Chapter 8: Polyketides and Terpenes Reading Guide

Guiding Questions: ​Answer these questions as you read through Chapter 1. Some will require
you to draw on previous knowledge presented earlier in the chapter, and some ask that you
dissect what you are learning. The overall goal is to guide your understanding of the big ideas.

Learning Objectives
● Distinguish between the chemical mechanisms for iterative carbon-carbon bond formation in
polyketide biosynthesis and terpene biosynthesis.
● Recognize the limited structural range of human polyketides and human terpenes.
● Appreciate the unlimited structural range of polyketides and terpenes found in lower
organisms and plants.
● Describe the origin and effects of eicosanoid and sphingoid signaling molecules.
● Understand the origin of diversity in polyketide metabolism from lower organisms.
● Explain the structure and reactivity of nonclassical carbocations.
● Describe how cationic cyclizations and rearrangements amplify the diversity of terpene
natural products.

Introductory Section - Section 8.2

1. What is a polyketide? What building blocks make up polyketides?

2. What is a terpene? What building blocks make up terpenes?

3. What are primary metabolites? What are secondary metabolites?

4. What chemical reaction is involved in the formation of polyketides? Draw an example.

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5. What is coenzyme A? What is its primary function?

6. On average, how many protein domains comprise a fatty acid synthase? Draw an example of
a fatty acid synthase.

7. What is the primary function of the following proteins:

● acyl carrier protein

● transacylase

● ketosynthase

● ketoreductase

● dehydratase

● thioesterase

Sections 8.3 - 8.5

8. What is the basic structure of a phospholipid (i.e. what part is polar, what part is
hydrophobic)? What is the basic structure of a sphingolipid? What is the major difference
between the two?

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9. What is a lipid raft?

10. What parts of phospholipids and sphingolipids are exposed to the extracellular and
intracellular space? What parts are not?

11. What derivatives are important in intracellular signalling? What is intracellular signalling?
Look it up if you are unsure.

12. What is a fatty acid?

13. What chemical reaction facilitates the synthesis of biofuels?

14. Why are polyketide natural products so diverse?

15. How are type I polyketide synthases modular? Draw an example. What does modular mean
in this case?

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Sections 8.6 - 8.8

16. What are some examples of human terpenes?

17. What base units undergo cationic additions to form linear chains? Draw the base unit.

18. What is a prenyl subunit? Draw an example.

19.What are prenylated quinones? What purpose do they serve in redox chemistry?

20. What does protein prenylation do?

21. Give at least 10 examples of human terpenes.

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22. Give at least 10 examples of non-human terpenes. Where are many terpenes found?

23. What purpose does the 2-norbornyl cation serve?

24. What are terpene cylases? What are terpene synthases?