N-[N-[(1,3-二氢-1,3-二氧代-2H-异吲哚-2-基)乙酰基]甘氨酰]甘氨酸 | 93923-88-7

• 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
• 中文名称: N-[N-[(1,3-二氢-1,3-二氧代-2H-异吲哚-2-基)乙酰基]甘氨酰]甘氨酸
• 英文名称: N-[N-(N,N-phthaloyl-glycyl)-glycyl]-glycine
• 英文别名: N-[N-(N,N-Phthaloyl-glycyl)-glycyl]-glycin；N,N-Phthaloyl-glycyl=>glycyl=>-glycin；N-{N-[(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)acetyl]glycyl}glycine；N-Phthaloyl-Gly-Gly-Gly；Phthaloyl-gly-gly-gly；N-(N-((1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)acetyl)glycyl)glycine；2-[[2-[[2-(1,3-dioxoisoindol-2-yl)acetyl]amino]acetyl]amino]acetic acid
• CAS: 93923-88-7
• 化学式: C₁₄H₁₃N₃O₆
• 分子量: 319.274
• InChiKey: QPJQIQMWOUOCOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  133
• 氢给体数：
  3
• 氢受体数：
  6

安全信息

• 海关编码：
  2925190090

反应信息

• 作为反应物：
  描述：

  N-[N-[(1,3-二氢-1,3-二氧代-2H-异吲哚-2-基)乙酰基]甘氨酰]甘氨酸 在 四丁基氢氧化铵 作用下， 以 水 、 乙腈 为溶剂， 反应 10.0h， 以20%的产率得到4b-Hydroxy-5,6,8,9-tetrahydro-4bH-6,9,11a-triaza-cyclonona[a]indene-7,10,12-trione
  参考文献：
  名称：

  A Synthetic Strategy for the Preparation of Cyclic Peptide Mimetics Based on SET-Promoted Photocyclization Processes

  摘要：

  A novel method for the synthesis of cyclic peptide analogues has been developed. The general approach relies on the use of SET-promoted photocyclization reactions of peptides that contain N-terminal phthalimides as light absorbing electron acceptor moieties and C-terminal alpha-amidosilane or alpha-amidocarboxylate centers. Prototypical substrates are prepared by coupling preformed peptides with the acid chloride of N-phthalimidoglycine. Irradiation of these substrates results in the generation of cyclic peptide analogues in modest to good yields. The chemical efficiencies of these processes are not significantly affected by (1) the lengths of the peptide chains separating the phthalimide and alpha-amidosilane or alpha-amidocarboxylate centers and (2) the nature of the penultimate cation radical a-heterolytic fragmentation process (i.e., desilylation vs decarboxylation). An evaluation of the effects of N-alkyl substitution on the amide residues in the peptide chain showed that N-alkyl substitution does not have a major impact on the efficiencies of the photocyclization reactions but that it profoundly increases the stability of the cyclic peptide.

  DOI：

  10.1021/ja030297b
• 作为产物：
  描述：

  双甘肽 、 N-邻苯二甲酰甘氨酰氯 在 magnesium oxide 作用下， 以 水 、 1,4-二氧六环 为溶剂， 反应 6.0h， 以87%的产率得到N-[N-[(1,3-二氢-1,3-二氧代-2H-异吲哚-2-基)乙酰基]甘氨酰]甘氨酸
  参考文献：
  名称：

  A Synthetic Strategy for the Preparation of Cyclic Peptide Mimetics Based on SET-Promoted Photocyclization Processes

  摘要：

  A novel method for the synthesis of cyclic peptide analogues has been developed. The general approach relies on the use of SET-promoted photocyclization reactions of peptides that contain N-terminal phthalimides as light absorbing electron acceptor moieties and C-terminal alpha-amidosilane or alpha-amidocarboxylate centers. Prototypical substrates are prepared by coupling preformed peptides with the acid chloride of N-phthalimidoglycine. Irradiation of these substrates results in the generation of cyclic peptide analogues in modest to good yields. The chemical efficiencies of these processes are not significantly affected by (1) the lengths of the peptide chains separating the phthalimide and alpha-amidosilane or alpha-amidocarboxylate centers and (2) the nature of the penultimate cation radical a-heterolytic fragmentation process (i.e., desilylation vs decarboxylation). An evaluation of the effects of N-alkyl substitution on the amide residues in the peptide chain showed that N-alkyl substitution does not have a major impact on the efficiencies of the photocyclization reactions but that it profoundly increases the stability of the cyclic peptide.

  DOI：

  10.1021/ja030297b

文献信息

• Preparation of peptides
  申请人：EMERSON OLIVER H

  公开号：US02498665A1

  公开（公告）日：1950-02-28
• Yamashita; Yashiro, Nippon Nogeikagaku Kaishi, 1954, vol. 28, p. 674
  作者：Yamashita、Yashiro

  DOI：——

  日期：——
• Utzino, Journal of Biochemistry, vol. 9, p. 458
  作者：Utzino

  DOI：——

  日期：——
• A Synthetic Strategy for the Preparation of Cyclic Peptide Mimetics Based on SET-Promoted Photocyclization Processes
  作者：Ung Chan Yoon、Ying Xue Jin、Sun Wha Oh、Chan Hyo Park、Jong Hoon Park、Charles F. Campana、Xiaolu Cai、Eileen N. Duesler、Patrick S. Mariano

  DOI：10.1021/ja030297b

  日期：2003.9.1

  A novel method for the synthesis of cyclic peptide analogues has been developed. The general approach relies on the use of SET-promoted photocyclization reactions of peptides that contain N-terminal phthalimides as light absorbing electron acceptor moieties and C-terminal alpha-amidosilane or alpha-amidocarboxylate centers. Prototypical substrates are prepared by coupling preformed peptides with the acid chloride of N-phthalimidoglycine. Irradiation of these substrates results in the generation of cyclic peptide analogues in modest to good yields. The chemical efficiencies of these processes are not significantly affected by (1) the lengths of the peptide chains separating the phthalimide and alpha-amidosilane or alpha-amidocarboxylate centers and (2) the nature of the penultimate cation radical a-heterolytic fragmentation process (i.e., desilylation vs decarboxylation). An evaluation of the effects of N-alkyl substitution on the amide residues in the peptide chain showed that N-alkyl substitution does not have a major impact on the efficiencies of the photocyclization reactions but that it profoundly increases the stability of the cyclic peptide.