H-Tyr-NMe-D-Ala-Phe-NMe-Gly-NH2 | 1021852-90-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: H-Tyr-NMe-D-Ala-Phe-NMe-Gly-NH2
• 英文别名: SB0306；H-Tyr-NMe-D-Ala-Phe-Sar-NH2；(2S)-2-amino-N-[(2R)-1-[[(2S)-1-[(2-amino-2-oxoethyl)-methylamino]-1-oxo-3-phenylpropan-2-yl]amino]-1-oxopropan-2-yl]-3-(4-hydroxyphenyl)-N-methylpropanamide
• CAS: 1021852-90-3
• 化学式: C₂₅H₃₃N₅O₅
• 分子量: 483.568
• InChiKey: GRHNSLXBGRDMSP-CZAAIQMYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  159
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  叔丁氧羰酰基肌氨酸 、 BOC-L-苯丙氨酸 、 丁氧羰基-O-2,6-二氯苄基-L-酪氨酸 、 BOC-N-甲基-D-丙氨酸 生成 H-Tyr-NMe-D-Ala-Phe-NMe-Gly-NH2
  参考文献：
  名称：

  Blood−Brain Barrier Penetration by Two Dermorphin Tetrapeptide Analogues: Role of Lipophilicity vs Structural Flexibility

  摘要：

  Two dermorphin analogues having an almost identical structure but different structural flexibility were compared for opioid activity. In I the aromatic side chains were incorporated into a lactam structure, while in 2 N-amide alkylation was retained but the side chains were flexible. Both compounds produced comparable antinociceptive effects in the mouse tail flick test after peripheral administration. This indicates that lipophilicity, rather than side chain flexibility, is the key determinant for blood-CNS barrier penetration.

  DOI：

  10.1021/jm701404s

文献信息

• Blood−Brain Barrier Penetration by Two Dermorphin Tetrapeptide Analogues: Role of Lipophilicity vs Structural Flexibility
  作者：Steven Ballet、Aleksandra Misicka、Piotr Kosson、Carole Lemieux、Nga N. Chung、Peter W. Schiller、Andrzej W. Lipkowski、Dirk Tourwé

  DOI：10.1021/jm701404s

  日期：2008.4.1

  Two dermorphin analogues having an almost identical structure but different structural flexibility were compared for opioid activity. In I the aromatic side chains were incorporated into a lactam structure, while in 2 N-amide alkylation was retained but the side chains were flexible. Both compounds produced comparable antinociceptive effects in the mouse tail flick test after peripheral administration. This indicates that lipophilicity, rather than side chain flexibility, is the key determinant for blood-CNS barrier penetration.