N-tert-butyloxycarbonyl-glycyl-glycine allyl ester | 236424-82-1

• 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: N-tert-butyloxycarbonyl-glycyl-glycine allyl ester
• 英文别名: Prop-2-enyl 2-[[2-[(2-methylpropan-2-yl)oxycarbonylamino]acetyl]amino]acetate；prop-2-enyl 2-[[2-[(2-methylpropan-2-yl)oxycarbonylamino]acetyl]amino]acetate
• CAS: 236424-82-1
• 化学式: C₁₂H₂₀N₂O₅
• 分子量: 272.301
• InChiKey: YOZYKMCOSHCUML-UHFFFAOYSA-N

物化性质

• 沸点：
  439.5±30.0 °C(Predicted)
• 密度：
  1.118±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-tert-butyloxycarbonyl-glycyl-glycine allyl ester 在 吗啉 、 四(三苯基膦)钯 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以68%的产率得到Boc-甘氨酰甘氨酸
  参考文献：
  名称：

  Synthesis of the palmitoylated and prenylated C-terminal lipopeptides of the human R- and N-Ras proteins

  摘要：

  For the study of biological phenomena influenced by the R- and N-Ras proteins, characteristic peptides which embody the correct lipid modifications of their parent proteins (palmitoyl thioesters, geranylgeranyl thioethers, and farnesyl thioethers), as well as analogues thereof, may serve as efficient tools. For the construction of such acid- and base labile peptide conjugates the allyl ester was developed as C-terminal protecting group. Allyl esters are cleaved selectively and in high yields from lipidated peptides by Pd(0)-mediated allyl transfer to accepting N- or C-nucleophiles like morpholine and N,N-dimethylbarbituric acid. This protecting group technique formed the key step in the synthesis of the characteristic S-palmitoylated and S-isoprenylated C-terminus of human R-Ras and human N-Ras proteins, as well as several analogues thereof. Deprotections are so mild that no undesired side reactions of the lipid conjugates are observed. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00251-x
• 作为产物：
  描述：

  BOC-甘氨酸 、 glycine allyl ester hydro-p-toluenesulfonate 在 1-羟基苯并三唑 、 达卡巴嗪 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以81%的产率得到N-tert-butyloxycarbonyl-glycyl-glycine allyl ester
  参考文献：
  名称：

  Synthesis of the palmitoylated and prenylated C-terminal lipopeptides of the human R- and N-Ras proteins

  摘要：

  For the study of biological phenomena influenced by the R- and N-Ras proteins, characteristic peptides which embody the correct lipid modifications of their parent proteins (palmitoyl thioesters, geranylgeranyl thioethers, and farnesyl thioethers), as well as analogues thereof, may serve as efficient tools. For the construction of such acid- and base labile peptide conjugates the allyl ester was developed as C-terminal protecting group. Allyl esters are cleaved selectively and in high yields from lipidated peptides by Pd(0)-mediated allyl transfer to accepting N- or C-nucleophiles like morpholine and N,N-dimethylbarbituric acid. This protecting group technique formed the key step in the synthesis of the characteristic S-palmitoylated and S-isoprenylated C-terminus of human R-Ras and human N-Ras proteins, as well as several analogues thereof. Deprotections are so mild that no undesired side reactions of the lipid conjugates are observed. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00251-x

文献信息

• [EN] SELECTIVE CYSTEINE PROTEASE INHIBITORS AND USES THEREOF<br/>[FR] INHIBITEURS SÉLECTIFS DE CYSTÉINE PROTÉASE ET LEURS UTILISATIONS
  申请人：NEW WORLD LAB INC

  公开号：WO2012140500A1

  公开（公告）日：2012-10-18

  The present invention relates to compounds of Formula I, II, IA-VA, IVA1-1VA5, 11IA1-IIIA5 and their pharmaceutical uses. Particular aspects of the invention relate to the use of those compounds for the selective inhibition of one or more cysteine proteases. Also described are methods where the compounds of Formula I, II, IA-VA, IVA1 -IVA5, IIIA1-IIIA5 are used in the prevention and/or treatment of various diseases and conditions in subjects, including cysteine protease-mediated diseases and/or caspase-mediated diseases such as sepsis, myocardial infarction, cancer, tissue atrophy, ischemia, ischemic stroke, spinal cord injury (SCI), traumatic brain injury (TBI) and neurodegenerative diseases such as multiple sclerosis (MS), ALS, Alzheimer's disease, Parkinson's disease, and Huntington's disease).
• Synthesis of the palmitoylated and prenylated C-terminal lipopeptides of the human R- and N-Ras proteins
  作者：T. Schmittberger、H. Waldmann

  DOI：10.1016/s0968-0896(98)00251-x

  日期：1999.5

  For the study of biological phenomena influenced by the R- and N-Ras proteins, characteristic peptides which embody the correct lipid modifications of their parent proteins (palmitoyl thioesters, geranylgeranyl thioethers, and farnesyl thioethers), as well as analogues thereof, may serve as efficient tools. For the construction of such acid- and base labile peptide conjugates the allyl ester was developed as C-terminal protecting group. Allyl esters are cleaved selectively and in high yields from lipidated peptides by Pd(0)-mediated allyl transfer to accepting N- or C-nucleophiles like morpholine and N,N-dimethylbarbituric acid. This protecting group technique formed the key step in the synthesis of the characteristic S-palmitoylated and S-isoprenylated C-terminus of human R-Ras and human N-Ras proteins, as well as several analogues thereof. Deprotections are so mild that no undesired side reactions of the lipid conjugates are observed. (C) 1999 Elsevier Science Ltd. All rights reserved.