Abstract
This chapter presents procedures for the synthesis of α-vinyl amino acids, in which the usual α-proton is replaced by an unsubstituted vinyl group (Fig. 1). The parent member of this family, α-vinylglycine (R≠H), is a natural product (1,2) and acts as a suicide substrate for a number of PLP-dependent enzymes (4–9). Higher members of this family (R≠H) have also been synthesized (10–12). Several including α-vinyl-m-tyrosine (13–15), α-vinyl-DOPA (13–15), α-vinylglutamate (16), α-vinylornithine (17), α-vinyllysine (18), and α-vinylarginine (18) are Trojan horse inhibitors of their cognate amino acid decarboxylases (AADCs). Such (appropriately labeled) AADC inhibitors may also have potential as reagents for positron emission tomography (19).
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References
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Berkowitz, D.B., McFadden, J.M., Smith, M.K., Pedersen, M.L. (1999). Synthesis of α-Vinyl Amino Acids. In: Kazmierski, W.M. (eds) Peptidomimetics Protocols. Methods in Molecular Medicine™, vol 23. Humana Press. https://doi.org/10.1385/0-89603-517-4:467
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DOI: https://doi.org/10.1385/0-89603-517-4:467
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