The University of Western Ontario

Chemistry 4493
CHEMISTRY OF BIOLOGICAL MACROMOLECULES
Course Information - 2015
Instructor

Prof. Robert Hudson, Rm. ChB219A

rhhudson@uwo.ca

Website
Resources and other information will be available through OWL: https://owl.uwo.ca/portal
Description
A survey of the chemistry of carbohydrates, nucleosides and amino acids particularly in the context of the laboratory
synthesis oligosaccharides, polynucleotides and peptides.
Lectures

Chemistry Building, Room 115

Monday, Wednesday, Friday 9:30 am

Course Prerequisite

Chemistry 3373.

Required Messages from the Dean

1) Prerequisite
"Unless you have either the requisites for this course or written special permission from your Dean to enrol in it, you
will be removed from this course and it will be deleted from your record. This decision may not be appealed. You will
receive no adjustment to your fees in the event that you are dropped from a course for failing to have the necessary
prerequisites."
2) Plagiarism is a serious Scholastic Offence.
All work is to be done individually.
Plagiarism: Students must write their essays and assignments in their own words. Whenever students take an idea,
or a passage from another author, they must acknowledge their debt both by using quotation marks where
appropriate and by proper referencing such as footnotes or citations. Plagiarism is a major academic offence (see
Scholastic Offence Policy in the Western Academic Calendar).
All required papers may be subject to submission for textual similarity review to the commercial plagiarism
detection software under license to the University for the detection of plagiarism. All papers submitted for such
checking will be included as source documents in the reference database for the purpose of detecting plagiarism of
papers subsequently submitted to the system. Use of the service is subject to the licensing agreement, currently
between The University of Western Ontario and Turnitin.com (http://www.turnitin.com ).
Evaluation

Problem Sets*

Approximate dates: Oct. 5, Nov. 9, Dec. 4

In-Class Midterm Test, 2 x 50min.

Friday, October 9

20%

Friday, November 13

20%

Final Exam (3 hour): TBA

60%

*problem sets will serve as the basis for interactive tutorials. Attendance of the tutorial and participation in the discussion is highly recommended.

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Sources
There is no required textbook. Your previous organic chemistry textbooks will provide some of the introductory
material. Various other sources will be used throughout the course and a listing of those available through the
library is given below. Journal articles may be assigned for reading and discussion. Notes will be written on the
board, some supplements will be handed out when needed (e.g. overly complex drawings).
There are many relevant books that are available in the library, a sampling...
General:
Natural Products: Their Chemistry and Biological Significance, J. Mann, R.S. Davidson, J.B. Hobbs, D.V.
Banthorpe, J.B. Harborne. QD415.N365
Carbohydrates:
Carbohydrate Chemistry: Monosaccharides and Their Oligomers, H.S. El Khadem. QD321.E48 1988
Carbohydrate chemistry, edited by Geert-Jan Boons. QD321.C273 1998
Nucleic Acids:
Nucleic Acids in Chemistry and Biology, 2nd ed., G.M. Blackburn, M.J. Gait. QD433.N83 1996
or
Nucleic Acids in Chemistry and Biology: 3rd ed. G.M. Blackburn, M.J Gait, D. Loakes, D.M. Williams,
2006
Chemistry of Amino Acids, Peptides:
Peptides: Synthesis, Structures and Applications, B. Gutte. QU68.P4247 1995
The Practice of Peptide Synthesis, M. Bodanszky, A. Bodanszky. QD431.B763 1994

Solid phase peptide synthesis: a practical approach, E. Atherton, R.C. Sheppard QU68.A868s 1989

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Topics

Approximate Lectures

Introduction....................................................................................................................1
-overview
-biological macromolecules and their constituents
Protecting Group Chemistry, Polymer-Supported Chemistries, Automation................3
-concept of protecting groups and their use
-polymer supported chemistry
-machine-assisted synthesis
Carbohydrates..................................................................................................................8
monosaccharides
-structures and representations
-selected reactions of monosaccharides
oligosaccharides, polysaccharides
-chemical synthesis and applications of oligosaccharides
Nucleic Acids...............................................................................................................8
nucleosides
-chemical synthesis
-nucleoside-based antivirals, anticancer agents
nucleotides
-chemical synthesis
-phosphonate prodrugs
polynucleotides
-modern chemical synthesis
-nucleic acid analogues
-applications
Amino Acids, Peptides....................................................................................................8
amino acids
-structure, properties
-selected reactions
-chemical synthesis, historical and modern
oligopeptides
-peptide/protein structure
-chemical synthesis,
various protecting group strategies
modern reagents for amide bond formation
-applications for synthetic peptides and peptidomimetics

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Other Notes:
Accessibility
Please contact the course instructor if you require lecture or printed material in an alternate format or if any other
arrangements can make this course more accessible to you. You may also wish to contact Services for Students with
Disabilities (SSD) at 661-2111 ext. 82147 if you have questions regarding accommodation.
Support Services
Learning-skills counsellors at the Student Development Centre (http://www.sdc.uwo.ca) are ready to help you
improve your learning skills. They offer presentations on strategies for improving time management, multiple-choice
exam preparation/writing, textbook reading, and more. Individual support is offered throughout the Fall/Winter terms
in the drop-in Learning Help Centre, and year-round through individual counselling.
Students who are in emotional/mental distress should refer to Mental Health@Western
(http://www.health.uwo.ca/mental_health) for a complete list of options about how to obtain help.
Additional student-run support services are offered by the USC, http://westernusc.ca/services.
The website for Registrarial Services is http://www.registrar.uwo.ca.