title: Potent new leucine aminopeptidase inhibitor of novel structure synthesised by a modified Wadsworth-Emmons (Horner) Wittig procedure.
abstract: The use of a leucine-derived alpha-keto-beta-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.
authors.affiliation: Division of Biomedicinal Chemistry, School of Pharmacy, The Queen's University of Belfast, Medical Biology Centre, UK. brian.walker@qub.ac.uk
authors.forename: B
authors.initials: B
authors.lastname: Walker
authors.forename: P A
authors.initials: PA
authors.lastname: Darkins
authors.forename: M A
authors.initials: MA
authors.lastname: McKervey
authors.forename: H M
authors.initials: HM
authors.lastname: Moncrieff
authors.forename: J F
authors.initials: JF
authors.lastname: Lynas
mesh_terms: D002625:Chemistry, Organic / Q000379:methods; D006037:Glyoxal / Q000737:chemistry*; D007931:Leucyl Aminopeptidase / Q000037:antagonists & inhibitors*; D009682:Magnetic Resonance Spectroscopy; D011480:Protease Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology
chemical_list: D011480:Protease Inhibitors; D006037:Glyoxal; D007931:Leucyl Aminopeptidase