Arginine-based Heterocyclic Amine

Ryan Hayes (Chemistry)

Synthesis and Separation of an Arginine-based Heterocyclic Amine

Heterocyclic Amines (HCAs) are formed through an unknown mechanism which combines creatine with various amino acids to form cyclic nitrogen structures with mutagenic properties.  Substantial research has been done on HCA formation in meat products where creatine is present.  It has been speculated in previous experiments as a result of analyzing by-products, but never experimentally investigated, that arginine can substitute for creatine and form HCAs in foods lacking animal tissue.  Arginine is a prominent amino acid found in many soy-based products which leads to speculation that over-cooked soy and other plant-based products could contain HCAs.  For our experiments we heated compounds containing creatine along with other essential compounds present during the reaction such as L-phenylalanine, water, and glucose to serve as a control mechanism  for the production of PhIP, a HCA.  We contrasted these results with identical tests with the only exception being the replacement of creatine with arginine.  Both experiments were compared to an HPLC retention time and spectral absorption graph of pure PhIP.  Our experiments strongly suggest it is possible to form PhIP as well as a new arginine-based HCA, that is very similar in structure to PhIP.  This research will focus on creating larger quantities of these materials for subsequent confirmation of structure and toxicity.

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