(2S,9S)-2-[(tert-Butoxycarbonyl)amino]-7-(carbobenzyloxy)-10-cyano-9-hydroxy-7-azadecanoic Acid tert-Butyl Ester | 214051-65-7

• 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,9S)-2-[(tert-Butoxycarbonyl)amino]-7-(carbobenzyloxy)-10-cyano-9-hydroxy-7-azadecanoic Acid tert-Butyl Ester
• 英文别名: tert-butyl (2S)-6-[[(2S)-3-cyano-2-hydroxypropyl]-phenylmethoxycarbonylamino]-2-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoate
• CAS: 214051-65-7
• 化学式: C₂₇H₄₁N₃O₇
• 分子量: 519.638
• InChiKey: YYEXDWRYHKNFEB-VXKWHMMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  37
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  138
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2S,9S)-2-[(tert-Butoxycarbonyl)amino]-7-(carbobenzyloxy)-10-cyano-9-hydroxy-7-azadecanoic Acid tert-Butyl Ester 在 platinum(IV) oxide 、 palladium on activated charcoal 氢气 、 potassium hydrogencarbonate 作用下， 以 乙醚 为溶剂， 反应 26.0h， 生成 (2S,9S)-11-[(Benzyloxycarbonyl)amino]-2-[(tert-butoxycarbonyl)amino]-9-hydroxy-7-(carbobenzyloxy)-7-azaundecanoic Acid tert-Butyl Ester
  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：

  N-Ε-苄氧羰基-L-赖氨酸叔丁酯盐酸盐 在 palladium on activated charcoal 盐酸 、 18-冠醚-6 、 氢气 、 碳酸氢钠 、 三乙胺 作用下， 以 乙醇 、 氯仿 、 乙腈 为溶剂， 反应 61.0h， 生成 (2S,9S)-2-[(tert-Butoxycarbonyl)amino]-7-(carbobenzyloxy)-10-cyano-9-hydroxy-7-azadecanoic Acid tert-Butyl Ester
  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

• 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.

  一种与Hypusine衍生物有关的试剂，可用于合成含有Hypusine的肽，以及一种改进的合成方法，该衍生物具有以下公式：其中：Q1和Q2可以相同或不同，并且是氨基保护基；Q3是一种与Q1和Q2正交的氨基保护基；Z是一种羟基保护基。
• US6248866B1
  申请人：——

  公开号：US6248866B1

  公开（公告）日：2001-06-19
• 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.