H-Pro-Phe-NH2 hydrochloride | 97372-02-6

• 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: H-Pro-Phe-NH2 hydrochloride
• 英文别名: amine pro phe amide HCl；N-L-prolyl-L-phenylalanine amide; hydrochloride；N-L-Prolyl-L-phenylalanin-amid; Hydrochlorid；H-Pro-Phe-NH2 HCl；(2S)-N-[(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]pyrrolidine-2-carboxamide;hydrochloride
• CAS: 97372-02-6
• 化学式: C₁₄H₁₉N₃O₂*ClH
• 分子量: 297.785
• InChiKey: FAFBGWPFTZCDIF-FXMYHANSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.37
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  84.2
• 氢给体数：
  4
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  H-Pro-Phe-NH2 hydrochloride 在 盐酸 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 H-Tyr(2,6-diMe)-Pro-Phe-NH2
  参考文献：
  名称：

  Structural studies of [2′,6′-dimethyl-l-tyrosine1]endomorphin-2 analogues: enhanced activity and cis orientation of the Dmt-Pro amide bond

  摘要：

  Analogues of endomorphin-2 (EM-2: Tyr-Pro-Phe-Phe-NH2) (1) were designed to examine the importance of each residue on mu-opioid receptor interaction. Replacement of Tyr(1) by 2',6'-dimethyl-L-tyrosine (Dmt) (9-12) exerted profound effects: [Dmt(1)]EM-2 (9) elevated mu-opioid affinity 4.6-fold (K(i)mu = 0.15 nM) yet selectivity fell 330-fold as delta-affinity rose (K(i)delta = 28.2 nM). This simultaneous increased mu- and delta-receptor bioactivities resulted in dual agonism (IC50 = 0.07 and 1.87 nM, respectively). While substitution of Phe(4) by a phenethyl group (4) decreased mu affinity (K(i)mu 13.3 nM), the same derivative containing Dmt (12) was comparable to EM-2 but also acquired weak delta antagonism (pA(2) = 7.05). H-1 NMR spectroscopy revealed a trans configuration (1:2 to 1:3, cis/trans) in the Tyr-Pro amide bond, but a cis configuration (5:3 to 13:7, cis/trans) with Dmt-Pro analogues. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00068-3
• 作为产物：
  描述：

  L-苯丙氨酰胺盐酸盐 在 N-甲基吗啉 、 盐酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 生成 H-Pro-Phe-NH2 hydrochloride
  参考文献：
  名称：

  Structural studies of [2′,6′-dimethyl-l-tyrosine1]endomorphin-2 analogues: enhanced activity and cis orientation of the Dmt-Pro amide bond

  摘要：

  Analogues of endomorphin-2 (EM-2: Tyr-Pro-Phe-Phe-NH2) (1) were designed to examine the importance of each residue on mu-opioid receptor interaction. Replacement of Tyr(1) by 2',6'-dimethyl-L-tyrosine (Dmt) (9-12) exerted profound effects: [Dmt(1)]EM-2 (9) elevated mu-opioid affinity 4.6-fold (K(i)mu = 0.15 nM) yet selectivity fell 330-fold as delta-affinity rose (K(i)delta = 28.2 nM). This simultaneous increased mu- and delta-receptor bioactivities resulted in dual agonism (IC50 = 0.07 and 1.87 nM, respectively). While substitution of Phe(4) by a phenethyl group (4) decreased mu affinity (K(i)mu 13.3 nM), the same derivative containing Dmt (12) was comparable to EM-2 but also acquired weak delta antagonism (pA(2) = 7.05). H-1 NMR spectroscopy revealed a trans configuration (1:2 to 1:3, cis/trans) in the Tyr-Pro amide bond, but a cis configuration (5:3 to 13:7, cis/trans) with Dmt-Pro analogues. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00068-3

文献信息

• Incorporation of carbohydrates and peptides into large triazine-based screening libraries using automated parallel synthesis
  作者：Gary R. Gustafson、Carmen M. Baldino、Mary-Margaret E. O'Donnell、Adrian Sheldon、Robert J. Tarsa、Christopher J. Verni、David L. Coffen

  DOI：10.1016/s0040-4020(98)00134-3

  日期：1998.4

  A procedure for the sequential, selective derivatization of cyanuric chloride that allows for the incorporation of carbohydrates and peptides has been elucidated. As a result, large combinatorial arrays of individual derivatives, over 40,000 in all, have been produced in 50 mu mole quantities using automated parallel solution phase synthesis. The use of this technology in a search for protease inhibitors, glycopeptide surrogates and other bioactive compound classes will also be discussed. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.