N-tert-butyloxycarbonyl-L-phenylalanyl-D-allylglycine methyl ester | 158840-24-5

• 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: N-tert-butyloxycarbonyl-L-phenylalanyl-D-allylglycine methyl ester
• 英文别名: Boc-Phe-D-Gly(allyl)-OMe；methyl (2R)-2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]amino]pent-4-enoate
• CAS: 158840-24-5
• 化学式: C₂₀H₂₈N₂O₅
• 分子量: 376.453
• InChiKey: HAGSUBDQILYPMJ-CVEARBPZSA-N

物化性质

• 沸点：
  538.8±50.0 °C(predicted)
• 密度：
  1.113±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-tert-butyloxycarbonyl-L-phenylalanyl-D-allylglycine methyl ester 、 三氟乙酸 以 二氯甲烷 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Synthesis of Stable and Potent δ/μ Opioid Peptides:  Analogues of H-Tyr-c[d-Cys-Gly-Phe-d-Cys]-OH by Ring-Closing Metathesis

  摘要：

  Ring-closing metathesis has emerged as a powerful tool in organic synthesis for generating cyclic structures via C-C double bond formation. Recently, it has been successfully used in peptide chemistry for obtaining cyclic molecules bridged through an olefin unit in place of the usual disulfide bond. Here, we describe this approach for obtaining cyclic olefin bridged analogues of H-Tyr-c[D-Cys-Gly-Phe-Cys]-OH. The synthesis of the new ligands was performed using the second generation Grubbs' catalyst. The resulting cis-8 (cDADAE) and trans-9 (tDADAE) were fully characterized and tested at delta, mu, and kappa opioid receptors. Also the linear precursor 13 (lDADAE) and the hydrogenated derivative 11(rDADAE) also were tested. All the cyclic products containing a olefinic bond are slightly selective but highly active and potent for the delta and mu opioid receptors. Activity toward the kappa opioid receptors was absent or very low.

  DOI：

  10.1021/jm061048b
• 作为产物：
  描述：

  Boc-D-烯丙基甘氨酸 在 N-甲基吗啉 、 氯化亚砜 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 N-tert-butyloxycarbonyl-L-phenylalanyl-D-allylglycine methyl ester
  参考文献：
  名称：

  Synthesis of Stable and Potent δ/μ Opioid Peptides:  Analogues of H-Tyr-c[d-Cys-Gly-Phe-d-Cys]-OH by Ring-Closing Metathesis

  摘要：

  Ring-closing metathesis has emerged as a powerful tool in organic synthesis for generating cyclic structures via C-C double bond formation. Recently, it has been successfully used in peptide chemistry for obtaining cyclic molecules bridged through an olefin unit in place of the usual disulfide bond. Here, we describe this approach for obtaining cyclic olefin bridged analogues of H-Tyr-c[D-Cys-Gly-Phe-Cys]-OH. The synthesis of the new ligands was performed using the second generation Grubbs' catalyst. The resulting cis-8 (cDADAE) and trans-9 (tDADAE) were fully characterized and tested at delta, mu, and kappa opioid receptors. Also the linear precursor 13 (lDADAE) and the hydrogenated derivative 11(rDADAE) also were tested. All the cyclic products containing a olefinic bond are slightly selective but highly active and potent for the delta and mu opioid receptors. Activity toward the kappa opioid receptors was absent or very low.

  DOI：

  10.1021/jm061048b

文献信息

• Synthesis of Stable and Potent δ/μ Opioid Peptides:  Analogues of H-Tyr-<i>c</i>[<scp>d</scp>-Cys-Gly-Phe-<scp>d</scp>-Cys]-OH by Ring-Closing Metathesis
  作者：Adriano Mollica、Giovanni Guardiani、Peg Davis、Shou-Wu Ma、Frank Porreca、Josephine Lai、Luisa Mannina、Anatoli P. Sobolev、Victor J. Hruby

  DOI：10.1021/jm061048b

  日期：2007.6.1

  Ring-closing metathesis has emerged as a powerful tool in organic synthesis for generating cyclic structures via C-C double bond formation. Recently, it has been successfully used in peptide chemistry for obtaining cyclic molecules bridged through an olefin unit in place of the usual disulfide bond. Here, we describe this approach for obtaining cyclic olefin bridged analogues of H-Tyr-c[D-Cys-Gly-Phe-Cys]-OH. The synthesis of the new ligands was performed using the second generation Grubbs' catalyst. The resulting cis-8 (cDADAE) and trans-9 (tDADAE) were fully characterized and tested at delta, mu, and kappa opioid receptors. Also the linear precursor 13 (lDADAE) and the hydrogenated derivative 11(rDADAE) also were tested. All the cyclic products containing a olefinic bond are slightly selective but highly active and potent for the delta and mu opioid receptors. Activity toward the kappa opioid receptors was absent or very low.