Zeitschrift für Chromatographie und Trenntechniken
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Enantio Separation of HMB (1-Hydroxy Methylthio Butanoic Acid) through Chymotrypsin Catalysed Peptide Synthesis and Chiral LC-MS Assessment

Srinivasan S*, Kapila S, Forciniti D and Nam P

Alpha hydroxy acids (AHAs) have received wide attention in cosmetic and animal-feed industries. Lactic acid, malic acid and the hydroxy analog of methionine (HMB) are important members of the AHA group. The chemically synthesized formulations of alpha hydroxy acids are a racemic mixture comprising of 50% L and 50% D forms. It is a well-documented fact that enantiomeric forms of chemicals can possess different activities. Enantio purity of chemicals is important in their use in pharmaceutical applications and it may play a significant role in nutritional and cosmetic applications as well. However, this role has not been fully documented because of the lack of enantio pure HMB and other AHAs. In this work, papain and chymotrypsin catalyzed peptide capping was evaluated for obtaining enantio pure alpha hydroxy acids. Chymotrypsin catalyzed peptide capping was found to be a very fast and efficient tool to obtain enantiopure HMB. The enantio purity of products was evaluated with Reverse Phase liquid Chromatography and Chiral Liquid Chromatography-Mass Spectrometry. The results indicate that enantio-purity of greater than 95% was obtained in less than ~30 minutes with chymotrypsin catalyzed capping HMB capping reaction.