1. Academic Validation
  2. Synthesis and Incorporation of Unnatural Amino Acids To Probe and Optimize Protein Bioconjugations

Synthesis and Incorporation of Unnatural Amino Acids To Probe and Optimize Protein Bioconjugations

  • Bioconjug Chem. 2015 Sep 16;26(9):1884-9. doi: 10.1021/acs.bioconjchem.5b00424.
Johnathan C Maza 1 Jaclyn R McKenna 1 Benjamin K Raliski 1 Matthew T Freedman 1 Douglas D Young 1
Affiliations

Affiliation

  • 1 Department of Chemistry, College of William & Mary P.O. Box 8795, Williamsburg, Virginia 23187, United States.
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.

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