The unusual amino acid vinylglycine and a number of related compounds have been studied throughout the years for their involvement in certain biological processes and special reactivity. Given the presence of an alkene moiety, the structure of vinylglycine could be manipulated through a variety of chemical reactions, leading to larger and more valuable amino acid-like structures. Exploiting late-stage transformations on vinylglycine-containing peptide-like molecules could be of great use in the medicinal field. <br/>   While the preparation of vinylglycine has been extensively investigated in the past, its production is still problematical due to its sensitivity to racemization and isomerization, which renders key steps irreproducible during its synthesis. This project aims at developing an inexpensive approach to synthesize L- and D-vinylglycine derivatives as single enantiomers, using D- and L-serine respectively as starting materials. Additionally, we expect to find a means to protect this structure from racemization and isomerization via an appropriate derivatization. Our progress in these endeavors will be presented.

Preparation of L- and D-vinylglycine-based building blocks for the synthesis of medically relevant complex molecules

254th National Meeting (2017)

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