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24 juillet 2023 - 14:12
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Medicinal Chemistry and Penicillin Total Synthesis: Crash Course Organic Chemistry #50
These days, we don't have to worry too much about meeting an early demise from ulcers, breaks in the stomach lining that could be fatal back in the early 1900s. This is because we have medicines to treat them, like proton pump inhibitors! In this final episode of Crash Course Organic Chemistry, we'll look at medicinal chemistry by breaking down how penicillin fights bacteria, how proteins are made both in the body and in the lab, and we'll finally finish our synthesis of penicillin V and complete our Mold Medicine Map! Hopefully this series has shown you the many ways organic chemistry is all around us and how it can help us to better understand ourselves, and improve our world!
Episode Sources:
Patrick, G. L. (2013). An introduction to medicinal chemistry. Oxford university press.
Vollmer, W., Blanot, D., & De Pedro, M. A. (2008). Peptidoglycan structure and architecture. FEMS microbiology reviews, 32(2), 149-167.
Sauvage, E., Duez, C., Herman, R., Kerff, F., Petrella, S., Anderson, J. W., ... & Charlier, P. (2007). Crystal structure of the Bacillus subtilis penicillin-binding protein 4a, and its complex with a peptidoglycan mimetic peptide. Journal of molecular biology, 371(2), 528-539.
PDB IDs (available at https://www.rcsb.org/):
• 5CXW
• 6TNA ( modified to show a bound amino acid)
Series Penicillin References:
Nicolaou, K. C., & Sorensen, E. J. (1996). Classics in total synthesis: targets, strategies, methods. John Wiley & Sons.
Sheehan, J. C. (1982). The enchanted ring: the untold story of penicillin.
Primary literature for Sheehan’s penicillin synthesis: Sheehan, J.C. & Izzo, P.T. J. Am. Chem. Soc. 1948, 70, 1985; Sheehan, J.C. & Izzo, P.T. J. Am. Chem. Soc. 1949, 71, 4059; Sheehan, J.C. & Bose A.K. J. Am. Chem. Soc. 1950, 72, 5158; Sheehan, J.C., Buhle, E.L, Corey E.J., Laubach, G.D. & Ryan J.J. J. Am. Chem. Soc. 1950, 72, 3828; Sheehan, J.C. & Laubach, G.D. J. Am. Chem. Soc. 1951, 73, 4376; Sheehan, J.C. & Hoff, D.R. J. Am. Chem. Soc. 1957, 79, 237; Sheehan, J.C. & Corey E.J. J. Am. Chem. Soc. 1951, 73, 4756
Series Sources:
Brown, W. H., Iverson, B. L., Ansyln, E. V., Foote, C., Organic Chemistry; 8th ed.; Cengage Learning, Boston, 2018.
Bruice, P. Y., Organic Chemistry, 7th ed.; Pearson Education, Inc., United States, 2014.
Clayden, J., Greeves, N., Warren., S., Organic Chemistry, 2nd ed.; Oxford University Press, New York, 2012.
Jones Jr., M.; Fleming, S. A., Organic Chemistry, 5th ed.; W. W. Norton & Company, New York, 2014.
Klein., D., Organic Chemistry; 1st ed.; John Wiley & Sons, United States, 2012.
Louden M., Organic Chemistry; 5th ed.; Roberts and Company Publishers, Colorado, 2009.
McMurry, J., Organic Chemistry, 9th ed.; Cengage Learning, Boston, 2016.
Smith, J. G., Organic chemistry; 6th ed.; McGraw-Hill Education, New York, 2020.
Wade., L. G., Organic Chemistry; 8th ed.; Pearson Education, Inc., United States, 2013.
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