Module Details
The information contained in this module specification was correct at the time of publication but may be subject to change, either during the session because of unforeseen circumstances, or following review of the module at the end of the session. Queries about the module should be directed to the member of staff with responsibility for the module.
Title NATURAL PRODUCT CHEMISTRY
Code CHEM484
Coordinator Dr IA O'Neil
Chemistry
Year CATS Level Semester CATS Value
Session 2008-09 M Level Second Semester 7.5

Aims

The aim of the module is to illustrate the formation and chemistry of the major families of natural products.


Learning Outcomes

By the end of the module, students should

  • understand the basic priciples of sugar chemistry, including the anomeric effect, protecting group strategies, selective functionalisation and sugar coupling methods,
  • recognise the role of organic cofactors in biosynthetic transformations,
  • understand the major biosynthetic pathway in theproduction of fatty acids, prostaglandins, polyketides, isoprenoids (including cholesterol), shikimic acids and aromatic amino acids, simple and complex alkaloids and b-lactams.

Syllabus
0 

Chemistry of sugars.

  • Introduction to sugars. Open and closed chain forms of glucose (mutarotation). Chemistry of open chain form of glucose. Formation of glycosides. The anomeric effect.
  • Selective protecting group strategies in glucose chemistry, including: Formation of anomeric halides, glycal formation and reactions, sugar ether derivatives, aldehyde and ketone derivatives.
  • Radical dexygenation reactions. The Hannessian reaction. Chemistry of sugar tosylates. Amino sugars.
  • Chemistry of polysaccharides. Sugar coupling reactions including anomeric halides and pseudohalides, trichloroimidates and sugar glycals. Synthesis of polysaccharides.

Introduction to metabolic pathways (catabolic and anabolic)

  • Elucidation of biosynthetic pathways using labelling techniques. The chemistry of organic cofactors and their role in biosynthetic pathways, including ATP, NAD, FAD, SAM, CoASH and Biotin. Glycolysis (glucose to acetyl CoA).

Fatty acid biosynthesis.

  • The chemistry of prostaglandins and related natural products. b-oxidation of fatty acids.

Polyketides.

  • Biosynthesis and chemistry of selected examples.

Isoprenoids.

  • Formation of isopentenylpyrophosphate. Chemistry of the major classes of terpenes. Formation of squalene and biosynthesis of lanosterol and cholesterol. Chemistry of sex hormones and vitamin D.

Shikimic acid formation.

  • Biosynthesis of aromatic amino acids. Mixed metabolites - Formation of flavanoids.
  • Biosynthesis of alkaloids, including role of pyridoxial phosphate in amio acid chemistry. Chemistry of pyrrolidine, piperidine, pyrrolizidine, ergot alkaloids, strychnine alkaloids.
Chemistry of b-lactams

Teaching and Learning Strategies

This material in this module is presented via a series of lectrues supported by two workshops.


Teaching Schedule
  Lectures Seminars Tutorials Lab Practicals Fieldwork Placement Other TOTAL
Study Hours 16

   6

       22
Timetable (if known) Tue 10-11am, Thurs Noon-1pm
  		           
Private Study 53
TOTAL HOURS 75

Assessment
EXAM Duration Timing
(Semester)		 % of
final
mark		 Resit/resubmission
opportunity		 Penalty for late
submission		 Notes
Written Examination  2 hours  second  100  August resit opportunity for PGT students only, where applicable. see notes    Year 3 (and Year 4) students resit at the next normal opportunity.  
CONTINUOUS Duration Timing
(Semester)		 % of
final
mark		 Resit/resubmission
opportunity		 Penalty for late
submission		 Notes
             

Recommended Texts
  • "Natural Products," J. Mann, R. S. Davidson, J. B. Hobbs, D. V. Banthorpe and J. S. Harborne, Longman, 1994.
  • "Chemical Aspects of Biosynthesis," J. Mann, Oxford Chemistry Primers, 1994.
  • "Medicinal Natural Products," P. M. Dewick, Wiley, 2002, 2nd Edition.
  • "An Introduction to Enzyme and CoenzymeChemistry," T. Bugg, Blackwell, 1997