3(R)-[(tert-butyloxycarbonyl)amino]-2-oxo-1-azepineacetic acid | 78444-83-4

• 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: 3(R)-[(tert-butyloxycarbonyl)amino]-2-oxo-1-azepineacetic acid
• 英文别名: 3(R)-3-(Boc-amino)-2-oxo-1-piperidine-acetic acid；t-butoxy-(3R)-3-amino-1-carboxymethyl-caprolactam；(R)-3-(Boc-amino)-2-oxo-1-azepine-acetic acid, AldrichCPR；2-[(3R)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-2-oxoazepan-1-yl]acetic acid
• CAS: 78444-83-4
• 化学式: C₁₃H₂₂N₂O₅
• 分子量: 286.328
• InChiKey: JABSORAZQPYNMZ-SECBINFHSA-N

物化性质

• 沸点：
  507.3±50.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  95.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3(R)-[(tert-butyloxycarbonyl)amino]-2-oxo-1-azepineacetic acid 在 三氟乙酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 1.0h， 以100%的产率得到3(R)-3-amino-2-oxo-1-piperidine-acetic acid
  参考文献：
  名称：

  Structure–activity relationships of a peptide inhibitor of the human FcRn:human IgG interaction

  摘要：

  A family of five peptides was previously discovered by phage display techniques that binds to the human neonatal Fc receptor (FcRn) and inhibits the human IgG: human FcRn protein-protein interaction [Proc. Nat. Acad. Sci. U. S. A. 2008, 105, 2337-2342]. The consensus peptide motif consists of the sequence GHFGGXY where X is preferably a hydrophobic amino acid, and also includes a disul. de bridge enclosing 11-amino acids in varying positions about the consensus sequence. We describe herein the structure activity relationships of one of the five peptides in binding to FcRn using surface plasmon resonance and IgG: FcRn competition ELISA assays. Modi. cations of the peptide length, cyclization, and the incorporation of amino acid substitutions and dipeptide mimetics were studied. The most potent analogs exhibited a 50-to 100-fold improvement of in vitro activity over that of the phage-identified peptide sequence. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.05.004
• 作为产物：
  描述：

  N-(叔丁氧羰基)-D-赖氨酸 在 palladium on activated charcoal 氢气 、 sodium hydride 、 碳酸氢钠 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.25h， 生成 3(R)-[(tert-butyloxycarbonyl)amino]-2-oxo-1-azepineacetic acid
  参考文献：
  名称：

  缓激肽B（2）受体激动剂的合成和表征包含约束的二肽模拟物。

  摘要：

  先前我们已经证明了D-Tic-Oic二肽被（3S）-[氨基] -5-（羰基甲基）-2,3-二氢-1，5-苯并噻唑啉-4（5H）-一个（D -BT）缓激肽B（2）受体拮抗剂HOE 140中的部分导致了完全有效和选择性的缓激肽B（2）受体激动剂（H-DArg-Arg-Pro-Hyp-Gly-Thi-Ser-D-BT- Arg-OH，JMV1116）对人受体具有高亲和力（K（i）0.7 nM）。在本研究中，我们研究了各种约束的二肽模拟物替代D-Tic-Oic部分的影响。测试了所得化合物对克隆的人B（2）受体的结合亲和力以及与缓激肽诱导的孤立人脐静脉收缩的功能相互作用。后来，我们设计了新型缓激肽B（2）受体激动剂，它们可能对内肽酶的酶促裂解具有抗性，并且可能代表了有趣的新药理学工具。为了增加化合物JMV1116的效力，其N端部分和D-BT部分都被修饰。D-精氨酸残基被L-赖氨酸残基取代导致更有效的

  DOI：

  10.1021/jm9901531

文献信息

• WO2007/101347
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis and Characterization of Bradykinin B₂ Receptor Agonists Containing Constrained Dipeptide Mimics
  作者：Muriel Amblard、Isabelle Daffix、Gilbert Bergé、Monique Calmès、Pierre Dodey、Didier Pruneau、Jean-Luc Paquet、Jean-Michel Luccarini、Pierre Bélichard、Jean Martinez

  DOI：10.1021/jm9901531

  日期：1999.10.1

  study, we have investigated the effects of replacement of the D-Tic-Oic moiety by various constrained dipeptide mimetics. The resulting compounds were tested for their binding affinity toward the cloned human B(2) receptor and for their functional interaction with the bradykinin-induced contraction of isolated human umbilical vein. Subsequently, we have designed novel bradykinin B(2) receptor agonists

  先前我们已经证明了D-Tic-Oic二肽被（3S）-[氨基] -5-（羰基甲基）-2,3-二氢-1，5-苯并噻唑啉-4（5H）-一个（D -BT）缓激肽B（2）受体拮抗剂HOE 140中的部分导致了完全有效和选择性的缓激肽B（2）受体激动剂（H-DArg-Arg-Pro-Hyp-Gly-Thi-Ser-D-BT- Arg-OH，JMV1116）对人受体具有高亲和力（K（i）0.7 nM）。在本研究中，我们研究了各种约束的二肽模拟物替代D-Tic-Oic部分的影响。测试了所得化合物对克隆的人B（2）受体的结合亲和力以及与缓激肽诱导的孤立人脐静脉收缩的功能相互作用。后来，我们设计了新型缓激肽B（2）受体激动剂，它们可能对内肽酶的酶促裂解具有抗性，并且可能代表了有趣的新药理学工具。为了增加化合物JMV1116的效力，其N端部分和D-BT部分都被修饰。D-精氨酸残基被L-赖氨酸残基取代导致更有效的
• Structure–activity relationships of a peptide inhibitor of the human FcRn:human IgG interaction
  作者：Adam R. Mezo、Kevin A. McDonnell、Alfredo Castro、Cara Fraley

  DOI：10.1016/j.bmc.2008.05.004

  日期：2008.6

  A family of five peptides was previously discovered by phage display techniques that binds to the human neonatal Fc receptor (FcRn) and inhibits the human IgG: human FcRn protein-protein interaction [Proc. Nat. Acad. Sci. U. S. A. 2008, 105, 2337-2342]. The consensus peptide motif consists of the sequence GHFGGXY where X is preferably a hydrophobic amino acid, and also includes a disul. de bridge enclosing 11-amino acids in varying positions about the consensus sequence. We describe herein the structure activity relationships of one of the five peptides in binding to FcRn using surface plasmon resonance and IgG: FcRn competition ELISA assays. Modi. cations of the peptide length, cyclization, and the incorporation of amino acid substitutions and dipeptide mimetics were studied. The most potent analogs exhibited a 50-to 100-fold improvement of in vitro activity over that of the phage-identified peptide sequence. (c) 2008 Elsevier Ltd. All rights reserved.