2010 Summer NC State Undergraduate Research Symposium

Session Time : 8/5/10 1:00 PM - 8/5/10 4:00 PM

Content Area : NSF Chemistry REU

Student Presenters :
Ana Victoria Morales Chemistry

Mentors and/or Co-Authors :
Alexander Deiters Chemistry

Abstract Title : Photo-Activated and Photo-Crosslinkable Unnatural Amino Acids for Unnatural Amino Acid Mutagenesis

Abstract :
Recent developments in unnatural amino acid mutagenesis in bacterial and mammalian cells with an expanded genetic code have created a demand for novel and useful unnatural amino acids, in order to better investigate and manipulate the biological and chemical properties of proteins. Analogues of tyrosine and lysine that can be incorporated into proteins in live cells were prepared in multi-gram quantities by a general two-step synthesis. These analogues consist of a caged lysine and a caged tyrosine, which can enable spatial and temporal control of protein activity by irradiation with UV light. Also, alkene-bearing lysines presenting different chain lengths have been synthesized and can participate in photoclick reactions as a new means to further functionalize a protein. The syntheses commence with a nucleophilic substitution reaction of the Boc-protected amino acids with the N-hydroxysuccinimidyl esters or chloroformates of the appropriate functional side chains. Finally, trifluoroacetic acid Boc-deprotection furnishes the desired unnatural amino acid.