N-trifluoroacetyl-β-alanine in the synthesis of carnosine

Abstract

Conditions have been developed for the synthesis of N-trifluoroacetyl- β-alanine, N-tifluoroacetyl-β-alanyl chloride, and N-trifluoroacetyl-β-alanine 4-nitrophenyl ester. These compounds reacted with histidine methyl ester or sodium salt to give N-trifluoroacetyl-β- alanyl-l-histidine methyl ester CF3CONHCH2CH 2•CONHCH(CH2C3H3N 2)COOCH3 and N-trifluoroacetyl-β-alanyl-l-histidine CF3CONHCH2CH2CONHCH•(CH2C 3H3N2)COOH. Their hydrolysis with a solution of sodium hydroxide in aqueous ethanol, followed by acidification with trifluoroacetic acid, led to the formation of β-alanyl-l-histidine (l-carnosine). © 2007 Pleiades Publishing, Ltd.