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Violacein is an intensely purple microbial pigment with an arsenal of biological activity. A structural analog to the better-known bis-indole alkaloids staurosporine and rebeccamycin, violacein has been touted as an antimicrobial and anticancer therapeutic. It is most frequently obtained as a biosynthetic secondary metabolite from bacterial cell cultures. However, we have developed an efficient, environmentally benign methodology for synthesizing the natural product via a 3-component condensation in polyethylene glycol. Violacein, along with a series of analogs have been prepared in our laboratory. The deoxyviolacein analog has been investigated for its effects against cancer cell migration in HeLa. This initial screening has served as the impetus to study deoxyviolacein’s specific interactions in cancer cells via proteomics. In this project, the synthesis of the deoxyviolacein scaffold for solid support is designed, in preparation for SILAC (Stable Isotope Labeling by Amino acids in Cell culture) analysis. The synthesis requires preparation of 5-hydroxymethyl-1H-indole, reported here. The main objective of this project is to design and synthesize a functional analog that can be used to determine the protein interactions responsible for the biological activity of violacein.
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Oppong-Holmes, Awura Ama A., "Synthesis of Violacein for Stable Isotopic Labeling by Amino Acids in Cell Culture" (2018). Senior Projects Spring 2018. 27.