非天然氨基酸的N-叔丁氧羰基化研究

A Study on N-tert-butoxycarbonylation of Non-natural Amino Acids

目的:探讨非天然氨基酸N-叔丁氧羰基化反应的适宜溶剂系统。方法:以酪氨酸作对照,分别将含4-甲基、4-甲氧基、4-氯及2-萘基等不同苯基取代基的非天然苯丙氨酸在水-叔丁醇和水-四氢呋喃两种溶剂系统中进行N-叔丁氧羰基化反应,比较收率。结果:在水-四氢呋喃系统中随着苯丙氨酸脂溶性增大,N-叔丁氧羰基化收率提高。结论:水-四氢呋喃溶剂系统较适用于脂溶性大的非天然氨基酸N-叔丁氧羰基化,收率高,后处理简单。

Objective： To study the solvent systems suitable for N-tert-butoxycarbonylation of non-natural amino acids, Methods： The N-tert-butoxycarbonylations of non-natural phenylalanines substituted with 4-OH, 4-Me, 4-MeO, 4-Cl and 2-naphthyl were conducted respectively in water-tert-tiarybutanol and water-THF to compare the yields there of. Results： The N-tert-butoxycarbonylation of lipophilic phenylalanines in THF system gave a higher yield than in other solvent systems. Conclusion： Water-THF system is suitable for N- tert-butoxycarbonylation of lipophilic non-natural amino acids, with high yield and simple post-treatment.