(2S,9R)-7-Benzyl-2-[(tert-butoxycarbonyl)amino]-10-cyano-9-hydroxy-7-azadecanoic Acid tert-Butyl Ester | 189280-04-4

• 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,9R)-7-Benzyl-2-[(tert-butoxycarbonyl)amino]-10-cyano-9-hydroxy-7-azadecanoic Acid tert-Butyl Ester
• 英文别名: tert-butyl (2S)-6-[benzyl-[(2R)-3-cyano-2-hydroxypropyl]amino]-2-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoate
• CAS: 189280-04-4
• 化学式: C₂₆H₄₁N₃O₅
• 分子量: 475.629
• InChiKey: WCMZYCHCIYOONO-YADHBBJMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  34
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2S,9R)-7-Benzyl-2-[(tert-butoxycarbonyl)amino]-10-cyano-9-hydroxy-7-azadecanoic Acid tert-Butyl Ester 在 platinum(IV) oxide 、 palladium on activated charcoal 氢气 、 sodium carbonate 、 N,N-二异丙基乙胺 作用下， 反应 6.0h， 生成 tert-butyl(2S,9R)-11-[(benzyloxycarbonyl)amino]-2-[(tert-butoxycarbonyl)amino]-9-hydroxy-7-(benzyloxycarbonyl)-7-azaundecanoate
  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：

  (S)-t-Boc-Lys(Bz)-O-t-Bu 在 18-冠醚-6 、 magnesium sulfate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 192.0h， 生成 (2S,9R)-7-Benzyl-2-[(tert-butoxycarbonyl)amino]-10-cyano-9-hydroxy-7-azadecanoic Acid tert-Butyl Ester
  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, Inc.

  公开号：US05973113A1

  公开（公告）日：1999-10-26

  A derivative of hypusine useful as a reagent for synthesizing peptides containing hypusine, as well as a method for synthesizing the same, the derivative having the formula: ##STR1## wherein: Q.sub.1 and Q.sub.2 may be the same or different and are amino protective groups; Q.sub.3 is an amino protective group which is orthogonal to Q.sub.1 and Q.sub.2 ; and Z is a hydroxy protective group.

  一种与Hypusine相关的衍生物，可用作合成含有Hypusine的肽的试剂，以及一种合成该衍生物的方法，该衍生物的化学式为：##STR1## 其中：Q.sub.1和Q.sub.2可以相同或不同，并且是氨基保护基；Q.sub.3是与Q.sub.1和Q.sub.2正交的氨基保护基；Z是羟基保护基。
• Synthetic hypusine peptides
  申请人：University of Florida Research Foundation, Inc.

  公开号：US06492489B1

  公开（公告）日：2002-12-10

  The invention relates to novel peptides synthesized according a method utilizing the hypusine reagent: wherein: Q1 Q2 and Q3 may be the same or different and are amino protective groups, provided that Q3 is orthogonal to Q1 and Q2; and Z is a hydroxy protective group, as well as improved methods of peptide synthesis wherein the above-described hypusine reagent is employed to prepare novel hypusine-containing peptides.

  本发明涉及一种利用hypusine试剂合成的新型肽，其中：Q1、Q2和Q3可以相同也可以不同，是氨基保护基，但要求Q3与Q1和Q2正交；Z是羟基保护基。同时，本发明还提供了改进的肽合成方法，其中上述hypusine试剂用于制备含有新型hypusine的肽。
• 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
• 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.