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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
).Fig. 1.
Generic structure for α-vinyl amino acids.
