Synthesis of an unnatural amino acid for genetic incorporation into recombinant proteins.

• Main Author: Chia, Siew Meng.
• Other Authors: Liu Chuan Fa
• Format: Final Year Project
• Language: English
• Published: 2012
• Subjects: DRNTU::Science
• Online Access: http://hdl.handle.net/10356/49266
• Institution: Nanyang Technological University

An unnatural amino acid, azalysine, was synthesized using several proposed procedures with the general concept of using glutamic acid as starting material, followed by reduction of the side chain carboxyl into aldehyde and lastly the conversion of the aldehyde to hydrazine by reductive amination. Benzyl-protected glutamic acid was found to be more effective in the synthesis process as compared to Boc-protected glutamic acid. The benzyl protecting groups can be removed by catalytic hydrogenation using palladium black as catalyst. The azalysine obtained could be used for incorporation into recombinant proteins for applications such as detection of oxidized carbonyl-containing protein molecules, or labeling with reactive carbonyl-containing probes to visualize proteins in vivo so as to study protein localization, concentrations or dynamics.