Module FXX-4501:
Structure & Reactivity (Org)

Module Facts

Run by School of Natural Sciences

10 Credits or 5 ECTS Credits

Semester 1

Organiser: Dr Patrick Murphy

Overall aims and purpose

To illustrate strategies to synthesise complex natural products and to apply concepts of retrosynthesis to strategic planning. Part of this is to advance students' knowledge of biological chemistry, highlighting the cross-disciplinary nature of this area. A particular emphasis will be on the understanding of the role of biological active compounds (e.g. enzymes and proteins, lectins, [complex] carbohydrates, and other biopolymers) in biological systems on molecular level, how to study and analyse such systems. Examples will be given to illustrate links to health and disease.

Course content

to illustrate strategic approaches to the total synthesis of selected natural products. One-third of the module introduces the students to a sub-discipline of natural products - glycobiology. It covers both chemistry and biology-related aspects.

Glycobiology – This section will introduce the role of carbohydrates in biological systems. Starting from basic concepts and terminology specific for carbohydrate chemistry, the following areas will be illuminated: properties and structures of common polysaccharides (e.g. amylose, cellulose, chitin, chitosan, peptidoglycans, pectins, dextrans, glycosaminoglycans, proteoglycans), chemical and enzymatic synthesis and degradation, complex carbohydrates (case studies: human and bacterial structures), glycoconjugates (case studies: glycoproteins, glycolipids), carbohydrates in medicine (case studies: lead structure, vaccine, inhibitor), carbohydrate recognition (case studies: lectins) in e.g. inflammatory processes (immune system), protein folding, blood group typing.

Course Team: (24 lectures)

RESOURCE IMPLICATIONS ESSENTIAL READING - None (literature mentioned in handouts) RECOMMENDED READING 1. Organic Chemistry, Jonathan Clayden, Nick Greeves, Stuart Warren and Peter Wothers (2nd Ed 2012) Classics in Total Synthesis: Targets, Strategies, Methods (Chemistry) 1st Edition by K. C. Nicolaou, E. J. Sorensen SPECIFIC RESOURCE IMPLICATIONS FOR STUDENTS - None

Assessment Criteria

threshold

a) Knowledge and understanding of course content is basic b) Problems of a routine nature are generally adequately solved; c) Transferable skills are at a basic level.

For students entering year 2 (level 5) after September 1st 2013 or MSc/MRes students, the threshold criteria are set as follows: Knowledge base covers all essential aspects of subject matter dealt with in the assignment; conceptual understanding is acceptable.
Problems of a familiar and unfamiliar nature are solved and solutions are acceptable. Performance in transferable skills is sound.

good

a) Knowledge and understanding of course content is good b) Problems of a familiar and unfamiliar nature are solved in a logical manner; solutions are generally correct and acceptable. c) Performance in transferable skills is sound and shows no significant deficiencies.

For students entering year 2 (level 5) after September 1st 2013 or MSc/MRes students, the threshold criteria are set as follows: Knowledge base covers all essential aspects of subject matter dealt with in the assignment and shows good evidence of enquiry beyond this. Conceptual understanding is good. Problems of a familiar and unfamiliar nature are solved in a logical manner; solutions are generally correct and acceptable. Performance

excellent

a) Knowledge and understanding of course content is outstanding. a) Problems of a familiar and unfamiliar nature are solved with efficiency and accuracy; problem-solving procedures are adjusted to the nature of the problem. b) Experimental work is exemplary and shows a through analysis and appraisal of experimental results, with appropriate suggestions for improvement. c) Performance in transferable skills is generally very good.

For students entering year 2 (level 5) after September 1st 2013 or MSc/MRes students, the threshold criteria are set as follows: Knowledge base is extensive and extends well beyond the work covered in the assignment; conceptual understanding is outstanding. Problems of a familiar and unfamiliar nature are solved with efficiency and accuracy; problem-solving procedures are adjusted to the nature of the problem. Performance in transferable skills is generally very good.

Learning outcomes

  1. Students should be able to select appropriate techniques and procedures to execute the synthesis of complex organic molecules.

  2. Students should be able to critically discuss the relationship of geometric and electronic structure of pi-conjugated systems, and to combine information from different physical methods to predict the properties of organic molecules and polymers. They should be able to explain physical-chemical principles of applications of pi-conjugated systems as materials for various organic electronic devices.

  3. On successful completion of the module, the student: should be able to discuss general principles of carbohydrate recognition and its role in biological systems (e.g. cell-cell communication).

  4. On successful completion of the module, the student: should demonstrate some fundamental knowledge about the role of carbohydrate recognition processes in health and disease.

  5. On successful completion of the module, the student: should be able to apply basic carbohydrate chemistry terminology.

  6. On successful completion of the module, the student: should be able to recognise and draw the chemical structure of common polysaccharides.

Assessment Methods

Type Name Description Weight
EXAM Examination 90
COURSEWORK Retrosynthesis workshop 10

Teaching and Learning Strategy

Hours
Lecture

This module includes 24 hours of lectures and tutorials, where active participation is required. It has been divided into three segments; one is on electronic structure and reactivity on conjugated PI-functional aromatic systems and another one is on for the synthesis of marine and terrestral natural products, the third one is an introduction to glycobiology. Private study 76 hours.

24
Private study 76

Transferable skills

  • Literacy - Proficiency in reading and writing through a variety of media
  • Numeracy - Proficiency in using numbers at appropriate levels of accuracy
  • Self-Management - Able to work unsupervised in an efficient, punctual and structured manner. To examine the outcomes of tasks and events, and judge levels of quality and importance
  • Information retrieval - Able to access different and multiple sources of information
  • Critical analysis & Problem Solving - Able to deconstruct and analyse problems or complex situations. To find solutions to problems through analyses and exploration of all possibilities using appropriate methods, rescources and creativity.

Subject specific skills

  • CC4 The ability to recognise and analyse problems and plan strategies for their solution
  • CC5 Skills in the generation, evaluation, interpretation and synthesis of chemical information and data
  • CC8 The ability to adapt and apply methodology to the solution of unfamiliar problems
  • PS2 Skills in the employment of common conventions and standards in scientific writing, data presentation, and referencing literature
  • PS3 Problem-solving skills, relating to qualitative and quantitative information
  • PS6 Information technology skills which support the location, management, processing, analysis and presentation of scientific information
  • PS16 The ability to work in multi-disciplinary and multi-skilled teams
  • SK1 Are fully conversant with major aspects of chemical terminology
  • SK2 Demonstrate a systematic understanding of fundamental physicochemical principles with the ability to apply that knowledge to the solution of theoretical and practical problems
  • SK3 Gain knowledge of a range of inorganic and organic materials
  • SK4 Demonstrate, with supporting evidence, their understanding of synthesis, including related isolation, purification and characterisation techniques
  • SK9 Read and engage with scientific literature
  • CC1 the ability to demonstrate knowledge and understanding of essential facts,concepts,principles and theories relating to theSubject areasCovered in theirProgramme
  • CC2 the ability to applysuch knowledge and understanding to thesolution of qualitative and quantitativeProblems that are mostly of a familiar nature
  • Consider issues from a range of interdisciplinary perspectives.

Courses including this module

Compulsory in courses:

Optional in courses: