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CH271 - Mechanistic and Biological Chemistry

  • Module code: CH271
  • Module name: Mechanistic and Biological Chemistry
  • Department: Chemistry
  • Credit: 15

Content and teaching | Assessment | Availability

Module content and teaching

Principal aims

Conformation and stereochemistry are crucial in understanding how molecules interact. Initially, compounds containing a stereogenic carbon, (or another element) will be reviewed as an introduction to axial and helical chirality. A discussion of the effect of strain on the conformational preferences in acyclic molecules will lead onto the boat and chair forms of cyclohexane. Elimination reactions in these ring systems will be used to illustrate the requirement of orbital overlap in syn/anti elimination mechanisms. Guidance on elucidating reaction mechanisms using rate data, substituent effects and isotopic labeling will be illustrated with examples of hydrolysis, additions, eliminations and ring closure reactions. Factors that favour the chair conformation of cyclohexanes will inform the conformational preferences of monosaccharides but an additional stereoelectronic factor (the alpha effect) that influences conformational preference in the glycoside bond will also be introduced. The principles of general acid/base and specific acid/base catalysis will be explained and the importance of these factors in hydrolysis and enzyme catalysis. The second half of the module will be an introduction to biological and medicinal chemistry. The principles of carbohydrate chemistry will be discussed, including stereoelectronic effects and synthetic methods. A more detailed discussion of enzyme catalysis will cover transition state theory and Michaelis-Menten kinetics and the use of enzymes for biocatalysis and enantiomer resolution. An introduction to medicinal chemistry will cover enzyme inhibitors, the role of receptors, and examples of receptor agonists and antagonists for adrenaline, acetylcholine and histamine receptors.

Principal learning outcomes

By the end of the module the student should be able to Assign C-I-P (R/S) nomenclature to a range of stereogenic centres including non-carbon centres. Be able to competently draw a range of three-dimensional molecules in two dimensions and appreciate key stereochemical conventions. Appreciate that stereochemistry is not necessarily associated with a stereogenic centre. Give examples of helically and axially chiral molecules. Be able to carry out conformational analysis of simple acyclic and cyclic molecules using appropriate diagrams (Newman projections, chair / boat structures). Explain the effect of ring size on energy and conformation of small and medium sized rings. Explain in mechanistic terms how conformation in cyclic systems directly affects reactions such as base catalysed (E2) eliminations in cyclic systems. Appreciate importance of enantio- and diastereotopism. Understanding of the mechanistic concept to describe chemical reactions and awareness of some of the tools to derive mechanistic insight Construction of a reaction profile based on kinetic and thermochemical properties of a chemical reaction. Confident design of labelling experiments to obtain mechanistic insight into the reaction. Understanding of the concept of kinetic isotope effects and its use to determine energetic and geometrical changes. Understand and explain the structures, reactivity and synthesis of monosaccharides, disaccharides, and polysaccharides; answer problem-based questions on these topics Understand and explain the molecular basis for enzyme catalysis, enzyme structure, and Michaelis-Menten enzyme kinetics; answer problem-based questions on these topics Understand the principles and practices of introductory medicinal chemistry, examples of drug action through enzyme inhibition and receptor binding; assess structure-activity data and answer problem-based questions on these topics

Timetabled teaching activities

30 hrs lectures (3 hrs a week) 2 hrs workshops 4 hrs tutorials 2 hrs revision workshops

Departmental link

go.warwick.ac.uk/CH271

Module assessment

Assessment group Assessment name Percentage
15 CATS (Module code: CH271-15)
D (Assessed/examined work) Workshop reports 20%
  1.5 hour examination (Summer) 80%

Module availability

This module is available on the following courses:

Core
  • Undergraduate Chemistry 3 Year Variants (F100) - Year 2
  • Undergraduate Chemistry (with Intercalated Year) Variants (F101) - Year 2
  • Undergraduate Master of Chemistry Variants (F105) - Year 2
  • Undergraduate Master of Chemistry (with Intercalated Year) (F107) - Year 2
  • Undergraduate Master of Chemistry (with International Placement) (F109) - Year 2
  • Undergraduate Master of Chemistry Variants (F109) - Year 2
  • Undergraduate Master of Chemistry (with Industrial Placement) (F110) - Year 2
  • Undergraduate Master of Chemistry Variants (F110) - Year 2
  • Undergraduate Master of Chemistry (with International Placement) (F111) - Year 2
  • Undergraduate Master of Chemistry (with Industrial Placement) (F112) - Year 2
  • Undergraduate Chemistry 3 Year Variants (F121) - Year 2
  • Undergraduate Chemistry (with Intercalated Year) Variants (F122) - Year 2
  • Undergraduate Master of Chemistry Variants (F125) - Year 2
  • Undergraduate Master of Chemistry with Medicinal Chemistry(with Intercalated Year) (F127) - Year 2
  • Undergraduate Chemistry and Business Studies (FN11) - Year 2
Optional Core

N/A

Optional

N/A