| TOPICS | READINGS |
|---|---|
| Introduction and Peptide Biosynthesis | Dewick, chapter 7, pp. 421-454. Chatterjee, Champak, et al. "Biosynthesis and Mode of Action of Lantibiotics." Chem Rev 105 (2005): 633-683. Sieber, Stephan A., and Mohamed A. Marahiel. "Molecular Mechanisms Underlying Nonribosomal Peptide Synthesis: Approaches to New Antibiotics." Chem Rev 105 (2005): 715-738. |
| Polyketide Biosynthesis | Dewick, chapter 3, pp. 60-117. McDaniel, Robert, Mark Welch, and C. Ricard Hutchinson. "Genetic Approaches to Polyketide Antibiotics 1." Chem Rev 105 (2005): 543-558. Weissman, Kira J., et al. "The Molecular Basis of Celmer's Rules: The Stereochemistry of the Condensation Step in Chain Extension on the Erythromycin Polyketide Synthase." Biochemistry 36 (1997): 13849-13855. Shen, Ben. "Polyketide biosynthesis beyond the type I, II and III polyketide synthase paradigms." Current Opinion in Chemical Biology 7 (2003): 285-295. |
| Glycosylation and Halogenation | Dewick, chapter 8, pp. 465-485. |
| Aromatic Polyketide Biosynthesis | Shen, Ben. "Biosynthesis of Aromatic Polyketides." Topics in Current Chemistry 209 (2000): 1-51. |
| Saccharide Biosynthesis | He, Xuemei M., and Hung-wen Liu. "Formation Of Unusual Sugars: Mechanistic Studies and Biosynthetic Applications." Annu Rev Biochem 71 (2002): 701-54. Koeller, Kathryn M., and Chi-Huey Wong. Fig. Schemes 2 and 5 in "Synthesis of Complex Carbohydrates and Glycoconjugates: Enzyme-Based and Programmable One-Pot Strategies." Chem Rev 100 (2000): 4465-4494.  Walsh, Christopher. Enzymatic Reaction Mechanisms. San Francisco, CA: W.H. Freeman Company, 1978, pp. 778-781. ISBN: 9780716700708.He, Xuemei, Gautam Agnihotri, and Hung-wen Liu. Structures 3-6, Scheme 2, and Scheme 1 in "Novel Enzymatic Mechanisms in Carbohydrate Metabolism." Chem Rev 100 (2000): 4615-4662. He, Xuemei, and Hung-wen Liu. Schemes 5, 6, 7, 8, 9, 11, 14, 16, and 17 in "Formation Of Unusual Sugars: Mechanistic Studies and Biosynthetic Applications." Ann Rev Biochem 71 (2002): 701-754. Chen, Huawei, et al. Scheme 1 in "Deoxysugars in glycopeptide antibiotics: Enzymatic synthesis of TDP-L-epivancosamine in chloroeremomycin biosynthesis." PNAS 97 (2000): 11942-11947. |
| Shikimic Acid | Dewick, chapter 4, pp. 121-132, 142-144, and 149-157. Mann, John. "The shikimic acid pathway: biosynthesis of phenols, lignans, flavonoids, etc." In Chemical Aspects of Biosynthesis. New York, NY: Oxford University Press, 1995, pp. 53-7. ISBN: 9780198556763. Choroba, Oliver W., Dudley H. Williams, and Jonathan B. Spencer. "Biosynthesis of the Vancomycin Group of Antibiotics: Involvement of an Unusual Dioxygenase in the Pathway to (S)-4-Hydroxyphenylglycine." J Am Chem Soc 122 (2000): 5389-5390. Austin, Michael B., and Joseph P. Noel. "The chalcone synthase superfamily of type III polyketide synthases." Nat Prod Rep 20 (2003): 79-110. |
| Alkaloids | Dewick, chapter 6, pp. 291-337, 368-376, and 393-396. |
| Terpene Biosynthesis | Dewick, chapter 5, pp. 167-186, and 191-219. Davis, Edward M., and Rodney Croteau. "Cyclization Enzymes in the Biosynthesis of Monoterpenes, Sesquiterpenes, and Diterpenes." Topics in Current Chemistry 209 (2000): 53-95. Carey, Francis A., and Richard J. Sundberg. Advanced Organic Chemistry, Part A: Structure and Mechanisms. New York, NY: Springer-Verlag, 2004, pp. 312-9. ISBN: 9780306462436.Hayes, T., et al. "Feminization of male frogs in the wild." Nature 419 (2002): 895-6. Peters, Reuben J., et al. "Bifunctional Abietadiene Synthase: Mutual Structural Dependence of the Active Sites for Protonation-Initiated and Ionization-Initiated Cyclizations." Biochemistry 42 (2003): 2700-2707. Ye, Xudong, et al. "Engineering the Provitamin A (β-Carotene) Biosynthetic Pathway into (Carotenoid-Free) Rice Endosperm." Science 287 (2000): 304-5. Jennewein, Stefan, et al. "Random sequencing of an induced Taxus cell cDNA library for identification of clones involved in Taxol biosynthesis." PNAS 101 (2004): 9149-9154. Williams, David C., et al. "Intramolecular proton transfer in the cyclization of geranylgeranyl diphosphate to the taxadiene precursor of taxol catalyzed by recombinant taxadiene synthase." Chemistry & Biology 7 (2002): 969-977. |
Table of Contents
Study Materials
Readings
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Dewick readings are from the required textbook:
Dewick, Paul M. Medicinal Natural Products: A Biosynthetic Approach. 2nd ed. New York, NY: John Wiley & Sons, Inc., 2001. ISBN: 9780471496410 (paperback); ISBN: 9780471496403 (hardcover).