RYYRWK-NH2 | 1053260-81-3

• 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: RYYRWK-NH2
• 英文别名: H-Arg-Tyr-Tyr-Arg-Trp-Lys-NH2；(2S)-6-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-amino-5-(diaminomethylideneamino)pentanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]hexanamide
• CAS: 1053260-81-3
• 化学式: C₄₇H₆₇N₁₅O₈
• 分子量: 970.145
• InChiKey: JPVNPXVTJUWXHM-WYLSNLDWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  70
• 可旋转键数：
  29
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  426
• 氢给体数：
  15
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  Ac-RYYRWK-NH2 生成 RYYRWK-NH2
  参考文献：
  名称：

  Synthesis and biological activity of novel small peptides with aminophosphonates moiety as NOP receptor ligands

  摘要：

  The aim of the present study was the synthesis and the biological screening of new analogs of Ac-RYYRWK-NH(2), modified at the N-terminal with 1-[(methoxyphosphono)methylamino]cycloalkanecarboxylic acids. The four newly synthesized ligands for the nociceptin/orphanin FQ (N/OFQ) receptor (NOP) have been prepared by solid-phase peptide synthesis-Fmoc-strategy. These compounds were tested for agonistic activity in vitro on electrically stimulated smooth-muscle preparations isolated from vas deferens of Wistar rats. Our data showed that substitution of Arg at position 1 with aminophosphonates moiety decreased significantly the affinity of ligands to the NOP receptor. Furthermore, the enlargement of the cycle (with 5-8 carbon atoms) additionally diminished both the activity and the selectivity for NOP-receptor.

  DOI：

  10.1007/s00726-010-0624-1

文献信息

• Synthesis and changes in affinity for NOP and opioid receptors of novel hexapeptides containing β2-tryptophan analogues
  作者：Rositsa Zamfirova、Nikola Pavlov、Petar Todorov、Polina Mateeva、Jean Martinez、Monique Calmès、Emilia Naydenova

  DOI：10.1016/j.bmcl.2013.05.064

  日期：2013.7

  We report the synthesis and the biological activity of new analogues of Ac-RFMWMK-NH2 and Ac-RYYRWK-NH2, modified in position 4 and 5, respectively, with incorporation of newly synthesized beta(2)-tryptophan analogues. Trp was substituted by the (S)-2-(1-methyl-1H-indol-3-yl)propionic residue or by (S)-2-(5-methoxy-1H-indol-3-yl)propionic residue. The biological activity (pEC(50) and E-max) of these compounds was tested on electrically stimulated preparations of rat vas deferens. The 5-methoxy beta-tryptophan group reverses the affinity of the compounds. (C) 2013 Elsevier Ltd. All rights reserved.