CHEM20050 Medicinal Chemistry and Chemical Biology (level 2)

Academic Year 2024/2025

The module is comprised of four parts addressing biological molecules and principles of medicinal chemistry. Amino acids: structure, zwitterionic form, peptide synthesis (protection of NH2 and COOH, activation of COOH), conformational analysis of peptides, mass spectrometry of peptides and chymotrypsin mechanism. Carbohydrates: monosaccharides, structure analysis, conformation, alpha/beta anomers, glycosidic linkage (disaccharides, polysaccharides), glycosidase reaction. DNA: structure, targeting DNA in cancer therapy (cis-platin, doxorubicin), damages to DNA (base loss, deamination, chemical modification, photodamage), reactive oxygen species (radical reaction with nucleotides), antioxidant (vitamin A, E and C). Medicinal Chemistry: principles of rational drug design, identification of drug targets, structure-activity relationship (SAR), pharmacokinetics, ADMET principle.

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Curricular information is subject to change

Learning Outcomes:

At end of the module students should be able to:
Describe basic structure, properties and reactivity of amino acids and carbohydrates.
Apply the principles of conformational analysis of 'simple' organic molecules to understanding 'folding' in biological molecules. Describe the important reactions and reagents used in synthesis of biological molecules and describe the mechanism by which these reagents work and the usefulness of protecting group strategies. Describe selected chemical transformations of biomolecules. Apply selected physical techniques (NMR, MS) to obtaining information on the structure of biological molecules.
Apply and relate the principles of organic reaction mechanism to processes in biology and relate this to development of small molecules that can be useful as tools for studying biological systems or as drugs. Describe the basics of molecular recognition. Understand the principles of medicinal chemistry.
Perform a series of laboratory techniques and experiments required for synthesis, biotransformations, purification, isolation and (kinetic) analysis of biological molecules.
Carry out these laboratory procedures safely.

Indicative Module Content:

Basic structure, properties and reactivity of amino acids, nucleic acids and carbohydrates.
Principles of conformational analysis of 'simple' organic molecules and application to 'folding' of proteins.
Introduction to protecting group chemistry for carbohydrates and amino acids.
Basic reactions and reaction mechanisms for amino acids, nucleic acids and carbohydrates.
Selected chemical transformations of biomolecules (basics of DNA, RNA and protein synthesis).
Use of enzymes as catalysts for organic synthesis.
Use of physical techniques (NMR, MS) to obtaining information on the structure of biological molecules.
Application of principles of organic reaction mechanisms to processes in biology and the development of small molecules that can be useful as tools for studying biological systems or as drugs (e.g., AZT, anti-cancer drugs, anti-oxidants).
The basics of molecular recognition. The principles of medicinal chemistry.
Laboratory techniques: TLC, reduced pressure distillation, rotary evaporation, liquid-liquid separations with sep. funnels, natural product extraction, recording UV spectra and monitoring an enzymatic reaction by UV spectroscopy, protecting group reactions, dipeptide synthesis.

Student Effort Hours: 
Student Effort Type Hours
Lectures

24

Tutorial

4

Practical

24

Specified Learning Activities

8

Autonomous Student Learning

48

Total

108

Approaches to Teaching and Learning:
Lectures; laboratory-based learning; active/task-based learning; case-based learning; tutorials and problem-based learning. 
Requirements, Exclusions and Recommendations
Learning Requirements:

This module requires an understanding of basic organic chemistry. CHEM10050 is required.

Learning Recommendations:

CHEM20040


Module Requisites and Incompatibles
Pre-requisite:
CHEM10050 - Basis of Organic & Biol Chem


 
Assessment Strategy  
Description Timing Open Book Exam Component Scale Must Pass Component % of Final Grade

Not yet recorded.


Carry forward of passed components
Yes
 
Resit In Terminal Exam
Autumn Yes - 2 Hour
Please see Student Jargon Buster for more information about remediation types and timing. 
Feedback Strategy/Strategies

• Feedback individually to students, post-assessment
• Group/class feedback, post-assessment

How will my Feedback be Delivered?

Feedback will be given on Lab reports by return of the report with annotations and laboratory demonstrators will give oral feedback to groups and/or individuals. Feedback will be given on homework assignments by tutors by return of the assignments with written annotations and tutors will give oral feedback to groups during tutorials.

Recommended Reading: Books with title “Organic Chemistry” will tend to have chapters dedicated to amino acids, proteins, carbohydrates and nucleic acids, e.g., McMurry (547.MCM)
An Introduction to Medicinal Chemistry, G.L. Patrick; Oxford University Press; 615.19 PAT. Use the index to find parts directly about the drugs described in the course. There is also material of broader interest.
Concepts of Genetics, W.S. Klug, M.R. Cummings; 576.5 KLU [Part two – The molecular basis of heredity, tackles many topics related to the course.]

Other Suggestions:
Foundations of Chemical Biology, C.M. Dobson, J.A. Gerrard, A.J. Pratt; Oxford Chemistry Primer; 572.DOB; This has some sections related to the course.
Free Radicals in Biology and Medicine, B Halliwell and J. M.C. Gutteridge, Oxford Science Publications, 3rd Ed. 572.33Hal: Chapter 3.22 Ascorbic acid, Vitamin E; Chapter 3.23 Carotenoids; Chapter 4.6/4.7/4.8 – Oxidative stress, damage to DNA. This book is slightly more advanced but there are a sub-sections related to the course if you are especially interested.
Name Role
Assoc Professor Eoghan McGarrigle Lecturer / Co-Lecturer
Professor Stefan Oscarson Lecturer / Co-Lecturer
Miss Vanessa Becker Tutor
Bodhayan Biswas Tutor
Mr Ruairi Crawford Tutor
Camilla Di Girolamo Tutor
Mr Kacper Kluza Tutor
Ms Aoife Martin Tutor
Mr Fionn McNeill Tutor
Ms Dairine Morgan Tutor
Mr Paul Nolan Tutor
Kathryn Yeow Tutor