Pyruvic Acid → N-(1-Carboxyethyl)-L-alanyl-L-proline

Participants

Reaction Steps

A solution of L-alanyl-L-proline (372 mg) and pyruvic acid (881 mg) in water is adjusted to pH 7 and treated with 377 mg of sodium cyanoborohydride at room temperature until reaction is complete. The product is absorbed on strong acid ion-exchange resin and then eluted with 2% pyridine in water. Freeze drying gives 472 mg of N-(1-carboxyethyl)-L-alanyl-L-proline. Nmr and mass spectrogram are consistent with structure. The nmr spectrum shows multiplets centered at 4.5, 3.7, and 2.2 ppm, and a pair of doublets at 1.6 ppm.

Provenance & Evidence