(2S,9R)-11-[(Benzyloxycarbonyl)amino]-7-(carbobenzyloxy)-2-[(9-fluorenylmethoxycarbonyl)amino]-9-(tetrahydropyran-2-yloxy)-7-azaundecanoic Acid | 189280-27-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (2S,9R)-11-[(Benzyloxycarbonyl)amino]-7-(carbobenzyloxy)-2-[(9-fluorenylmethoxycarbonyl)amino]-9-(tetrahydropyran-2-yloxy)-7-azaundecanoic Acid
• 英文别名: (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-6-[[(2R)-2-(oxan-2-yloxy)-4-(phenylmethoxycarbonylamino)butyl]-phenylmethoxycarbonylamino]hexanoic acid
• CAS: 189280-27-1
• 化学式: C₄₆H₅₃N₃O₁₀
• 分子量: 807.941
• InChiKey: TVNQDYKYMBPCMV-RGKZAMRZSA-N

物化性质

• 沸点：
  968.8±65.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  59
• 可旋转键数：
  23
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  162
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (2S,9R)-11-[(Benzyloxycarbonyl)amino]-7-(carbobenzyloxy)-2-[(9-fluorenylmethoxycarbonyl)amino]-9-(tetrahydropyran-2-yloxy)-7-azaundecanoic Acid 在 哌啶 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 25.5h， 生成 tert-butyl (2S)-2-[[(2S)-2-amino-6-[[(2R)-2-(oxan-2-yloxy)-4-(phenylmethoxycarbonylamino)butyl]-phenylmethoxycarbonylamino]hexanoyl]amino]-3-methylbutanoate
  参考文献：
  名称：

  Synthesis of Reagents for the Construction of Hypusine and Deoxyhypusine Peptides and Their Application as Peptidic Antigens

  摘要：

  Two new synthetic methods which allow access to (2S)-deoxyhypusine, natural (2S,9R)hypusine, (2S,SS)-hypusine, and deoxyhypusine- and hypusine-containing peptides are described. The methods involve both the construction of a deoxyhypusine reagent in which the alpha-nitrogen protecting group is orthogonal to the N-7 and N-12 protecting groups and an alternate synthesis of our previous hypusine reagent, a synthesis which provides for better stereochemical control at C-9. Synthetic hypusine and deoxyhypusine can be generated from these reagents. The hypusine-containing hexapeptide (Cys-Thr-Gly-Hpu-His-Gly) is conjugated to ovalbumin (OVA), keyhole limpet hemocyanin (KLH), and a bis-maleimide; KLH conjugates are also made with the deoxyhypusine- and lysine-containing hexapeptides. Monoclonal antibodies are generated to the hypusine-containing hexapeptide-OVA conjugate in mice. These are isolated and screened against the hypusine-containing hexapeptide-KLH and hypusine-containing hexapeptide-bis-maleimide conjugates, as well as against the deoxyhypusine-containing and lysine-containing hexapeptide-KLH conjugates. These antibodies may be useful in localizing intracellular hypusine-containing peptides as well as peptides containing hypusine analogues.

  DOI：

  10.1021/jm980389p
• 作为产物：
  描述：

  9-芴甲基-N-琥珀酰亚胺基碳酸酯 、 (2S,9R)-2-Amino-11-[(Benzyloxycarbonyl)amino]-7-(carbobenzyloxy)-9-(tetrahydropyran-2-yloxy)-7-azaundecanoic Acid 在 sodium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以83%的产率得到(2S,9R)-11-[(Benzyloxycarbonyl)amino]-7-(carbobenzyloxy)-2-[(9-fluorenylmethoxycarbonyl)amino]-9-(tetrahydropyran-2-yloxy)-7-azaundecanoic 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

• Hypusine reagent for peptide synthesis
  申请人：University of Florida Research Foundation, Incorporated

  公开号：US06248866B1

  公开（公告）日：2001-06-19

  A derivative of hypusine useful as a reagent for synthesizing peptides containing hypusine, as well as an improved method for synthesizing the same, the derivative having the formula: wherein: Q1 and Q2 may be the same or different and are amino protective groups; Q3 is an amino protective group which is orthogonal to Q1 and Q2; and Z is a hydroxy protective group.

  一种hypusine衍生物，可用作合成含有hypusine肽的试剂，并提供了一种改进的合成方法，该衍生物的化学式为：其中：Q1和Q2可以相同或不同，是氨基保护基；Q3是与Q1和Q2正交的氨基保护基；Z是羟基保护基。
• 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.
• HYPUSINE REAGENT FOR PEPTIDE SYNTHESIS
  申请人：UNIVERSITY OF FLORIDA RESEARCH FOUNDATION, INC.

  公开号：EP1032411B1

  公开（公告）日：2005-04-20
• US6248866B1
  申请人：——

  公开号：US6248866B1

  公开（公告）日：2001-06-19
• US6492491B1
  申请人：——

  公开号：US6492491B1

  公开（公告）日：2002-12-10