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Terpenes Alkaloids Pheromones Antibiotics

Introduction to Natural Products. Terpenes Alkaloids Pheromones Antibiotics. Terpenes. When we discuss the terpenes we are most interested in the carbon skeleton. Introduction to Natural Products. Isoprene. Introduction to Natural Products. Head. Isoprene. Tail. Head. Tail.

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Terpenes Alkaloids Pheromones Antibiotics

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  1. Introduction to Natural Products • Terpenes • Alkaloids • Pheromones • Antibiotics

  2. Terpenes • When we discuss the terpenes we are most interested in the carbon skeleton.

  3. Introduction to Natural Products Isoprene

  4. Introduction to Natural Products Head Isoprene Tail Head Tail

  5. Introduction to Natural Products Head Isoprene Tail Head Tail

  6. Terpene Classification • Class Name Isoprene Units Carbon Number

  7. Terpene Classification • Class Name Isoprene Units Carbon Number • Monoterpene 2 10

  8. Terpene Classification • Class Name Isoprene Units Carbon Number • Monoterpene 2 10 • Sesquiterpene 3 15

  9. Terpene Classification • Class Name Isoprene Units Carbon Number • Monoterpene 2 10 • Sesquiterpene 3 15 • Diterpene 4 20

  10. Terpene Classification • Class Name Isoprene Units Carbon Number • Monoterpene 2 10 • Sesquiterpene 3 15 • Diterpene 4 20 • Triterpene 6 30

  11. CH OH 2 -Terpinene a Monoterpene Examples O Myrcene Geraniol Cineole O O O OH Menthol Thujone Menthone Carvone

  12. Sesquiterpene Examples

  13. Representative Diterpenes

  14. Representative Triterpenes

  15. -Pinene a -Selinene b Isoprene Units in Terpenes O Limonene Camphor OH Guaiol

  16. -Pinene a -Selinene b Isoprene Units in Terpenes O Limonene Camphor OH Guaiol

  17. -Pinene a -Selinene b Isoprene Units in Terpenes O Limonene Camphor OH Guaiol

  18. -Pinene a -Selinene b Isoprene Units in Terpenes O Limonene Camphor OH Guaiol

  19. -Pinene a -Selinene b Isoprene Units in Terpenes O Limonene Camphor OH Guaiol

  20. Non-Isoprenoid Terpenes

  21. Alkaloids Nitrogen containing, basic natural products often have powerful biological activity alkaloids are not as conveniently organized by some common structural component.

  22. Examples of alkaloids

  23. Antiobiotics There are many classes of antibiotics; four are listed as major groups: b-lactams ( includes the penicillins); tetracyclines (tetracycline); macrolides (erythromycin) and peptides (gramacidin). For the purposes of this course, we will be primarily concerned with macrolide antibiotics and highly-oxygenated compounds.

  24. Practice Problem #1 • For each of the example terpenes given to you, find the isoprene units that are contained in the carbon skeleta.

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