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Chemical synthesis: Chemical synthesis, the construction of complex chemical compounds from simpler ones
Vanderbilt Institute of Chemical Biology
Staphylococcus aureus is a leading cause of hospital-acquired infections in the USA and is a major health concern as methicillin-resistant S. aureus and other antibiotic-resistant strains are common. Compounds that inhibit the S. aureus sortase (SrtA) cysteine transpeptidase may function as potent anti-infective agents as this enzyme attaches virulence factors to the bacterial cell wall. While a variety of SrtA inhibitors have been discovered, the vast majority of these small molecules have not been optimized using structure-based approaches. Here we have used NMR spectroscopy to determine the molecular basis through which pyridazinone-based small molecules inhibit SrtA. These inhibitors covalently modify the active cysteine thiol and partially mimic the natural substrate of SrtA by inducing the closure of an active site loop. Computational and synthetic chemistry methods led to second-generation analogues that are ~70-fold more potent than the lead molecule. These optimized molecules exhibit broad-spectrum activity against other types of class A sortases, have reduced cytotoxicity, and impair SrtA-mediated protein display on S. aureus cell surface. Our work shows that pyridazinone analogues are attractive candidates for further development into anti-infective agents, and highlights the utility of employing NMR spectroscopy and solubility-optimized small molecules in structure-based drug discovery.
(Conjoined with Chem 154; formerly Chem 247.) A qualitative approach to the mechanisms of various organic reactions; substitutions, additions, eliminations, condensations, rearrangements, oxidations, reductions, free-radical reactions, and photochemistry. Includes considerations of molecular structure and reactivity, synthetic methods, spectroscopic tools, and stereochemistry. The topics emphasized will vary from year to year. This is the first quarter of the advanced organic chemistry sequence. Chem 254 students will be required to complete an additional paper and/or exam beyond that expected of students in Chem 154. Prerequisites: Chem 140C or 140CH (154), or graduate standing (254).
Elsevier Current Opinion - Current Opinion in Chemical Biology
Our vision is to approach the whole area of chemical synthesis as a group rather than as individuals. By bringing together inorganic, organic and physical chemists, we break down traditional barriers, providing a more holistic experience for our postgraduates.
(Conjoined with Chem 157.) A comprehensive survey of modern bioorganic and natural products chemistry. Topics include biosynthesis of natural products, molecular recognition, and small molecule-biomolecule interactions. Chem 257 students will be required to complete additional course work beyond that expected of students in Chem 157. Prerequisites: Chem 140C or 140CH (157), or graduate standing (257).
Current Opinion in Chemical Biology
I was unsure of the type of synthetic chemistry PhD project I wanted to carry out. I liked the idea of being able to try three different lab environments before choosing.
ACS Chemical Biology (ACS Publications)
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Our vision is to approach the whole area of chemical synthesis as a group rather than as individuals
Chemical Biology - Duke University
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Probing the Anti-cancer Mechanism of (-)-Ainsliatrimer A through Diverted Total Synthesis and Bioorthogonal Ligation
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