Date of Award

Spring 5-19-2018

Degree Type

Thesis

Degree Name

MS Chemistry

Department

Chemistry and Biochemistry

Advisor

Joseph J. Badillo, Ph.D.

Committee Member

David Sabatino, Ph.D.

Committee Member

Cecilia Marzabadi, Ph.D.

Keywords

Bioconjugation, organocatalyst, Henry reaction, protein modification, site-selective.

Abstract

In this research, peptides and protein containing serine on the N-terminus underwent site-selective modification following organocatalyzed bioconjugation that offered an additional functional group. It was shown that transforming the N-terminus serine to an aldehyde allowed site-specific bioconjugation to occur by utilizing the well-known Henry reaction. This method also grants a safer pathway for bioconjugation utilizing “green-chemistry” and biocompatible conditions. Amino acids and amino acid derived organocatalysts were utilized in the Henry reaction resulting in yields of up to 86 % conversion. Promising preliminary results were achieved in this research using peptides and myoglobin as the bioconjugation targets. Further investigation to be performed includes the analysis of the final product, as well as, applying this methodology to a number of other proteins.

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