deoxyhypusine | 82543-85-9

• 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: deoxyhypusine
• 英文别名: (2S)-2-amino-6-(4-aminobutylamino)hexanoic acid
• CAS: 82543-85-9
• 化学式: C₁₀H₂₃N₃O₂
• 分子量: 217.312
• InChiKey: PGPFBXMCOQNMJO-VIFPVBQESA-N

物化性质

• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  -2.8
• 重原子数：
  15
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  101
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  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

文献信息

• 一种氨基酸-胺缀合物及其制备方法和应用
  申请人：河南大学

  公开号：CN103833623B

  公开（公告）日：2016-07-06

  本发明属于药物化学领域，具体涉及一种氨基酸-胺缀合物及其制备方法和应用。该氨基酸-胺缀合物具有如下通式：。本发明把氨基酸和胺结合在一起，可以改善胺类化合物的水溶性、生物性能和药物靶向性，实现抗肿瘤的靶向作用。
• Piperidone derivatives and medical uses thereof
  申请人：Heinrich-Pette-Institut

  公开号：EP2036556A1

  公开（公告）日：2009-03-18

  The present invention relates to compositions comprising 4-Oxo-piperidine-carboxylates and derivatives thereof, for example derivatives substituted with phenyl, nitrophenyl or benzyl groups. It also teaches the medical use of these and related compounds for treatment of retroviral diseases, in particular, HIV and HTLV, proliferative diseases, in particular CML and Trypanosomiasis.

  本发明涉及包含4-氧代哌啶羧酸酯及其衍生物的组合物，例如用苯基、硝基苯基或苄基取代的衍生物。它还教导了这些相关化合物的医药用途，用于治疗逆转录病毒性疾病，特别是HIV和HTLV，增殖性疾病，特别是慢性髓细胞白血病和锥虫病。
• Pyrimidinium-guanidiniminoethylphenyl-guanidinoalkyl-amines and guanidiniminoethylphenyl-guanidinoalkylamines as pharmaceutically active new substances
  申请人：Mondobiotech SA

  公开号：EP1413300A1

  公开（公告）日：2004-04-28

  The present invention relates to new compositions and methods for use as pharmaceutically active agents, especially for prophylaxis and prevention in virally caused infections and diseases, tumor necrosis factor alpha (TNFα)-related inflammatory conditions and diseases, graft rejection after organ or tissue transplantations, and cancer. The innovative compounds are inhibitors of Hypusine formation and nuclear transport of distinct RNAs from nucleus to cytoplasm.

  本发明涉及新的组合物和方法，用作药物活性剂，特别是用于预防和治疗病毒引起的感染和疾病、肿瘤坏死因子α（TNFα）相关的炎症性疾病、器官或组织移植后的移植排斥反应以及癌症。这些创新化合物是Hypusine形成和将特定RNA从细胞核转运到细胞质的抑制剂。
• Determination of Covalently Bound Hypusine and Deoxyhypusine to Protein Using Submilligram of Protein Samples by HPLC.
  作者：Takanobu BEPPU、Akira SHIRAHATA、Keijiro SAMEJIMA

  DOI：10.1248/bpb.19.1

  日期：——

  A sensitive and reliable method for the determination of hypusine and deoxyhypusine in eIF-5A protein, an initiation factor of protein synthesis, was developed. An advantage of this method is the use of Nε-(5-aminopentyl) lysine, an analogue of deoxyhypusine, as an internal standard. The application made it possible to determine hypusine in less than a mg of protein samples from cultured HTC cells and rat organs. After acid hydrolysis of protein samples to which had been added the internal standard, the hydrolysates were fractionated by carboxymethyl cellulose column chromatography. Also, diamine fractions containing a few pmol of hypusine and deoxyhypusine were successfully analyzed by a reversed phase HPLC with a fluorescence detection of o-phthalaldehyde. The method was applied for the determination of hypusine and deoxyhypusine in drug-treated HTC cells and normal rat organs. The results from HTC cells were discussed based on the known effects of each drug on hypusine biosynthesis.

  本研究建立了一种灵敏可靠的方法，用于测定蛋白质合成起始因子 eIF-5A 蛋白中的次碱和脱氧次碱。该方法的优点是使用 Nε-(5-氨基戊基)赖氨酸（脱氧羽扇豆碱的类似物）作为内标物。这一应用使得从培养的 HTC 细胞和大鼠器官中检测不到一毫克蛋白质样品中的次碱成为可能。在对添加了内标物的蛋白质样品进行酸水解后，水解物通过羧甲基纤维素柱色谱法进行分馏。此外，通过反相高效液相色谱法和邻苯二甲醛荧光检测法，成功地分析了含有几pmol次碱和脱氧次碱的二胺馏分。该方法被用于测定药物处理的 HTC 细胞和正常大鼠器官中的次碱和脱氧次碱。根据每种药物对次碱生物合成的已知影响，对来自 HTC 细胞的结果进行了讨论。
• Abrogating HIV-1 Infection via Drug-Induced Reactivation of Apoptosis
  申请人：Mathews Michael B.

  公开号：US20120225093A1

  公开（公告）日：2012-09-06

  The present invention relates to compositions and methods of treating, inhibiting, or controlling HIV infection.

  本发明涉及用于治疗、抑制或控制HIV感染的组合物和方法。