(2-(naphthalen-2-yl)acetyl)-D-phenylalanyl-D-phenylalanyl-D-lysine | 1259528-78-3

• 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: (2-(naphthalen-2-yl)acetyl)-D-phenylalanyl-D-phenylalanyl-D-lysine
• CAS: 1259528-78-3
• 化学式: C₃₆H₄₀N₄O₅
• 分子量: 608.737
• InChiKey: BDDZUCDMOGDPJK-XWHIBYANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.54
• 重原子数：
  45.0
• 可旋转键数：
  16.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  150.62
• 氢给体数：
  5.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2-(naphthalen-2-yl)acetyl)-D-phenylalanyl-D-phenylalanyl-D-lysine 、 奥沙拉嗪 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.25h， 生成 5-[[3-[[(5R)-5-carboxy-5-[[(2R)-2-[[(2R)-2-[(2-naphthalen-2-ylacetyl)amino]-3-phenylpropanoyl]amino]-3-phenylpropanoyl]amino]pentyl]carbamoyl]-4-hydroxyphenyl]diazenyl]-2-hydroxybenzoic acid
  参考文献：
  名称：

  Molecular Nanofibers of Olsalazine Form Supramolecular Hydrogels for Reductive Release of an Anti-inflammatory Agent

  摘要：

  Conjugation of tripeptide derivatives with olsalazine, a clinically used anti-inflammatory prodrug, yields small molecules that self-assemble in water to form supramolecular hydrogels that undergo a gel-to-sol phase transition upon reduction, resulting in the controlled release of 5-aminosalicylic acid as the anti-inflammatory agent. This methodology will ultimately lead to new biomaterials for site-specific drug delivery.

  DOI：

  10.1021/ja109269v
• 作为产物：
  描述：

  2-萘乙酸 在 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 水 为溶剂， 生成 (2-(naphthalen-2-yl)acetyl)-D-phenylalanyl-D-phenylalanyl-D-lysine
  参考文献：
  名称：

  Design and synthesis of nanofibers of self-assembled de novo glycoconjugates towards mucosal lining restoration and anti-inflammatory drug delivery

  摘要：

  The medical practice for IBD is solely based on anti-inflammatory drugs, but the outcome is far from ideal. Our long-term research goal is to seek a better clinical outcome by combining the anti-inflammatory therapy with physical mucus layer restoration. As the first step towards that objective, we choose to develop self-assembled hydrogels of de novo glycoconjugates that consist of anti-inflammatory drugs and glycopeptides. By covalently linking peptides (e.g., nap-phe-phe-lys), saccharides (e.g., glucosamine), and an anti-inflammatory drug (i.e., olsalazine), we have demonstrated that the obtained molecules self-assemble in water to form hydrogels composed of 3D networks of the nanofibers under acidic conditions. We also confirmed that the resulting glycoconjugates are cell compatible. However, the preliminary assessment of the efficacy of the hydrogels on the murine model is inconclusive, which warrants further investigation and molecular engineering. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2016.07.057

文献信息

• Enzymatic formation of a photoresponsive supramolecular hydrogel
  作者：Xinming Li、Yuan Gao、Yi Kuang、Bing Xu

  DOI：10.1039/c0cc00163e

  日期：——

  This paper reports the first example of the use of an enzymatic reaction to generate a photoresponsive hydrogelator, which represents a convenient route to expand the scope of optically controlled molecular self-assembly in water.

  本文首次报道了利用酶促反应生成光致伸缩性水凝胶剂的实例，为扩大水中光控分子自组装的范围提供了一条便捷的途径。