Master of Chemical and Life Sciences Program College of Computer, Mathematical, and Natural Sciences

CLFS 610: Natural Products Chemistry

Syllabus

Instructor Bruce Jarvis

Natural products are relatively small molecules, produced mainly by plants and microorganisms, that have a long history of uses (and misuses) by people, e. g. poisons, antibiotics, perfumes, malodorants, cosmetics, dietary supplements, etc. This course will focus on the medical and nutritional applications of natural products and be organized on the basis of the biosynthetic pathways that lead to these natural organic compounds. The course is meant to complement other courses in the curriculum, principally Chemical Ecology and Pharmaceutical Chemistry.

Unit 1: Basics of Organic Chemistry: structure drawing, functional groups, shapes, conformations, polarity/non‐polarity 1. Objectives 2. Natural Products 3. A Brief Review of Drawing Organic Chemical Structures ! 4. The Functional Group 5. Molecular Shapes and Polar/non‐polar Properties 6. Stereochemistry in Nature 7. The Techniques of Natural Product Chemical Research 8. Synthesis: An Example 9. Assignments & Exercises

Unit 2: Basics of Metabolism (primary & secondary), Reactive Intermediates in Biosynthesis, Pharmacology 1. Introduction: Biochemistry & Reactive Intermediates 2. MetBuildBlock.html 3. Metabolism: Energetics 4. Metabolism: The Catalysts I 5. Metabolism: The Catalysts II 6. Reactive Intermediates and Mechanisms in Biosynthesis 7. Carbocations 8. Carbanions 9. Radicals 10. Basic Mechanisms: Amino Acids & Proteins 11. Amino Acids & Peptides 12. Assignments & Exercises

CLFS 610: Course Syllabus, p. 1 Unit 3: The Acetate Pathways, Fatty Acid & Polyketide Biosyntheses: fats & oils, prostaglandins, phenolics & anthraquinones, macrolide antibiotics, genetic manipulations of the polyketide genetic "machinery" 1. Lipids 2. The Unsaturated Fatty Acids 3. Unusual Fatty Acids 4. Polyketides. 5. Mixed Biosynthetic Pathways 6. Antibiotics 7. Assignments & Exercises

Unit 4: Aromatic Amino Acids & Phenyl Propanoids: lignans, coumarins, flavanoids, & terpenoid quinones (e. g. vitamins E & K) 1. Introduction: The Shikimate Pathway 2. The Sulfa drugs 3. Siderophores 4. Cinnamic Acid derivatives 5. Coumarins 6. Lignans‐Lignins 7. The Flavonoids 8. The Condensed Tannins 9. Assignments & Exercises

Unit 5: The Terpenes: volatile oils, taxol, ginkolides, mycotoxins, and steroids 1. Introduction to Terpenes 2. Biosynthesis 3. The Two Pathways 4. Monoterpenes 5. Sesquiterpenes 6. Terpenes4.htm 7. Terpenes4.htm 8. The Triterpenoid Steroids 9. The Terpenes 10. Assignments & Exercises

Unit 6: Alkaloids: Drugs (cocaine, opiates, quinine, vincristine, curare, mescaline, etc.) and toxins (nicotine, lupinines, strychnine, tetrodotoxin, etc.) 1. Introduction 2. Simple Alkaloids I: Pyrrole Derivatives 3. Simple Alkaloids II: Piperidine Derivatives 4. Aromatic Alkaloids I: Simple Derivatives 5. Aromatic Alkaloids II: More Complex Derivatives 6. The Indole Alkaloids 7. Miscellaneous Alkaloids with Interesting Bioactivities 8. Assignments & Exercises

CLFS 610: Course Syllabus, p. 2

Unit 7: Carbohydrate and Amino Acid Derivatives: peptide hormones & venoms, antibiotics (e. g. penicillins), amino sugars 1. Polypeptides and Related Natural Products 2. Ribosomal Polypeptide Synthesis 3. .Post‐translational Modifications 4. Non‐Ribosomal Polypeptide Synthesis 5. The Polypeptide Antibiotics 6. The Beta‐Lactam Antibiotics I: The Penicillins 7. The Beta‐Lactam Antibiotics II: Other Beta‐Lactams 8. Concluding Remarks 9. Assignments & Exercises

CLFS 610: Course Syllabus, p. 3