tert-butyl (2S)-2-[[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-6-[[(2R)-2-(oxan-2-yloxy)-4-(phenylmethoxycarbonylamino)butyl]-phenylmethoxycarbonylamino]hexanoyl]amino]-3-methylbutanoate | 214051-77-1

• 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: tert-butyl (2S)-2-[[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-6-[[(2R)-2-(oxan-2-yloxy)-4-(phenylmethoxycarbonylamino)butyl]-phenylmethoxycarbonylamino]hexanoyl]amino]-3-methylbutanoate
• CAS: 214051-77-1
• 化学式: C₅₅H₇₀N₄O₁₁
• 分子量: 963.181
• InChiKey: RAAROHZRSYRJQU-XYNWJIDXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  70
• 可旋转键数：
  28
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  180
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S)-2-[[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-6-[[(2R)-2-(oxan-2-yloxy)-4-(phenylmethoxycarbonylamino)butyl]-phenylmethoxycarbonylamino]hexanoyl]amino]-3-methylbutanoate 在 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 以89%的产率得到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：

  L-缬氨酸叔丁酯盐酸盐 、 (2S,9R)-11-[(Benzyloxycarbonyl)amino]-7-(carbobenzyloxy)-2-[(9-fluorenylmethoxycarbonyl)amino]-9-(tetrahydropyran-2-yloxy)-7-azaundecanoic Acid 在 (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 21.0h， 以83%的产率得到tert-butyl (2S)-2-[[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-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

文献信息

• Synthesis of Reagents for the Construction of Hypusine and Deoxyhypusine Peptides and Their Application as Peptidic Antigens
  作者：Raymond J. Bergeron、William R. Weimar、Ralf Müller、Curt O. Zimmerman、Bruce H. McCosar、Hua Yao、Richard E. Smith

  DOI：10.1021/jm980389p

  日期：1998.9.1

  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.