Download Part B: Biological Organic Chemistry

School of Biomedical Biomolecular and Chemical Sciences
Unit Outline
Biological & Medicinal Chemistry
CHEM2221
Semester: 2
Campus: Crawley
Unit Coordinator: Professor Sue Berners-Price
This outline is the currently available version for this unit. Detailed Information on unit
content and assessment may undergo modification before the time of delivery of the
unit. For the most up to date information students must consult material supplied to
enrolled students by the unit co-ordinator.
All material reproduced herein has been copied in accordance with and pursuant to a statutory licence administered
by Copyright Agency Limited (CAL), granted to the University of Western Australia pursuant to Part VB of the
Copyright Act 1968 (Cth).
Copying of this material by students, except for fair dealing purposes under the Copyright Act, is prohibited. For the
purposes of this fair dealing exception, students should be aware that the rule allowing copying, for fair dealing
purposes, of 10% of the work, or one chapter/article, applies to the original work from which the excerpt in this course
material was taken, and not to the course material itself
© The University of Western Australia 2001
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Introduction
This unit covers both inorganic and organic chemistry relevant to biological systems. Topics
include the chemistry of biomolecules, carbohydrates, proteins, lipids and oligonucleotides,
addressing their stereochemistry, structure, synthesis, biosynthesis and importance in living
systems. The bioinorganic component provides an introduction to the role of metal ions in
biology, with an emphasis on the fundamental transition metal chemistry relevant to the
mechanisms of metalloenzymes and metal-based drugs.
Broad Learning Outcomes
Outcomes
Assessment Activity
Students will be able to recall and integrate key knowledge
and concepts about:
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Inorganic chemistry relevant to biological systems
Basic facts, principles and theories of organic chemistry.
Problems at the biology/chemistry interface
Chemical terminology, nomenclature and conventions
associated with each group of compounds
Functional groups, their reactivity and interconversion.
Structure, reactivity and role of key biomolecules.
Lab Reports
Theory exam
Students will acquire skills in:
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Performing standard laboratory procedures for simple
synthetic organic inorganic and analytical chemistry
Use of instrumentation and interpretation of
spectroscopic data for structure determination of
inorganic and organic compounds
Retrieving information from a variety of sources,
including libraries, databases and the www
Lab Reports
Problem Sheets/Final Exam
Students will clearly communicate in writing the results of
laboratory work and reading using correct scientific style
Lab reports
Students will present scientific material and arguments
clearly, logically and correctly, in writing
Lab Reports/Final Exam
Advisable Prior Study
12 pts of 1st year Chem - CHEM2210 Structure Determination and Physical Chemistry
(Prerequisite).
Technical Requirements
Safety in Laboratory
Lab Coats and Safety Glasses must be worn in the laboratory at all times. General
instructions on laboratory safety are provided in the laboratory notes.
Laboratory Notebook
You must record everything during laboratory classes in a dedicated Notebook. The notebook
must have a hard cover, with pages that are properly bound (a Science Exercise Book with
graph paper/ruled pages interleaved is very suitable).
Calculator
You should have a pocket calculator available for use in the laboratory.
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Software Requirements
None
Contact Details
Unit web site (may include Web CT URL): http://Webct.uwa.edu.au/
Name of Unit coordinator: Prof. Sue Berners-Price
e-mail: [email protected]
Phone: 6488 3258
Fax: 6488 1005
Consultation hours: By appointment
Unit Structure Summary
Lectures
Three 1-hour lectures per week.
Practical and/or Laboratory Sessions
Two 3 hr laboratory classes per week for six weeks. Attendance is compulsory.
Topics
For details of times and venues of all teaching sessions please consult the most recent
version of the university timetable at http://www.timetable.uwa.edu.au/
LECTURE TOPICS
Part A: Biological Inorganic Chemistry
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Introduction. The essential elements. Functions of inorganic elements in biological
systems. Examples of metal binding sites in biological systems.
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Coordination Chemistry. Transition metal complexes. Types of ligands.
