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.

The University of Western Ontario 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

The University of Western Ontario

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

The University of Western Ontario

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.