2’6’-Dmt-D-Arg-Phe Orn-NH2

• 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: 2’6’-Dmt-D-Arg-Phe Orn-NH2
• 英文别名: 2',6'-Dmt-D-Arg-Phe-Orn-NH₂；Dmt-d-Arg-Phe-Orn-NH2；(2S)-5-amino-2-[[(2S)-2-[[(2R)-2-[[(2S)-2-amino-3-(4-hydroxy-2,6-dimethylphenyl)propanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]amino]-3-phenylpropanoyl]amino]pentanamide
• 化学式: C₃₁H₄₇N₉O₅
• 分子量: 625.771
• InChiKey: YJZGZJUNCTZJLV-SSUZURRFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  45
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  267
• 氢给体数：
  9
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  BOC-L-苯丙氨酸 、 N-叔丁氧羰基-N'-甲苯磺酰基-L-精氨酸 、 N^d-Fmoc-L-鸟氨酸 、 N-Boc-O-Boc-2',6'-dimethyl-L-tyrosine 生成 2’6’-Dmt-D-Arg-Phe Orn-NH2
  参考文献：
  名称：

  Synthesis and in vitro opioid activity profiles of DALDA analogues

  摘要：

  The tetrapeptide DALDA (H-Tyr-D-Arg-Phe-Lys-NH2) is a polar and selective mu agonist showing poor penetration of the placental and blood-brain barriers. In an effort to enhance the potency of DALDA, analogues containing 2',6'-dimethyltyrosine (Dmt), N,2',6'-trimethyltyrosine (Tmt), 2'-methyltyrosine (Mmt) or 2'-hydroxy,6'-methyltyrosine (Hmt) in place of Tyr(1), or Om or alpha,gamma -diaminobutyric acid (A(2)bu) in place of Lys(4), were synthesized. All compounds displayed high mu receptor selectivity in the rat and guinea pig brain membrane binding assays and most of them were more potent mu agonists than DALDA in the mu receptor-representative guinea pig ileum assay, with [Dmt(1)]DALDA showing the highest potency. Because of its extraordinary mu agonist potency, high mu selectivity, polar character (charge of 3+) and metabolic stability, [Dmt(1)]DALDA has potential for use in obstetrical or peripheral analgesia. (C) 2000 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(00)01171-5

文献信息

• Synthesis and in vitro opioid activity profiles of DALDA analogues
  作者：Peter W Schiller、Thi M.-D Nguyen、Irena Berezowska、Sébastien Dupuis、Grazyna Weltrowska、Nga N Chung、Carole Lemieux

  DOI：10.1016/s0223-5234(00)01171-5

  日期：2000.10

  The tetrapeptide DALDA (H-Tyr-D-Arg-Phe-Lys-NH2) is a polar and selective mu agonist showing poor penetration of the placental and blood-brain barriers. In an effort to enhance the potency of DALDA, analogues containing 2',6'-dimethyltyrosine (Dmt), N,2',6'-trimethyltyrosine (Tmt), 2'-methyltyrosine (Mmt) or 2'-hydroxy,6'-methyltyrosine (Hmt) in place of Tyr(1), or Om or alpha,gamma -diaminobutyric acid (A(2)bu) in place of Lys(4), were synthesized. All compounds displayed high mu receptor selectivity in the rat and guinea pig brain membrane binding assays and most of them were more potent mu agonists than DALDA in the mu receptor-representative guinea pig ileum assay, with [Dmt(1)]DALDA showing the highest potency. Because of its extraordinary mu agonist potency, high mu selectivity, polar character (charge of 3+) and metabolic stability, [Dmt(1)]DALDA has potential for use in obstetrical or peripheral analgesia. (C) 2000 Editions scientifiques et medicales Elsevier SAS.