N-benzyloxycarbonyl-L-alanine-L-tryptophan ethyl ester | 218799-33-8

• 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: N-benzyloxycarbonyl-L-alanine-L-tryptophan ethyl ester
• 英文别名: ethyl (2S)-3-(1H-indol-3-yl)-2-[[(2S)-2-(phenylmethoxycarbonylamino)propanoyl]amino]propanoate
• CAS: 218799-33-8
• 化学式: C₂₄H₂₇N₃O₅
• 分子量: 437.495
• InChiKey: OIQJMWHFFPPFGL-KKSFZXQISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  110
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-benzyloxycarbonyl-L-alanine-L-tryptophan ethyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以93%的产率得到L-alanyl-L-tryptophan ethyl ester
  参考文献：
  名称：

  Long-Lived Charge-Separated Species Observed on Flash Photolysis of Peptide Conjugates. Interplay of Local and Radical Ion Pair Triplet States¹

  摘要：

  Peptides composed of alanine (Ala) and tryptophan (Trp), modified with the (nitro)pyrenesulfonyl chromophore (Pyr and NPyr) at the N-terminus have been examined by nanosecond laser flash photolysis. A common phototransient for Pyr-AlaOEt and Pyr-Ala-TrpOEt was observed that exhibited broad absorption at 410-550 nm and decay time constants in the range, tau(1/2) = 20-40 mu s. This species was assigned to the triplet excited state that is local to the pyrene chromophore ((3)Pyr). For the conjugates having a stronger electron acceptor group at the N-terminus, NPyr-Ala-TrpOEt and NPyr-Ala-Ala-TrpOEt, the local triplet was replaced with a phototransient whose principal feature is a sharp band at 440 nm (assigned to the NPyr(-.) radical anion). The radical ion transients for the NPyr peptide derivatives were assigned to intermediates that result from the intramolecular electron transfer quenching of NP excited species by pendant groups (i.e., the indole ring of tryptophan). The lifetimes observed for the radical ion transients associated with the NPyr series were relatively long (extending to ca. 400 ns) and depended in an interesting way on the structure of the peptide linkage. A mechanism of electron transfer in the singlet manifold and recombination yielding a local Pyr triplet state is important for the Pyr series.

  DOI：

  10.1021/jo981241g
• 作为产物：
  描述：

  苄氧羰基-L-丙氨酸 在 吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 乙酸乙酯 为溶剂， 反应 1.0h， 生成 N-benzyloxycarbonyl-L-alanine-L-tryptophan ethyl ester
  参考文献：
  名称：

  Long-Lived Charge-Separated Species Observed on Flash Photolysis of Peptide Conjugates. Interplay of Local and Radical Ion Pair Triplet States¹

  摘要：

  Peptides composed of alanine (Ala) and tryptophan (Trp), modified with the (nitro)pyrenesulfonyl chromophore (Pyr and NPyr) at the N-terminus have been examined by nanosecond laser flash photolysis. A common phototransient for Pyr-AlaOEt and Pyr-Ala-TrpOEt was observed that exhibited broad absorption at 410-550 nm and decay time constants in the range, tau(1/2) = 20-40 mu s. This species was assigned to the triplet excited state that is local to the pyrene chromophore ((3)Pyr). For the conjugates having a stronger electron acceptor group at the N-terminus, NPyr-Ala-TrpOEt and NPyr-Ala-Ala-TrpOEt, the local triplet was replaced with a phototransient whose principal feature is a sharp band at 440 nm (assigned to the NPyr(-.) radical anion). The radical ion transients for the NPyr peptide derivatives were assigned to intermediates that result from the intramolecular electron transfer quenching of NP excited species by pendant groups (i.e., the indole ring of tryptophan). The lifetimes observed for the radical ion transients associated with the NPyr series were relatively long (extending to ca. 400 ns) and depended in an interesting way on the structure of the peptide linkage. A mechanism of electron transfer in the singlet manifold and recombination yielding a local Pyr triplet state is important for the Pyr series.

  DOI：

  10.1021/jo981241g

文献信息

• Long-Lived Charge-Separated Species Observed on Flash Photolysis of Peptide Conjugates. Interplay of Local and Radical Ion Pair Triplet States¹
  作者：Guilford Jones、Lily N. Lu

  DOI：10.1021/jo981241g

  日期：1998.11.1

  Peptides composed of alanine (Ala) and tryptophan (Trp), modified with the (nitro)pyrenesulfonyl chromophore (Pyr and NPyr) at the N-terminus have been examined by nanosecond laser flash photolysis. A common phototransient for Pyr-AlaOEt and Pyr-Ala-TrpOEt was observed that exhibited broad absorption at 410-550 nm and decay time constants in the range, tau(1/2) = 20-40 mu s. This species was assigned to the triplet excited state that is local to the pyrene chromophore ((3)Pyr). For the conjugates having a stronger electron acceptor group at the N-terminus, NPyr-Ala-TrpOEt and NPyr-Ala-Ala-TrpOEt, the local triplet was replaced with a phototransient whose principal feature is a sharp band at 440 nm (assigned to the NPyr(-.) radical anion). The radical ion transients for the NPyr peptide derivatives were assigned to intermediates that result from the intramolecular electron transfer quenching of NP excited species by pendant groups (i.e., the indole ring of tryptophan). The lifetimes observed for the radical ion transients associated with the NPyr series were relatively long (extending to ca. 400 ns) and depended in an interesting way on the structure of the peptide linkage. A mechanism of electron transfer in the singlet manifold and recombination yielding a local Pyr triplet state is important for the Pyr series.