Synthesis of dihydroimidazole derivatives and study of their binding affinity with lysine

• Main Authors: Hung-Yi Hsu, 許弘宜
• Other Authors: Chien-Chung Cheng
• Format: Others
• Language: zh-TW
• Published: 2004
• Online Access: http://ndltd.ncl.edu.tw/handle/05383754473483254402

碩士 === 淡江大學 === 化學學系 === 92 === The goal of this research is to synthesize 2-alkoxy-4,5-dihydroimidazole derivatives with various diamines and then subjected to prepare 2-alkylamino- 4,5-dihydroimidazole derivatives with primary amines. The formation of alkylamino-4,5-dihydroimidazole adduct is known to enhance the signal intensity in the analysis of mass spectroscopy. It provides a solution in the determination of the molecular weight of the trace amount of protein in proteomics research. The preparation of 2-alkoxy-4,5-dihydroimidazole was prepared through the three-steps according to literature procedures. In our lab, the use of tetraethyl orthocarbonate and diamine in the acid condition undergoes the one-step cycliztion given a reasonable yield. The various diamines were used to examine the reactivity and rate of the cyclization with the different functional groups. The alkoxy group of 2-alkoxy- 4,5-dihydroimidazole was further substituted with the primary amines such as benzylamine, lysine, and peptides containing lysine residues to form the alkylamino- 4,5-dihydroimidazole adducts. The result provides the understanding of the interaction and reactivity of 2-alkoxy-4,5-dihydroimidazole and lysine residues in protein. The enhancement of the sensitivity of mass spectroscopy offers a new strategy to determine the protein molecules in a low abundance in biological systems.