N-propargyl N-carboxyanhydride | 1228093-70-6

• 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: N-propargyl N-carboxyanhydride
• 英文别名: 3-(Prop-2-yn-1-yl)oxazolidine-2,5-dione；3-prop-2-ynyl-1,3-oxazolidine-2,5-dione
• CAS: 1228093-70-6
• 化学式: C₆H₅NO₃
• 分子量: 139.111
• InChiKey: APROCNDUGOHCLD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-((tert-butoxycarbonyl)(prop-2-yn-1-yl)-amino)acetic acid 在 三氯化磷 作用下， 以 二氯甲烷 为溶剂， 以55%的产率得到N-propargyl N-carboxyanhydride
  参考文献：
  名称：

  Synthesis and Characterization of Cyclic Brush-Like Polymers by N-Heterocyclic Carbene-Mediated Zwitterionic Polymerization of N-Propargyl N-Carboxyanhydride and the Grafting-to Approach

  摘要：

  Cyclic brush-like polymers were synthesized by tandem organo-mediated zwitterionic polymerization and a grafting-to approach. The cyclic polymer backbone, consisting of poly(N-propargylglycine) (c-PNPG), was synthesized by an N-heterocyclic carbene (NHC)-mediated zwitterionic ring-opening polymerization of N-propargyl N-carboxyanhydride. The polymerization proceeds in a quasi-living manner, allowing access to c-PNPG of well-defined chain length. The cyclic architecture of the polymers was verified by size exclusion chromatography (SEC) and mass spectroscopy (MS), as well as scanning probe characterization. Poly(ethylene glycol) functionalized with azido end-groups was subsequently grafted onto the c-PNPG by the copper-mediated azide/alkyne cycloaddition reaction (CuAAC). The side chain grafting density was determined by H-1 NNIR spectroscopy and SEC analysis. The grafting efficiency is low (<19%) when the cyclic backbone is comprised of a c-PNPG homopolymer. The efficiency can be significantly improved (up to 93%) by utilizing cyclic poly(N-propargylglycine)-ran-poly(N-butylglycine) random copolymers (c-PNPG-r-PNBG). This has been attributed to the ease of access to the propargyl groups in c-PNPG and c-PNPG-ran-PNBG: the strong tendency of the former to aggregate in common organic solvents (including the CuAAC reaction medium) restricts access to the propargyl groups.

  DOI：

  10.1021/ma201948u

文献信息

• 一种均聚电解质复合囊泡及其制备方法以及抗菌囊泡、包载疏水性物质的囊泡和抗黏附囊泡
  申请人：青岛科技大学

  公开号：CN113476614B

  公开（公告）日：2023-08-25

  本发明涉及生物高分子技术领域，提供了一种均聚电解质复合囊泡及其制备方法以及抗菌囊泡、包载疏水性物质的囊泡和抗黏附囊泡。本发明利用两种具有相反电荷的聚类肽通过静电作用自组装成稳定的纳米级均聚电解质复合囊泡，该囊泡具有较好的膜渗透特性，在酸性条件下具有较好的杀菌效果，能够包载疏水性物质，且囊泡表面具有两性离子的特征，具有较好的抗蛋白质黏附性能。本发明提供的抗菌囊泡具有优异的灭菌能力，尤其是对革兰氏阳性细菌的灭菌能力强；本发明提供的包载疏水性物质的囊泡可包载各种疏水性的染料或药物，实现药物的高效递送；进一步的，经过表面的轻度交联后囊泡更加稳定，抗黏附性更好，且能够对内部药物的释放速率进行有效调控。
• Synthesis and Characterization of Cyclic Brush-Like Polymers by <i>N</i>-Heterocyclic Carbene-Mediated Zwitterionic Polymerization of <i>N</i>-Propargyl <i>N</i>-Carboxyanhydride and the Grafting-to Approach
  作者：Samuel H. Lahasky、Wilson K. Serem、Li Guo、Jayne C. Garno、Donghui Zhang

  DOI：10.1021/ma201948u

  日期：2011.12.13

  Cyclic brush-like polymers were synthesized by tandem organo-mediated zwitterionic polymerization and a grafting-to approach. The cyclic polymer backbone, consisting of poly(N-propargylglycine) (c-PNPG), was synthesized by an N-heterocyclic carbene (NHC)-mediated zwitterionic ring-opening polymerization of N-propargyl N-carboxyanhydride. The polymerization proceeds in a quasi-living manner, allowing access to c-PNPG of well-defined chain length. The cyclic architecture of the polymers was verified by size exclusion chromatography (SEC) and mass spectroscopy (MS), as well as scanning probe characterization. Poly(ethylene glycol) functionalized with azido end-groups was subsequently grafted onto the c-PNPG by the copper-mediated azide/alkyne cycloaddition reaction (CuAAC). The side chain grafting density was determined by H-1 NNIR spectroscopy and SEC analysis. The grafting efficiency is low (<19%) when the cyclic backbone is comprised of a c-PNPG homopolymer. The efficiency can be significantly improved (up to 93%) by utilizing cyclic poly(N-propargylglycine)-ran-poly(N-butylglycine) random copolymers (c-PNPG-r-PNBG). This has been attributed to the ease of access to the propargyl groups in c-PNPG and c-PNPG-ran-PNBG: the strong tendency of the former to aggregate in common organic solvents (including the CuAAC reaction medium) restricts access to the propargyl groups.