γ-O-desyl tert-butyl N-t-BOC-glutamate

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: γ-O-desyl tert-butyl N-t-BOC-glutamate
• 英文别名: 1-O-tert-butyl 5-O-(2-oxo-1,2-diphenylethyl) (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanedioate
• 化学式: C₂₈H₃₅NO₇
• 分子量: 497.588
• InChiKey: OOINBTJBSKMRTJ-XEGCMXMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  36
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  γ-O-desyl tert-butyl N-t-BOC-glutamate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以52%的产率得到γ-O-desyl glutamate
  参考文献：
  名称：

  Desyl Esters of Amino Acid Neurotransmitters. Phototriggers for Biologically Active Neurotransmitters

  摘要：

  The application of the desyl or 2-oxo-1,2-diphenylethyl moiety as a photolabile ligand for the release of phosphates such as cAMP and inorganic phosphate (P-i)(1,2) is extended to include selected excitatory amino acids. The synthesis and photochemical studies of N- and O-desyl-caged Versions of the endogenous amino acid neurotransmitters glutamate and gamma-aminobutyric acid (GABA) are reported. Photolysis at 350 nm of solutions of gamma-O-desyl glutamate (11) and O-desyl GABA (14) in 1:1 H2O-acetonitrile cleanly produced free glutamate and GABA, respectively, with rate constants of ca. 10(7) s(-1); 2-phenylbenzo[b]furan (2) was the only photobyproduct detected by HPLC. Photolysis quantum efficiencies for the disappearance of O-desyl amino acid esters were in the range of 0.29-0.31, and the appearance efficiencies of furan 2 (and the corresponding amino acid) were 0.14. The photolysis of 14 was efficiently quenched with sodium 2-naphthalenesulfonate, yielding a triplet lifetime of ca. 10 ns. Photolysis of 11 in mammalian brain tissue slices resulted in glutamate receptor activation, as indicated by whole cell electrophysiological measurements. Photolysis of the other desyl amino acids resulted in decomposition and produced several products but did not lead to the formation of furan 2.

  DOI：

  10.1021/jo951635x
• 作为产物：
  描述：

  Boc-L-谷氨酸-1-叔丁酯 、 2-溴-2-苯基乙酰苯 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 苯 为溶剂， 以96%的产率得到γ-O-desyl tert-butyl N-t-BOC-glutamate
  参考文献：
  名称：

  Desyl Esters of Amino Acid Neurotransmitters. Phototriggers for Biologically Active Neurotransmitters

  摘要：

  The application of the desyl or 2-oxo-1,2-diphenylethyl moiety as a photolabile ligand for the release of phosphates such as cAMP and inorganic phosphate (P-i)(1,2) is extended to include selected excitatory amino acids. The synthesis and photochemical studies of N- and O-desyl-caged Versions of the endogenous amino acid neurotransmitters glutamate and gamma-aminobutyric acid (GABA) are reported. Photolysis at 350 nm of solutions of gamma-O-desyl glutamate (11) and O-desyl GABA (14) in 1:1 H2O-acetonitrile cleanly produced free glutamate and GABA, respectively, with rate constants of ca. 10(7) s(-1); 2-phenylbenzo[b]furan (2) was the only photobyproduct detected by HPLC. Photolysis quantum efficiencies for the disappearance of O-desyl amino acid esters were in the range of 0.29-0.31, and the appearance efficiencies of furan 2 (and the corresponding amino acid) were 0.14. The photolysis of 14 was efficiently quenched with sodium 2-naphthalenesulfonate, yielding a triplet lifetime of ca. 10 ns. Photolysis of 11 in mammalian brain tissue slices resulted in glutamate receptor activation, as indicated by whole cell electrophysiological measurements. Photolysis of the other desyl amino acids resulted in decomposition and produced several products but did not lead to the formation of furan 2.

  DOI：

  10.1021/jo951635x

文献信息

• Desyl Esters of Amino Acid Neurotransmitters. Phototriggers for Biologically Active Neurotransmitters
  作者：Kyle R. Gee、L. William Kueper、Jeffrey Barnes、Gregory Dudley、Richard S. Givens

  DOI：10.1021/jo951635x

  日期：1996.1.1

  The application of the desyl or 2-oxo-1,2-diphenylethyl moiety as a photolabile ligand for the release of phosphates such as cAMP and inorganic phosphate (P-i)(1,2) is extended to include selected excitatory amino acids. The synthesis and photochemical studies of N- and O-desyl-caged Versions of the endogenous amino acid neurotransmitters glutamate and gamma-aminobutyric acid (GABA) are reported. Photolysis at 350 nm of solutions of gamma-O-desyl glutamate (11) and O-desyl GABA (14) in 1:1 H2O-acetonitrile cleanly produced free glutamate and GABA, respectively, with rate constants of ca. 10(7) s(-1); 2-phenylbenzo[b]furan (2) was the only photobyproduct detected by HPLC. Photolysis quantum efficiencies for the disappearance of O-desyl amino acid esters were in the range of 0.29-0.31, and the appearance efficiencies of furan 2 (and the corresponding amino acid) were 0.14. The photolysis of 14 was efficiently quenched with sodium 2-naphthalenesulfonate, yielding a triplet lifetime of ca. 10 ns. Photolysis of 11 in mammalian brain tissue slices resulted in glutamate receptor activation, as indicated by whole cell electrophysiological measurements. Photolysis of the other desyl amino acids resulted in decomposition and produced several products but did not lead to the formation of furan 2.