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Secondary Metabolites

Module description

In this module, you will learn about how microorganisms make structurally complex metabolites, such as nicotine, the antibacterial drug erythromycin and cholesterol, from simple basic building blocks. We will explore the pathways that are used to build up these molecules and the enzymes that catalyse the reactions. We will also discuss the shikimic acid pathway.  The structure and chemistry of amino acids and monosaccharides will also be examined and you will gain an understanding of their typical reactions and how they are used in synthesis.

Module aims - intentions of the module

This module aims to study the applications of organic compounds in the natural world with particular reference to biological systems. It further aims to rationalise the properties and reactivity of the principal classes of natural products and to demonstrate the fundamental chemistry behind biochemical reactions in biosynthetic pathways.

Intended Learning Outcomes (ILOs)

ILO: Module-specific skills

On successfully completing the module you will be able to...

• 1. Recognise and draw complex natural products and biomolecules in three dimensions
• 2. Summarise and critically evaluate the organic aspects of chemical processes important in biology
• 3. Illustrate and critically discuss the structure and function of important biomolecules
• 4. Discuss the chemical reactivity and physical properties of important biomolecules

ILO: Discipline-specific skills

On successfully completing the module you will be able to...

• 5. Evaluate in detail approaches to our understanding of chemical biology with reference to primary literature, reviews and research articles
• 6. Analyse in detail essential facts and theory in a sub-discipline of the biosciences
• 7. Analyse and evaluate independently a range of research-informed literature and synthesise research-informed examples from the literature into written work
• 8. With limited guidance, deploy established techniques of analysis and enquiry within the biosciences

ILO: Personal and key skills

On successfully completing the module you will be able to...

• 9. Communicate effectively arguments, evidence and conclusions using written and oral means in a manner appropriate to the intended audience
• 10. Devise and sustain, with little guidance, a logical and reasoned argument with sound, convincing conclusions
• 11. Analyse and evaluate appropriate data with very limited guidance

Syllabus plan

Interaction of functional groups to produce molecules with unusual reactivity is exemplified by the polyketide-derived metabolites, the amino acids (acid-base properties, peptides and hormones), the carbohydrates (acetals, hemi-acetals and mutarotation, stereochemistry both configurational and conformational), certain heterocyclic bases, terpenes and organyl phosphates, shikimic-acid derived metabolites.

Description of natural product biosynthetic pathways based on acetate, amino acids and mevalonate and how they are investigated using labelled compounds

Comparison of biochemical reactions with the basic organic chemistry covered in previous modules.

Learning activities and teaching methods (given in hours of study time)

Details of learning activities and teaching methods

Formative assessment

Summative assessment (% of credit)

Details of summative assessment

Details of re-assessment (where required by referral or deferral)

Re-assessment notes

Deferral – if you miss an assessment for certificated reasons that are approved by the Mitigation Committee, you will normally be either deferred in the assessment or an extension may be granted. If deferred, the format and timing of the re-assessment for each of the summative assessments is detailed in the table above ('Details of re-assessment'). The mark given for a deferred assessment will not be capped and will be treated as it would be if it were your first attempt at the assessment.

Referral - if you have failed the module (i.e. a final overall module mark of less than 40%) and the module cannot be condoned, you will be required to complete a re-assessment for each of the failed components on the module. The format and timing of the re-assessment for each of the summative assessments is detailed in the table above ('Details of re-assessment'). If you pass the module following re-assessment, your module mark will be capped at 40%.

Indicative learning resources - Basic reading

• Mann J., Chemical Aspects of Biosynthesis, Oxford Primer, Oxford University Press, 1994, ISBN 0-19- 855676-4
• Dewick, PM, Medicinal Natural Products – A Biosynthetic Approach, Wiley-Blackwell, 2009, ISBN 0470741678
• J. H. Jones, Amino acids and Peptide Synthesis, Oxford Primer, Oxford University Press, 2002 ISBN 0-19-925738-8
• B. G. Davis and A. J. Fairbanks, Carbohydrate Chemistry, Oxford Primer, Oxford University Press, 2002 ISBN 0-19-855833-3

Indicative learning resources - Web based and electronic resources

• ELE page: https://vle.exeter.ac.uk/course/view.php?id=10233

Key words search

Microorganisms, amino acids, monosaccharides, biosynthesis, secondary metabolism, polyketides, terpenes, shikimate, alkaloids