While life on earth is exclusively based on L-amino acids and D-sugars, it has recently been found that D-amino acid-containing molecules do exhibit a variety of important bioactivities. Natural antibiotics involving D-amino acid units have been isolated from bacteria and many reports have revealed the participation of D-amino acids in certain biological processes and cell functions. D-amino acids possess “unnatural” chiral centers that make them attractive as building blocks for the synthesis of bioactive compounds. Incorporation of D-amino acids into peptide chains and cyclic peptides can severely affect their interactions with biological targets and their slower degradation compared to the corresponding L isomers can be of great use in therapeutics.<br/><br/>D-amino acids are most commonly obtained via racemization of <i>natural</i> L-amino acids followed by chiral separation; however, production of commercially viable amounts is still complicated and expensive. In the specific case of vinylglycine, racemization is not a viable option due to isomerization. This project aims at developing a unique, inexpensive approach to synthesizing D-vinylglycine from L-serine as starting material. Given the exploitable reactivity of vinylglycine, ready synthetic access to the D enantiomer will provide the material needed to study its incorporation into peptides for late-stage site-specific structural modification and the synthesis of complex D-branched amino acid-like moieties.

Studies toward a convenient and inexpensive synthesis of D-vinylglycine

250th National Meeting (2015)

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