. The fluorescence of the peptides is modulated upon metal binding. This results from a metal. ion-induced conformational change that brings the side chains of the Flu and Dmd amino acids into proximity, thereby favoring photoinduced electron transfer (PET) fluorescence quenching.

  DOI：

  10.1021/jo961466w
• 作为产物：
  描述：

  10-甲基蒽-9-甲醛 在 sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 、 羟胺 、 乙酸酐 、 N-苄基氯化辛可宁丁 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 28.67h， 生成 (S)-2-(Benzhydrylidene-amino)-3-(10-cyano-anthracen-9-yl)-propionic acid tert-butyl ester
  参考文献：
  名称：

  New Synthetic Amino Acids for the Design and Synthesis of Peptide-Based Metal Ion Sensors

  摘要：

  The syntheses of two new nonstandard amino acids, Flu (6) and YBp (20), and a new synthesis of Dmd (12) are reported. These residues exhibit fluorescence, metal-coordination, and fluorescence-quenching properties, respectively. These building blocks have been incorporated into peptides via solid phase peptide synthesis to afford the prototype fur a photoinduced electron transfer-based metal ion chemosensor. The fluorescence of the peptides is modulated upon metal binding. This results from a metal. ion-induced conformational change that brings the side chains of the Flu and Dmd amino acids into proximity, thereby favoring photoinduced electron transfer (PET) fluorescence quenching.

  DOI：

  10.1021/jo961466w

文献信息

• New Synthetic Amino Acids for the Design and Synthesis of Peptide-Based Metal Ion Sensors
  作者：Alicia Torrado、Barbara Imperiali

  DOI：10.1021/jo961466w

  日期：1996.1.1

  The syntheses of two new nonstandard amino acids, Flu (6) and YBp (20), and a new synthesis of Dmd (12) are reported. These residues exhibit fluorescence, metal-coordination, and fluorescence-quenching properties, respectively. These building blocks have been incorporated into peptides via solid phase peptide synthesis to afford the prototype fur a photoinduced electron transfer-based metal ion chemosensor. The fluorescence of the peptides is modulated upon metal binding. This results from a metal. ion-induced conformational change that brings the side chains of the Flu and Dmd amino acids into proximity, thereby favoring photoinduced electron transfer (PET) fluorescence quenching.