五种胶原多肽基表面活性剂合成路线的理论和实验研究

Theoretical and experimental studies on the synthetic route of five kinds of collagen-peptide based surfactants

为了扩展胶原材料的应用范围,采用计算化学与实验相结合的方法,研究了胶原多肽基表面活性剂的适宜合成路线。以赖氨酸作为含侧链氨基胶原多肽模型,十五醛、1,2-环氧十五烷、丙烯酸十五酯、油酸酰氯和十五烷基磺酰氯作为表面活性剂疏水端原料模型,应用密度泛函理论对各反应物种进行优化。通过分析分子前线轨道能量、偶极矩、反应焓和反应自由能,发现赖氨酸与油酸酰氯或十五烷基磺酰氯的反应路线具有较强的理论可行性。实验测试结果与理论预测基本一致,在优化的反应条件下,胶原多肽与油酸酰氯反应的转化率为65.8%,产物贮藏稳定性好,当产物质量浓度为4g/L时,其表面张力可达40mN/m。

In order to expand the application scope of collagen materials, the rational synthetic route of collagen-peptide based surfactant was investigated by both computational chemistry and experimental methods. Lysine was used as a model of collagenous peptide with side chain amino, and pentadecanal, 1,2-pentadecene oxide, pentadecyl acrylate, oleoyl chloride and pentadecyl sulfonyl chloride were used as models of hydrophobic group-containing compounds. The geometrical configurations of these compounds were optimized based on density-functional theory. Afterwards, the energy of frontier molecular orbit, dipole moment, reaction enthalpies and Gibbs free energy were analyzed. The theoretical analysis indicated that lysine possessed high reaction activity with oleoyl chloride and pentadecyl sulfonyl chloride. Furthermore, the experimental study was performed and showed similar results with the theoretical analysis. Under the optimized reaction conditions, the conversion rate of collagen peptides reacting with oleoyl chloride was 65.8%, and the product showed good storage stability, and its surface tension reached 40 mN/m at 4 g/ L.