(S)-Boc-β-Tyr | 439918-60-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-Boc-β-Tyr
• 英文别名: Boc-hβ³Tyr-OH；(3S)-4-(4-hydroxyphenyl)-3-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acid
• CAS: 439918-60-2
• 化学式: C₁₅H₂₁NO₅
• 分子量: 295.335
• InChiKey: HGENLNONQYCKJV-NSHDSACASA-N

物化性质

• 沸点：
  500.9±45.0 °C(Predicted)
• 密度：
  1.212±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  95.9
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-Boc-β-Tyr 在 盐酸 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 1,4-二氧六环 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 53.0h， 生成 β-Tyr-Pro-Trp-Phe-NH2 hydrochloride
  参考文献：
  名称：

  Endomorphin-1 Analogues Containing β-Proline Are μ-Opioid Receptor Agonists and Display Enhanced Enzymatic Hydrolysis Resistance

  摘要：

  In this paper we describe the synthesis and affinity toward the mu-opioid receptor of some tetrapeptides obtained from endomorphin-1, H-Tyr-Pro-Trp-Phe-NH2 (1), by substituting each amino acid in turn with its homologue. The ability to bind p-opioid receptors depends on the beta-amino acid, and in particular 4, which contains beta-L-Pro, has a K-1 in the nanomolar range. The peptides 4 and 5 are significantly more resistant to enzymatic hydrolysis than 1. The same compounds, as well as they-opioid receptor agonist DAMGO, produced a concentration-dependent inhibition of forskolin-stimulated cyclic AMP formation, thus behaving as mu-opioid agonists. These features suggest that this novel class of endomorphin-1 analogues may represent suitable candidates for the in vivo investigation as potential mu-opioid receptor agonists.

  DOI：

  10.1021/jm011059z
• 作为产物：
  描述：

  在 TEA 、 silver trifluoroacetate 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 (S)-Boc-β-Tyr
  参考文献：
  名称：

  Endomorphin-1 Analogues Containing β-Proline Are μ-Opioid Receptor Agonists and Display Enhanced Enzymatic Hydrolysis Resistance

  摘要：

  In this paper we describe the synthesis and affinity toward the mu-opioid receptor of some tetrapeptides obtained from endomorphin-1, H-Tyr-Pro-Trp-Phe-NH2 (1), by substituting each amino acid in turn with its homologue. The ability to bind p-opioid receptors depends on the beta-amino acid, and in particular 4, which contains beta-L-Pro, has a K-1 in the nanomolar range. The peptides 4 and 5 are significantly more resistant to enzymatic hydrolysis than 1. The same compounds, as well as they-opioid receptor agonist DAMGO, produced a concentration-dependent inhibition of forskolin-stimulated cyclic AMP formation, thus behaving as mu-opioid agonists. These features suggest that this novel class of endomorphin-1 analogues may represent suitable candidates for the in vivo investigation as potential mu-opioid receptor agonists.

  DOI：

  10.1021/jm011059z

文献信息

• Biological Active Analogues of the Opioid Peptide Biphalin: Mixed α/β³-Peptides
  作者：Adriano Mollica、Francesco Pinnen、Roberto Costante、Marcello Locatelli、Azzurra Stefanucci、Stefano Pieretti、Peg Davis、Josephine Lai、David Rankin、Frank Porreca、Victor J. Hruby

  DOI：10.1021/jm301456c

  日期：2013.4.25

  Natural residues of the dimeric opioid peptide Biphalin were replaced by the corresponding homo-beta(3) amino acids. The derivative 1 containing h beta(3) Phe in place of Phe showed good mu- and delta-receptor affinities (K-i(delta) = 0.72 nM; K-i(mu) = 1.1 nM) and antinociceptive activity in vivo together with an increased enzymatic stability in human plasma.