O-(4-pentenyl)-L-serine | 1219133-89-7

• 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: O-(4-pentenyl)-L-serine
• 英文别名: O-(pentyenyl)-L-serine；(2S)-2-amino-3-pent-4-enoxypropanoic acid
• CAS: 1219133-89-7
• 化学式: C₈H₁₅NO₃
• 分子量: 173.212
• InChiKey: NOJLQTHILHAHLS-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  12
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  72.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  三光气 、 O-(4-pentenyl)-L-serine 以 四氢呋喃 为溶剂， 反应 16.0h， 以83%的产率得到O-(4-pentene)-L-serine N-carboxylanhydride
  参考文献：
  名称：

  Water-Soluble Poly(l-serine)s with Elongated and Charged Side-Chains: Synthesis, Conformations, and Cell-Penetrating Properties

  摘要：

  Water-soluble poly(L-serine)s bearing long side-chain with terminal charge groups were synthesized via ring-opening polymerization of O-pentenyl-L-serine N-carbox-yanhydride followed by thiol-ene reactions. These side-chain modified poly(L-serine)s adopt beta-sheet conformation in aqueous solution with excellent stability against changes in pH and temperature. These water-soluble poly(L-serine) derivatives with charged side-chain functional groups and stable beta-sheet conformations showed membrane-penetrating capabilities in different cell lines with low cytotoxicity.

  DOI：

  10.1021/bm3009445
• 作为产物：
  描述：

  5-溴-1-戊烯 在 盐酸 、 sodium hydride 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.5h， 生成 O-(4-pentenyl)-L-serine
  参考文献：
  名称：

  Water-Soluble Poly(l-serine)s with Elongated and Charged Side-Chains: Synthesis, Conformations, and Cell-Penetrating Properties

  摘要：

  Water-soluble poly(L-serine)s bearing long side-chain with terminal charge groups were synthesized via ring-opening polymerization of O-pentenyl-L-serine N-carbox-yanhydride followed by thiol-ene reactions. These side-chain modified poly(L-serine)s adopt beta-sheet conformation in aqueous solution with excellent stability against changes in pH and temperature. These water-soluble poly(L-serine) derivatives with charged side-chain functional groups and stable beta-sheet conformations showed membrane-penetrating capabilities in different cell lines with low cytotoxicity.

  DOI：

  10.1021/bm3009445