Potent new leucine aminopeptidase inhibitor of novel structure synthesised by a modified Wadsworth–Emmons (Horner) Wittig procedure

The use of a leucine-derived α-keto-β-aldehyde (glyoxal) as a substrate in the Horner–Emmons (Wadsworth) Wittig reaction has enabled the synthesis of (Z)-7-methyl-5(S)-amino-4-oxo-methyl-oct-2-eneoate. This novel compound is a potent inhibitor (Ki=76 nM) of leucine aminopeptidase and provides an interesting new template for the development of metallopeptidase inhibitors.