11-[(Benzyloxycarbonyl)amino]-7-(carbobenzyloxy)-2(S)-[(9-fluorenylmethoxycarbonyl)amino]-7-azaundecanoic Acid | 214051-93-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 11-[(Benzyloxycarbonyl)amino]-7-(carbobenzyloxy)-2(S)-[(9-fluorenylmethoxycarbonyl)amino]-7-azaundecanoic Acid
• 英文别名: (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-6-[phenylmethoxycarbonyl-[4-(phenylmethoxycarbonylamino)butyl]amino]hexanoic acid
• CAS: 214051-93-1
• 化学式: C₄₁H₄₅N₃O₈
• 分子量: 707.824
• InChiKey: XYYFNRZWAVUACK-QNGWXLTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  52
• 可旋转键数：
  21
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  144
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  11-[(Benzyloxycarbonyl)amino]-7-(carbobenzyloxy)-2(S)-[(9-fluorenylmethoxycarbonyl)amino]-7-azaundecanoic Acid 在 哌啶 、 三异丙基硅烷 、 五甲基苯 、 氢溴酸 、 溶剂黄146 、 苯酚 作用下， 生成 deoxyhypusine
  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：

  苯甲氧羰酰琥珀酰亚胺 在 三乙基硅烷 、 sodium carbonate 、 potassium hydrogencarbonate 、 三氟乙酸 作用下， 以 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 11-[(Benzyloxycarbonyl)amino]-7-(carbobenzyloxy)-2(S)-[(9-fluorenylmethoxycarbonyl)amino]-7-azaundecanoic Acid
  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

• Deoxyhypusine reagent and peptides
  申请人：University of Florida Research Foundation, Inc.

  公开号：US06258931B1

  公开（公告）日：2001-07-10

  The invention relates to a method and reagent for the synthesis of peptides containing deoxyhypusine, the reagent having the formula: wherein: Q1 and Q2 may be the same or different and are amino protective groups, and Q3 is an amino protective group which is orthogonal to Q1 and Q2. The invention also relates to peptides of formula S-deoxyHpu-T  (2) that may be synthesized using the reagent of the invention, wherein deoxyHpu is the deoxyhypusine residue, S and T are each independently peptide residues from zero to 12 amino acids in length.

  本发明涉及一种合成含有脱氧低聚嘌呤的肽的方法和试剂，所述试剂具有以下式子：其中：Q1和Q2可以相同也可以不同，是氨基保护基，Q3是一种与Q1和Q2正交的氨基保护基。本发明还涉及利用本发明的试剂合成的式子为S-脱氧Hpu-T（2）的肽，其中，脱氧Hpu是脱氧低聚嘌呤残基，S和T分别是长度为零到12个氨基酸的肽残基。
• DEOXYHYPUSINE REAGENT AND PEPTIDES
  申请人：UNIVERSITY OF FLORIDA RESEARCH FOUNDATION, INC.

  公开号：EP1032585B1

  公开（公告）日：2004-11-24
• US6258931B1
  申请人：——

  公开号：US6258931B1

  公开（公告）日：2001-07-10
• 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.