Amino-acid conjugates of the hapten 2-phenyl-4-ethoxymethylene-5(4H)-oxazolone. Synthesis and confirmation of structure.
2-Phenyl-4-ethoxymethylene-5(4H)-oxazolone (PhOx = CHOEt) was reacted with methylamine, and 2-phenyloxazole-4-carboxylic acid was coupled with methylamine. The spectroscopic properties of the two products were compared in order to confirm that aminolysis of PhOx = CHOEt occurs by displacement of the ethoxy group to give 2-phenyl-4-(substituted-methylene)-5(4H)-oxazolones and not by attack at the oxazolone-carbonyl followed by rearrangement to give 2-phenyloxazole-4-carboxamides. Ten crystalline conjugates were prepared and characterized by reacting PhOx = CHOEt with an excess of unprotected di- and trifunctional amino acid anions followed by purification by washing them with hydrochloric acid.
Benoiton
N L
NL
Department of Biochemistry, University of Ottawa, Ontario, Canada.
Hudecz
F
F
Chen
F M
FM
D000596:Amino Acids / Q000737:chemistry*; D006241:Haptens / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D010081:Oxazolone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D010455:Peptides / Q000138:chemical synthesis
D000596:Amino Acids; D006241:Haptens; D010455:Peptides; D010081:Oxazolone