Non-covalent solid phase peptide synthesis in water using molecularly imprinted polymers

• Main Authors: Guo-Guang Lu, 呂國光
• Other Authors: Dar-Fu Tai
• Format: Others
• Language: zh-TW
• Published: 2011
• Online Access: http://ndltd.ncl.edu.tw/handle/39931458708796712368

碩士 === 國立東華大學 === 化學系 === 99 === In general, for solid phase peptide synthesis, resin bound amino acids are used and harsh condition is applied to remove non-proctected peptide from resin. The resin cannot be reuse further. Constructed molecular imprinted polymers as the molecular cavity, could form the polymer with recognition ability. Non-covalent solid phase peptide synthesis could be perform via binding ability between the cavity formed by molecular imprinting and correspondind template. First, we used N-benzylacrylamide (Bm), N,N’-Ethylenebisacrylamide (EBAA), 2,2’-Azobis-isobutyronitrile (AIBN) and Fmoc-Pro-OH to execute photochemical copolymerization, the polymer which absorbed Fmoc-Pro-OH was prepared. Then, we used second amino acid L-Valine and water-soluble coupling reagent N-(3-Dimethylaminopropyl)-N’-ethylcarbodiimide hydrochloride (EDC‧HCl) , using water as the solvent, executed coupling reaction with microwave assisted. We succeeded to obtain dipeptide Fmoc-Pro-Val-OH, the yield was 56.68 %. Thereafter, tripeptide Fmoc-Pro-Val-Pro-OH and tetrapeptide Fmoc-Pro-Val-Pro-Tyr-OH were synthesized in order, the yields were 61.44 % and 70.84 %. The peptide which had protecting group was obtained from non-covalent solid phase peptide synthesis after simple extraction, thereafter we could execute peptide cyclization, the molecular cavity could be use again.