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Published on: January 19, 2016
Chemical reactivity of the tryptophan/acetone/DMSO triad system and its potential applications in nanomaterial
Chun-Yi Huang1, Hsiao-Wei Liao1, Teh-Min Hu1
1Department of Pharmacy, College of Pharmaceutical Sciences, National Yang Ming Chiao Tung University 112304 Taipei Taiwan tehmin@nycu.edu.tw.
Abstract:
Previously, we reported a novel browning reaction of amino acids and proteins in an organic solvent mixture composed of dimethyl sulfoxide (DMSO) and acetone. The reaction proceeds under surprisingly mild conditions, requiring no heating or additional reactants or catalysts. This present study aimed to investigate the chemical reactivity of the triad reaction system of l-tryptophan/aectone/DMSO. We demonstrated that, in DMSO, l-tryptophan initially catalyzed the self-aldol condensation of acetone, resulting in the formation of mesityl oxide (MO). Furthermore, we showed that the three-component system evolved into a diverse chemical space, producing various indole derivatives with aldehyde or ketone functional groups that exhibited self-assembling and nanoparticle-forming capabilities. We highlight the potential applications in nanomaterial synthesis.
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