The IUPUI spring 2013 Distributed Drug Discovery (D3) undergraduate laboratory program combining organic chemistry and microbiology will be discussed. To put the project in context, at the beginning of the semester, a 20-minute video describing D3 was presented to our organic laboratory students. This was followed by internet and computational exercises to assist students in their selection of the six target molecules they would synthesize. In mid-semester, prior to the laboratory, two additional 20-minute videos were presented: (a) development of this laboratory research project with the overall 5-step synthesis, and (b) mechanism of the alkylation reaction. The student syntheses involved preparation of three unnatural racemic amino acids A  and three N-acylated derivatives of the same amino acids B  from a resin-bound derivative of the simplest amino acid, glycine. This included an alkylation reaction to attach R1 (from R1X) and an N-acylation reaction to add R2CO (from R2CO2H). The racemic derivatives A  were then screened for activity in a biofilm formation assay by microbiology undergraduates. Bacillus subtilis or Pseudomonas aeruginosa were grown in the presence of the racemic derivatives to determine their effect on bacterial biofilm development. Derivatives with inhibitory effects may be candidates for drug leads to target biofilm-associated diseases. This work provides the first example of D3-linked interdisciplinary undergraduate student computational analysis, synthesis, and biological evaluation.

Distributed drug discovery (D3): Contextualized educational laboratory program in chemistry and biology toward inhibiting biofilm formation related to cystic fibrosis

246th National Meeting (2013)

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