Stereochemistry
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Bonding in transition metal complexes: Crystal field theory, Ligand field theory. Ligand
field stabilisation energy and Pairing energy
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Spectral and magnetic properties of transition metal complexes. Magnetic moment.
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-bonding. The spectrochemical series.
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Consideration of the thermodynamic stability of metal bindings sites: formation
constants; Irving-Williams series, theory of Hard and Soft Acids and Bases; chelate
effect. Chelation therapy
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Kinetics of ligand substitution reactions important in biology: roles of Na + and K+; Ca2+
as a trigger of rapid events; biological activity of metal-based drugs.
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Specific examples of metalloenzymes. Carbonic anhydrase – a Zn metalloenzyme.
Electron transfer proteins in photosynthesis – plastocyanin, cytochromes and iron-sulfur
proteins. Metalloproteins involved in the transport and activation of O 2: haemoglobin,
myoglobin and cytochrome P450.
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LECTURE TOPICS continued
Part B: Biological Organic Chemistry
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Carbohydrates: Photosynthesis. Monosaccharides; aldoses and ketoses (uloses).
Stereochemistry; configuration, Fischer projection formulae, D/L sugars. Aldotetroses,
aldopentoses and aldohexoses. Cyclic forms; pyranose, furanose, conformation,
anomers, mutarotation. Typical reactions of monosaccharides. Glycosides; synthesis
and biosynthesis. Metabolism of glucose. Disaccharides; lactose, sucrose, cellobiose,
maltose. Polysaccharides, cellulose, starch, glycogen, chitin, blood-group substances.
Methods of determination of structure. Cyclodextrins. Carbohydrates as chiral starting
materials for the synthesis of other bioactive compounds. Vitamin C, ribose and
deoxyribose.
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Amino acids and proteins: Amino acids, structure, classification and properties.
Chemical synthesis, resolution, separation, enzymatic synthesis, biosynthesis. Peptides,
peptide bonds, Primary structure (Edman and enzymatic methods). Strategies in peptide
synthesis. Secondary structure.
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Nucleic Acids: Heterocyclic aromatic compounds. Purine and pyrimidine bases,
nucleosides, nucleotides, ATP, RNA, DNA (1o and 2o structure). Factors that affect
hydrogen bonding. Approaches to the synthesis of nucleosides and nucleotides.
Antiviral nucleosides.
References, Resources and Reading Materials
Recommended Text
Part A: Biological Inorganic Chemistry
“Inorganic Chemistry”, Shriver, and Atkins, 3rd edition. Chapters 7, 13 and 19
“Biocoordination Chemistry”, D.E. Fenton, Oxford University Press (1995).
Further Reading
“Principles of Bioinorganic Chemistry”, S.J. Lippard and J.M. Berg, Univ. Science Books
1994
Part B: Biological Organic Chemistry
"Organic Chemistry" J. McMurry, 6th Edition (2004) (Previous editions of this textbook can also
be used)
Further Reading
“Organic Chemistry”, J. Clayden, N. Greeves, S. Warren and P. Wothers. Oxford University Press
2001
Unit Web Site
All enrolled students have access to the unit WebCT site (http://webct.uwa.edu.au). This site
will be used for notices, posting of handouts and lecture notes for Part A (Biological Inorganic
Chemistry)
Assessment Details
Assessed Work
% Mark
Timing
Laboratory reports
20%
Usually due within 1-2 weeks of
completing each set of experiments
Final exam- 3hr exam.
80%
End of semester exam period
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Plagiarism
The University of Western Australia takes very seriously the matter of academic misconduct
by students and has policies in place that define misconduct (including plagiarism) and the
penalties that apply. The consequences for misconduct can be severe, including exclusion
from the university.
All students are expected to make themselves aware of the definitions and policies relating to
academic misconduct, found at the websites below, and with any additional requirements or
stipulations that may be provided by individual unit co-ordinators.
http://www.secretariat.uwa.edu.au/__data/page/20839/StuMiscondInfo.rtf
http://www.teachingandlearning.uwa.edu.au/tl/academic_conduct
When you obtain authority to log in to the unit website, you will see an online module on
academic conduct which you are strongly advised to complete in your own time.
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