title: Synthesis of a reaction intermediate analogue of biotin-dependent carboxylases via a selective derivatization of biotin.
abstract: [formula: see text] An efficient and practical synthesis of 1, a unique reaction intermediate analogue of biotin-dependent carboxylases, is described. The synthesis features a selective acylation of the 1'-N of biotin. Target 1 inhibits the activity of the biotin carboxylase component of acetyl CoA carboxylase. It is the first known biotin-derived inhibitor of biotin carboxylase and should promote new kinetic and structural studies of the biotin-dependent carboxylases.
authors.affiliation: Department of Chemistry, Louisiana State University, Baton Rouge 70803, USA.
authors.forename: D R
authors.initials: DR
authors.lastname: Amspacher
authors.forename: C Z
authors.initials: CZ
authors.lastname: Blanchard
authors.forename: F R
authors.initials: FR
authors.lastname: Fronczek
authors.forename: M C
authors.initials: MC
authors.lastname: Saraiva
authors.forename: G L
authors.initials: GL
authors.lastname: Waldrop
authors.forename: R M
authors.initials: RM
authors.lastname: Strongin
mesh_terms: D001360:Avidin / Q000737:chemistry; D001710:Biotin / Q000138:chemical synthesis / Q000737:chemistry*; D019731:Carbon-Nitrogen Ligases / Q000037:antagonists & inhibitors / Q000737:chemistry*; D007700:Kinetics
chemical_list: D001360:Avidin; D001710:Biotin; D019731:Carbon-Nitrogen Ligases; C019791:biotin carboxylase