Document Type
Article
Department/Program
Chemistry
Journal Title
Bioconjugate Chemistry
Pub Date
2015
Volume
26
Issue
9
First Page
1884
Abstract
The utilization of unnatural amino acids (UAAs) in bioconjugations is ideal due to their ability to confer a degree of bioorthogonality and specificity. In order to elucidate optimal conditions for the preparation of bioconjugates with UAAs, we synthesized 9 UAAs with variable methylene tethers (2-4) and either an azide, alkyne, or halide functional group. All 9 UAAs were then incorporated into green fluorescent protein (GFP) using a promiscuous aminoacyl-tRNA synthetase. The different bioconjugations were then analyzed for optimal tether length via reaction with either a fluorophore or a derivatized resin. Interestingly, the optimal tether length was found to be dependent on the type of reaction. Overall, these findings provide a better understanding of various parameters that can be optimized for the efficient preparation of bioconjugates.
Recommended Citation
Maza, Johnathan C.; McKenna, Jaclyn R.; Raliski, Benjamin K.; Freedman, Matthew T.; and Young, Douglas D., Synthesis and Incorporation of Unnatural Amino Acids To Probe and Optimize Protein Bioconjugations (2015). Bioconjugate Chemistry, 26(9), 1884-1889.
10.1021/acs.bioconjchem.5b00424
DOI
10.1021/acs.bioconjchem.5b00424
