[(2S,3R)-2-((R)-2-Benzyloxycarbonylamino-3-benzyloxycarbonylsulfanyl-propionylamino)-3-tert-butoxy-butyrylamino]-acetic acid | 189280-47-5

• 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: [(2S,3R)-2-((R)-2-Benzyloxycarbonylamino-3-benzyloxycarbonylsulfanyl-propionylamino)-3-tert-butoxy-butyrylamino]-acetic acid
• 英文别名: Cbz-Cys(Cbz)(Cbz)-Thr(tBu)-Gly-OH；2-[[(2S,3R)-3-[(2-methylpropan-2-yl)oxy]-2-[[(2R)-2-(phenylmethoxycarbonylamino)-3-phenylmethoxycarbonylsulfanylpropanoyl]amino]butanoyl]amino]acetic acid
• CAS: 189280-47-5
• 化学式: C₂₉H₃₇N₃O₉S
• 分子量: 603.693
• InChiKey: JLNBAWPVRUOGOQ-UCFCWBNQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  42
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  195
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  [(2S,3R)-2-((R)-2-Benzyloxycarbonylamino-3-benzyloxycarbonylsulfanyl-propionylamino)-3-tert-butoxy-butyrylamino]-acetic acid 、 4-[(S)-2-((S)-2-Amino-6-{benzyloxycarbonyl-[(R)-4-benzyloxycarbonylamino-2-(tetrahydro-pyran-2-yloxy)-butyl]-amino}-hexanoylamino)-2-(tert-butoxycarbonylmethyl-carbamoyl)-ethyl]-imidazole-1-carboxylic acid tert-butyl ester 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 生成 CBZ-Cys(CBZ)-Thr(O-t-Bu)-Gly-Hpu(N7,N12-di-CBZ,O9-THP)-His(BOC)-Gly-O-tBu
  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：

  N,S-二-Z-L-半胱氨酸 在 sodium carbonate 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 二乙胺 、 N,N-二异丙基乙胺 、 柠檬酸 作用下， 反应 0.08h， 生成 [(2S,3R)-2-((R)-2-Benzyloxycarbonylamino-3-benzyloxycarbonylsulfanyl-propionylamino)-3-tert-butoxy-butyrylamino]-acetic acid
  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.