Advanced Bioorganic Chemistry


Unit code: CHEM41412
Credit Rating: 10
Unit level: Level 4
Teaching period(s): Semester 2
Offered by School of Chemistry
Available as a free choice unit?: N

Requisites

None

Aims

  

  • The expansion and development of the student’s knowledge of the fundamentals of advanced bioorganic chemistry.
  • Provide an understanding of the organic chemistry that underlies the biosynthetic pathways to the major groups of secondary metabolites (natural products), including enzyme mechanisms and methods of biosynthetic engineering (combinatorial biosynthesis).
  • Develop ideas of biomimetic chemistry, including the exploitation of predisposed chemical reactions in the total synthesis of natural products.
  • Explore the application of enzymes and whole cells as biocatalysts for organic synthesis. Identify specific classes of biocatalysts that can be used for the preparation of chiral building blocks for pharmaceutical, agrochemicals and fine chemical production. Study methods for enzyme improvement via directed evolution and protein engineering.

Overview

Biosynthesis & Biosynthetic Engineering (J Micklefield, 8 lectures)

  • Fatty acids & lipids
  • Polyketides & nonribosomal peptides
  • Biosynthetic engineering and combinatorial biosynthesis strategies

Metabolic Processes & Biomimetic Synthesis (R Whitehead, 8 lectures)

  • Examples of metabolic transformations
  • Examples of biomimetic (predisposed) synthesis.

Biocatalysis (A Munro & N Weise, 8 lectures)

  • Fundamental of biocatalysis including different enzyme classes
  • Examples of biotransformations useful for synthesis, e.g. hydrolytic, redox, C-X bond formation
  • Applications of biocatalysts in the synthesis of enantiomerically pure building blocks with emphasis on applications in industry
  • Directed evolution of enzymes.

Teaching and learning methods

  • Lectures (24), including worked examples
  • Problems

Learning outcomes

 Students successfully completing this unit should:

  • Understand the organic chemistry of biosynthetic pathways, metabolic transformations and biotransformations.
  • Apply this knowledge in the biosynthetic engineering (or combinatorial biosynthesis) of ‘unnatural’ natural products.
  • Apply the knowledge of metabolic transformations and predisposed biomimetic reactions in the synthesis of natural products.
  • Apply the knowledge of enzyme-catalysed reactions in the development of chemical processes employing biocatalysts.
  • Understand the principles of directed evolution of enzymes and how this technique can be used to improve the properties of biocatalysts
  • Enhance their transferable skills in the areas of problem solving and analysis

Transferable skills and personal qualities

Enhance their transferable skills in the areas of problem solving and analysis

Assessment methods

  • Written exam - 100%

Recommended reading

 

  • The Organic Chemistry of Biological Pathways McMurry & Begley (Roberts & company)
  • Biochemistry Third Edition, Voet & Voet (Wiley)
  • Biochemistry Third Edition, Stryer, L. (Freeman)
  • Chemical aspects of biosynthesis John Mann (Oxford Chemistry Primers)
  • Kurt Faber, Biotransformations in Organic Chemistry, 5th Edition, Springer

Feedback methods

 Students will work through the problem sheets issued during lectures (posted on blackboard) and submit for feedback

Study hours

  • Assessment written exam - 2 hours
  • Lectures - 24 hours
  • Independent study hours - 74 hours

Teaching staff

Jason Micklefield - Unit coordinator

Roger Whitehead - Unit coordinator

Andrew Munro - Unit coordinator

Nicholas Weise - Unit coordinator

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