Abstract by Joseph Chanthakhoun
Chemistry and Biochemistry
Synthesis of Bulky Alpha,Beta-dehydroamino acids
Alpha,Beta-dehydroamino acids (dAAs) are dehydrated, planar analogs of amino acids shown to impart substantial proteolytic stability in peptides. Given this property, dAAs can be incorporated into peptide-based pharmaceutical drugs to potentially heighten their stability and potency. However, it is currently unknown which dAAs, whether small or bulky, are best for imparting proteolytic stability or the most efficient methods for synthesizing them. This study is a progress report on the synthesis of dehydrovaline and its precursors. By understanding the synthesis mechanisms of this dAA, methods for synthesizing other dAAs can be developed to test their incorporation into peptides.