Fall 2018 - CHEM 459 E100

Special Topics in Organic Chemistry (3)

Modern Glycoscience

Class Number: 5355

Delivery Method: In Person


  • Course Times + Location:

    Mo, We 4:30 PM – 6:20 PM
    AQ 5005, Burnaby

  • Exam Times + Location:

    Dec 12, 2018
    7:00 PM – 10:00 PM
    AQ 5005, Burnaby

  • Prerequisites:

    CHEM 380 or permission of the instructor.



An advanced, in-depth treatment of a specialized area of organic chemistry.


Combined graduate course: CHEM 759 - Special Topics in Organic Chemistry (3)

The aims of the course are to provide an introduction and overview of three branches of glycoscience; carbohydrate chemistry, carbohydrate biochemistry, and glycobiology. Literature papers will be used as case studies and recent papers will be presented as seminars by the class.  

NOTE: Chemistry, Biochemistry, and Biology majors are all welcome to take this class. Students write all sections of the midterm but choose which 2 of the 3 areas of the exam they receive their grade on selecting from (1) Carbohydrate Chemistry, (2) Carbohydrate Biochemistry, (3) Glycobiology. In this way students from different disciplines are exposed to other areas but are not graded beyond a basic pass/fail comprehension in the area with which they are least familiar.  

Introduction: (2-3 total of 1 hour lectures)

  • Formulae, projection systems, nomenclature, mutarotation, pseudorotational itineraries.  
Carbohydrate Chemistry: (6-8 total of 1 hour lectures)
  • Protecting groups:                        
    • Anomeric centre (Thiols, ethers, esters)                        
    • Hydroxyl (Esters, ethers, silyl ether)                        
    • Diols (Cis, trans, orthoesters)                        
    • Site selective groups (Benzylidene, trityl)                        
    • Amino (Masked, protecting groups)                        
    • Carboxyl                     
  • Glycoside Synthesis:                        
    • Latent versus armed                        
    • Donors (thioglycosides, TCA, halides)                        
    • General strategies
    • Block / stepwise / one pot                        
  • Ring functionalization:                        
    • Halogenation                        
    • Deoxygenation                        
    • Nitrogen installation               
  • Examples:                        
    • Inhibitor synthesis                        
    • Oligosaccharide synthesis  
Carbohydrate Biochemistry: (5-7 total of 1 hour lectures)
  • Biosynthetic pathways (NDP-sugars)            
  • Carbohydrate binding modules (CBMs)            
  • Enzyme mechanism
    • Hydrolases, transferases, aldolases, epimerases            
  • Inhibitors                        
    • Hydrolases, transferases, epimerases            
  • Chemoenzymatic syntheses
    • Recycling, factory, glycosynthase, transglycosylation            
  • Examples:                        
    • Inhibitors of transferases and glycosidases                                    
Glycobiology: (7-9 total of 1 hour lectures)
  • Structure of the cell (secretory pathway, glycocalyx)                                    
  • Localization of enzymes
  • Types of sugars in eukaryotes (review)
  • Glycans            
    • O-GalNAc cores            
    • N-Glycan core
    • O-Mannosylation
    • O-Fucosylation
    • O-Glucosylation
    • Proteoglycans
  • Glycosphingolipids            
    • Biosynthesis            
    • Localization and receptor control
  • Lectins, galectins, siglecs in biology            
    • P-selectin in inflammation            
    • Role in the immune system
  • Examples:            
    • Protein quality control            
    • Blood group antigens      
    • Cell surface residency - galectin lattice


  • Midterm Exam 30%
  • Literature Presentations 30%
  • Questions for Presenters 20%
  • