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.

Contact hours:

Ìý	Autumn	Spring	Summer
Lectures		14
Tutorials		2
Supervised time in studio/workshop		10
Guided independent study:		74
Ìý	Ìý	Ìý	Ìý
Total hours by term	0		0
Ìý	Ìý	Ìý	Ìý
Total hours for module	100

Summative Assessment Methods:

Method	Percentage
Written exam	50
Written assignment including essay	30
Oral assessment and presentation	20

Summative assessment- Examinations:

1.5 hour.Ìý

Summative assessment- Coursework and in-class tests:

Synthesis exercise: 50%. Students will attend seminars to assist with a team chemical synthesis problem. Each student will be assessed by an individual written piece of work (30%) and by giving a team oral presentation on their work (20%) andÌýin each case we will examine how the team worked together to achieve the common goal as well as the individual’s work. Submission dates as detailed on Blackboard.

Formative assessment methods:

Feedback in seminars to assist with a team chemical synthesis problem.

Students will attend tutorials on the lecture material covered in this module. Attendance is compulsory. Tutorials to be submitted as detailed on Blackboard.

Penalties for late submission:

The Support Centres will apply the following penalties for work submitted late:

• where the piece of work is submitted after the original deadline (or any formally agreed extension to the deadline): 10% of the total marks available for that piece of work will be deducted from the mark for each working day (or part thereof) following the deadline up to a total of five working days;
• where the piece of work is submitted more than five working days after the original deadline (or any formally agreed extension to the deadline): a mark of zero will be recorded.

The University policy statement on penalties for late submission can be found at:
You are strongly advised to ensure that coursework is submitted by the relevant deadline. You should note that it is advisable to submit work in an unfinished state rather than to fail to submit any work.

Assessment requirements for a pass:
An overall mark of 50%.

Reassessment arrangements:

Reassessment arrangements are in accordanceÌýwith University policy. Reassessment of the written examination (50%) is heldÌýduring the University administered re-examination period in August.ÌýFailed coursework (a written report worth 30% and an oral presentation worth 20%) may be re-assessed by an alternative assignment beforeÌýor during the August re-examination period.



Final year students are not eligible to resit this module unless they have failed their degree programme overall.

Additional Costs (specified where applicable):

1) Required text books:Ìý None

2) Specialist equipment or materials:Ìý None

3) Specialist clothing, footwear or headgear:Ìý None

4) Printing and binding:Ìý None

5) Computers and devices with a particular specification:Ìý None

6) Travel, accommodation and subsistence:Ìý None

Last updated: 1 July 2021