Synthesis of a reaction intermediate analogue of biotin-dependent carboxylases via a selective derivatization of biotin.
[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.
Amspacher
D R
DR
Department of Chemistry, Louisiana State University, Baton Rouge 70803, USA.
Blanchard
C Z
CZ
Fronczek
F R
FR
Saraiva
M C
MC
Waldrop
G L
GL
Strongin
R M
RM
D001360:Avidin / Q000737:chemistry; D001710:Biotin / Q000138:chemical synthesis / Q000737:chemistry*; D019731:Carbon-Nitrogen Ligases / Q000037:antagonists & inhibitors / Q000737:chemistry*; D007700:Kinetics
D001360:Avidin; D001710:Biotin; D019731:Carbon-Nitrogen Ligases; C019791:biotin carboxylase