Boc-Tyr-(R)-βPrs-Phe-Phe-NH2 | 1251071-94-9

• 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: Boc-Tyr-(R)-βPrs-Phe-Phe-NH2
• 英文别名: tert-butyl N-[(2S)-1-[(3R)-3-[[(2S)-1-[[(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]sulfamoyl]pyrrolidin-1-yl]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]carbamate
• CAS: 1251071-94-9
• 化学式: C₃₆H₄₅N₅O₈S
• 分子量: 707.848
• InChiKey: UFVBXTPSZHPOCP-BHSUFKTOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  50
• 可旋转键数：
  16
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  206
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  Boc-Tyr-(R)-βPrs-Phe-Phe-NH2 、 三氟乙酸 在 水 作用下， 反应 2.0h， 生成 (2S)-2-[[(2S)-2-[[(3R)-1-[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]pyrrolidin-3-yl]sulfonylamino]-3-phenylpropanoyl]amino]-3-phenylpropanamide;2,2,2-trifluoroacetic acid
  参考文献：
  名称：

  Synthesis and activity of endomorphin-2 and morphiceptin analogues with proline surrogates in position 2

  摘要：

  The opioid agonists endomorphins (Tyr-Pro-Trp-Phe-NH(2); EM1 and Tyr-Pro-Phe-Phe-NH(2); EM2) and morphiceptin (Tyr-Pro-Phe-Pro-NH(2)) exhibit an extremely high selectivity for mu-opioid receptor. Here a series of novel EM2 and morphiceptin analogues containing in place of the proline at position 2 the S and R residues of beta-homologues of proline (HPro), of 2-pyrrolidinemethanesulphonic acid (HPrs) and of 3-pyrrolidinesulphonic acid (beta Prs) have been synthesized and their binding affinity and functional activity have been investigated. The highest p-receptor affinity is shown by [(S)beta Prs(2)]EM2 analogue (6e) which represents the first example of a beta-sulphonamido analogue in the field of mold peptides. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.07.022
• 作为产物：
  描述：

  (2S)-2-[[(3R)-1-[(2S)-3-(4-hydroxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]pyrrolidin-3-yl]sulfonylamino]-3-phenylpropanoic acid 、 L-苯丙氨酰胺盐酸盐 在 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 二氯甲烷 为溶剂， 以48%的产率得到Boc-Tyr-(R)-βPrs-Phe-Phe-NH2
  参考文献：
  名称：

  Synthesis and activity of endomorphin-2 and morphiceptin analogues with proline surrogates in position 2

  摘要：

  The opioid agonists endomorphins (Tyr-Pro-Trp-Phe-NH(2); EM1 and Tyr-Pro-Phe-Phe-NH(2); EM2) and morphiceptin (Tyr-Pro-Phe-Pro-NH(2)) exhibit an extremely high selectivity for mu-opioid receptor. Here a series of novel EM2 and morphiceptin analogues containing in place of the proline at position 2 the S and R residues of beta-homologues of proline (HPro), of 2-pyrrolidinemethanesulphonic acid (HPrs) and of 3-pyrrolidinesulphonic acid (beta Prs) have been synthesized and their binding affinity and functional activity have been investigated. The highest p-receptor affinity is shown by [(S)beta Prs(2)]EM2 analogue (6e) which represents the first example of a beta-sulphonamido analogue in the field of mold peptides. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.07.022

文献信息

• Synthesis and activity of endomorphin-2 and morphiceptin analogues with proline surrogates in position 2
  作者：Cesare Giordano、Anna Sansone、Annalisa Masi、Gino Lucente、Pasqualina Punzi、Adriano Mollica、Francesco Pinnen、Federica Feliciani、Ivana Cacciatore、Peg Davis

  DOI：10.1016/j.ejmech.2010.07.022

  日期：2010.10

  The opioid agonists endomorphins (Tyr-Pro-Trp-Phe-NH(2); EM1 and Tyr-Pro-Phe-Phe-NH(2); EM2) and morphiceptin (Tyr-Pro-Phe-Pro-NH(2)) exhibit an extremely high selectivity for mu-opioid receptor. Here a series of novel EM2 and morphiceptin analogues containing in place of the proline at position 2 the S and R residues of beta-homologues of proline (HPro), of 2-pyrrolidinemethanesulphonic acid (HPrs) and of 3-pyrrolidinesulphonic acid (beta Prs) have been synthesized and their binding affinity and functional activity have been investigated. The highest p-receptor affinity is shown by [(S)beta Prs(2)]EM2 analogue (6e) which represents the first example of a beta-sulphonamido analogue in the field of mold peptides. (C) 2010 Elsevier Masson SAS. All rights reserved.