P-Azidophenacyl bromide, a versatile photolabile bifunctional reagent. Reaction with glyceraldehyde-3-phosphate dehydrogenase.
The synthesis of the photochemically labile bifunctional reagent p-azidophenacyl bromide (1) is described. This compound may be covalently attached to a known site of an enzyme or other macromolecule by nucleophilic displacement at the alpha-bromo ketone moiety. Subsequent irradiation of the bound reagent gives a nitrene which may insert into a second portion of the enzyme forming a cross-link. Regeant 1 proved to be an excellent inhibitor of rabbit muscle glyceraldehyde-3-phosphate dehydrogenase.
D000098:Acetophenones / Q000138:chemical synthesis / Q000494:pharmacology* / Q000528:radiation effects; D000818:Animals; D001386:Azides / Q000138:chemical synthesis / Q000494:pharmacology / Q000528:radiation effects; D001665:Binding Sites; D004355:Drug Stability; D005987:Glyceraldehyde-3-Phosphate Dehydrogenases / Q000037:antagonists & inhibitors* / Q000528:radiation effects; D009132:Muscles / Q000201:enzymology; D010782:Photolysis; D011485:Protein Binding; D011817:Rabbits; D011830:Radiation Effects; D014466:Ultraviolet Rays
D000098:Acetophenones; D001386:Azides; D005987:Glyceraldehyde-3-Phosphate Dehydrogenases; C011171:4-azidophenacyl bromide