tert-butyl(2S,9R)-11-[(benzyloxycarbonyl)amino]-2-[(tert-butoxycarbonyl)amino]-9-hydroxy-7-(benzyloxycarbonyl)-7-azaundecanoate | 189280-15-7

• 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: tert-butyl(2S,9R)-11-[(benzyloxycarbonyl)amino]-2-[(tert-butoxycarbonyl)amino]-9-hydroxy-7-(benzyloxycarbonyl)-7-azaundecanoate
• 英文别名: (2S,9R)-11-[(Benzyloxycarbonyl)amino]-2-[(tert-butoxycarbonyl)amino]-9-hydroxy-7-carbobenzyloxy-7-azaundecanoic Acid tert-Butyl Ester；tert-butyl (2S)-6-[[(2R)-2-hydroxy-4-(phenylmethoxycarbonylamino)butyl]-phenylmethoxycarbonylamino]-2-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoate
• CAS: 189280-15-7
• 化学式: C₃₅H₅₁N₃O₉
• 分子量: 657.805
• InChiKey: OXOOFDJOOGWUIV-WDYNHAJCSA-N

物化性质

• 沸点：
  766.9±60.0 °C(Predicted)
• 密度：
  1.160±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  47
• 可旋转键数：
  22
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  153
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  tert-butyl(2S,9R)-11-[(benzyloxycarbonyl)amino]-2-[(tert-butoxycarbonyl)amino]-9-hydroxy-7-(benzyloxycarbonyl)-7-azaundecanoate 在 哌啶 、 三乙基硅烷 、 三异丙基硅烷 、 五甲基苯 、 氢溴酸 、 sodium carbonate 、 溶剂黄146 、 三氟乙酸 、 苯酚 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 44.0h， 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：

  (S)-t-Boc-Lys(Bz)-O-t-Bu 在 platinum(IV) oxide 、 palladium on activated charcoal 18-冠醚-6 、 氢气 、 sodium carbonate 、 magnesium sulfate 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 198.0h， 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

文献信息

• (R)- and (S)-N-(Benzyloxycarbonyl)-3,4-epoxybutylamine. New 4-amino-2-hydroxybutyl synthons for the synthesis of hypusine reagents and (R)-6- and (S)-7-hydroxyspermidine
  作者：Raymond J. Bergeron、Jörg Bussenius、Ralf Müller、Bruce H. McCosar、James S. McManis

  DOI：10.1016/s0957-4166(99)00474-7

  日期：1999.11

  The synthesis and application of the chiral reagents (R)- and (S)-N-(benzyloxycarbonyl)-3,4-epoxybutylamine is described for the first time. These 4-amino-2-hydroxybutyl synthons are successfully employed in the assembly of two hydroxylated triamines, (R)-6- and (S)-7-hydroxyspermidine, and a previously described hypusine reagent, (2S,9R)-11-[(benzyloxycarbonyl)amino]-7-(benzyloxycarbonyl)-2-[(9-f

  首次描述了手性试剂（R）-和（S）-N-（苄氧羰基）-3,4-环氧丁胺的合成和应用。这些4-氨基-2-羟基丁基合成子已成功用于组装两个羟基化三胺（R）-6-和（S）-7-羟基亚精胺，以及先前描述的Hysupsine试剂（2 S，9 R）- 11-[（苄氧基羰基）氨基] -7-（苄氧基羰基）-2-[（9-芴基甲氧基羰基）氨基] -9-（四氢吡喃-2-基氧基）-7-氮杂十一烷酸，用于溶液和固相肽合成。
• 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。
• 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