[(S)-2-Benzyloxycarbonylamino-3-(1H-imidazol-4-yl)-propionylamino]-acetic acid tert-butyl ester | 189280-51-1

• 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: [(S)-2-Benzyloxycarbonylamino-3-(1H-imidazol-4-yl)-propionylamino]-acetic acid tert-butyl ester
• 英文别名: tert-butyl 2-[[(2S)-3-(1H-imidazol-5-yl)-2-(phenylmethoxycarbonylamino)propanoyl]amino]acetate
• CAS: 189280-51-1
• 化学式: C₂₀H₂₆N₄O₅
• 分子量: 402.45
• InChiKey: KBIYWTGOMUDKRE-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  122
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(S)-2-Benzyloxycarbonylamino-3-(1H-imidazol-4-yl)-propionylamino]-acetic acid tert-butyl ester 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 2.5h， 生成 4-[(S)-2-Amino-2-(tert-butoxycarbonylmethyl-carbamoyl)-ethyl]-imidazole-1-carboxylic acid tert-butyl ester; hydrochloride
  参考文献：
  名称：

  Development of a Hypusine Reagent for Peptide Synthesis

  摘要：

  The synthesis of a reagent that enables the incorporation of the unusual amino acid (2S,9R)hypusine (Hpu) into peptide sequences is described. The reagent, (2S,SR)-11-[(benzyloxycarbonyl)amino]-7-(carbobenzyloxy)-2- [(9-fluorenylmethoxycarbonyl)amino]-9-(tetrahydropyran-2-yloxy)- 7-azaundecanoic acid, is utilized in the synthesis of a hexapeptide containing the primary pentapeptide sequence of the eukaryotic initiation factor eIF-5A, L-Cys-L-Thr-Gly-Hpu-L-His-Gly. The reagent is shown to be effective for both solution phase and Merrifield resin synthesis.

  DOI：

  10.1021/jo970119z
• 作为产物：
  描述：

  甘氨酸叔丁酯盐酸盐 、 N-Cbz-L-组氨酸 在 二苯基磷酸 、 三乙胺 作用下， 生成 [(S)-2-Benzyloxycarbonylamino-3-(1H-imidazol-4-yl)-propionylamino]-acetic acid tert-butyl ester
  参考文献：
  名称：

  Development of a Hypusine Reagent for Peptide Synthesis

  摘要：

  The synthesis of a reagent that enables the incorporation of the unusual amino acid (2S,9R)hypusine (Hpu) into peptide sequences is described. The reagent, (2S,SR)-11-[(benzyloxycarbonyl)amino]-7-(carbobenzyloxy)-2- [(9-fluorenylmethoxycarbonyl)amino]-9-(tetrahydropyran-2-yloxy)- 7-azaundecanoic acid, is utilized in the synthesis of a hexapeptide containing the primary pentapeptide sequence of the eukaryotic initiation factor eIF-5A, L-Cys-L-Thr-Gly-Hpu-L-His-Gly. The reagent is shown to be effective for both solution phase and Merrifield resin synthesis.

  DOI：

  10.1021/jo970119z

文献信息

• Development of a Hypusine Reagent for Peptide Synthesis
  作者：Raymond J. Bergeron、Christian Ludin、Ralf Müller、Richard E. Smith、Phanstiel

  DOI：10.1021/jo970119z

  日期：1997.5.1

  The synthesis of a reagent that enables the incorporation of the unusual amino acid (2S,9R)hypusine (Hpu) into peptide sequences is described. The reagent, (2S,SR)-11-[(benzyloxycarbonyl)amino]-7-(carbobenzyloxy)-2- [(9-fluorenylmethoxycarbonyl)amino]-9-(tetrahydropyran-2-yloxy)- 7-azaundecanoic acid, is utilized in the synthesis of a hexapeptide containing the primary pentapeptide sequence of the eukaryotic initiation factor eIF-5A, L-Cys-L-Thr-Gly-Hpu-L-His-Gly. The reagent is shown to be effective for both solution phase and Merrifield resin synthesis.