CH4O4-Oligosaccharides and Natural Products

Module Provider: Chemistry
Number of credits: 10 [5 ECTS credits]
Level:7
Terms in which taught: Spring term module
Pre-requisites:
Non-modular pre-requisites:
Co-requisites:
Modules excluded:
Current from: 2021/2

Module Convenor: Dr Philippa Cranwell
Email: p.b.cranwell@reading.ac.uk

Module Co-convenor: Dr James Cooper
Email: james.cooper@reading.ac.uk

Type of module:

Summary module description:

You’ve learnt the basics of organic chemistry during the first three years of your degree. Now you are ready for some more in-depth studies of exciting topics at the frontiers of this multi-disciplinary science! Learn how to approach the synthesis of a complex organic molecule through a programmed series of workshops given by experienced medicinal chemists. Discover the world of oligosaccharides and study their chemical synthesis from lectures by an expert in the field. Marvel at the diversity of natural products that have inspired organic chemists for centuries, but have only recently revealed their biosynthetic secrets. This is an essential course for anyone planning a future career that will involve organic chemistry!

Aims:
To enable the student to gain an understanding of the breadth of modern chemistry and demonstrate that organic chemistry is a multi-disciplinary science. Additionally, students will take part in a group-based problem solving exercise that will help them to understand how a medicinal chemist applies synthetic organic chemistry to the development of a drug.

Assessable learning outcomes:

Students who have successfully completed this module will be able to:

• Understand the biological role played by complex carbohydrates and describe current synthetic methodology for the construction of such molecules.


• Outline the different classes of secondary metabolites and describe their biosynthesis.


• Carry out an analysis of the synthesis of a potential drug and design routes to prepare analogue structures.


• Dem onstrate an ability to plan a synthesis to deliver a range of compounds for a drug discovery programme.

Additional outcomes:

Outline content:

Synthesis in Medicinal Chemistry (10 workshops) – In this part of the course the class will be split into teams and each team assigned a synthetic, medicinal chemistry task. The team will be charged with completing the task set through appropriate division of labour. The problem will rely heavily on synthetic chemistry and the students’ ability to research the literature, taking advantage of databases such as Reaxys and SciFinder. The exercise will be assessed via an oral and writ ten component. Feedback and guidance is available during the timetabled workshops.

Oligosaccharides (6 hours). Different strategies for the synthesis of oligosacharrides of biological significance will be discussed, including enzymatic and solid phase syntheses.

Natural Products and their Biosynthesis (8 hours). Most classes of secondary metabolites will be covered, including terpenoids and steroids (derived from both the mevalonate and DXP pathways), alka loids (derived from amino acids) and acetogenins. In addition to their biosynthesis, the medicinal and/or toxicological importance of natural products will be stressed, as well as their ecological significance.

Brief description of teaching and learning methods:
10 x 1 hour workshop seminars. 14 x 1 hour lectures with 2 associated tutorials.
Summer hours are scheduled for revision.