摘要
合成了一系列未见文献报道的含有杂环的寡肽手性胺。采用苯并三氮唑-N,N,N,N四甲基脲六氟磷酸盐(HBTU)缩合剂,以N,N-二异丙基乙胺(DIPEA)为催化剂,将手性氨基酸Boc-L-脯氨酸、Boc-L-苯丙氨酸、Boc-L-色氨酸、L-脯氨酸甲酯盐酸盐、L-苯丙氨酸甲酯盐酸盐、L-色氨酸甲酯盐酸盐和取代苄胺,按照由N端向C端逆向接肽的合成策略,合成了8个化合物(表1),收率为70.2%~81.7%,所合成的化合物经IR、~1H NMR、^(13)C NMR、^(19)F NMR及UPLC-ESI-MS/MS等谱图分析进行了结构确认与表征,并对合成路线和方法进行优化与讨论。
A series of oligopeptides chiral amines containing heterocyclic were synthesised and have not been reported. The method of condensation of benzotriazole-N,N,N,N-tetramethyluronium hexafluorophosphate（ HBTU） to form amide was carried out by using N,N-diisopropylethylamine（ DIPEA） as catalyst,chiral amino acids Boc-L-proline,Boc-L-phenylalanine,Boc-L-tryptophan,L-proline methyl ester hydrochloride,L-phenylalanine methyl ester hydrochloride,L-tryptophan methyl ester hydrochloride and substituted benzylamine were used as raw materials. Eight dipeptide chiral amines（ Table 1） were synthesized by liquid phase method according to the synthesis strategy of N-terminal to C-terminal reverse peptides,yield is 70. 2 % - 81. 7 %. The structures of the synthesized compounds were characterized by IR,^1H NMR,^13C NMR,^19F NMR and UPLC-ESI-MS/MS mass spectrometry.
作者
廖鹏
胡仕琴
刘静姿
何彬
LIAO Peng;HU Shi-qin;LIU Jing-zi;HE Bin(School of Pharmacy, Guizhou Medical University, Guiyang 550004, Guizhou, China;Engineering Research Center for the Development and Application of Ethnic Medicine and TCM, Ministry of Education, Guiyang 550004, Guizhou, China;Guizhou Provincial Key Laboratory of Pharmaceutics, Guiyang 550004, Guizhou, China)
出处
《合成材料老化与应用》
2018年第1期41-47,共7页
Synthetic Materials Aging and Application
基金
国家自然科学基金(No.81160385)
贵州省科技厅(黔科合SY字[2012]3103)
贵州省教育厅([黔省专合字2012]89号)
贵阳医学院基金(YJ 2014-17)
关键词
手性胺
二肽合成
杂环
chiral amine, dipeptide synthesis, heterocyclic
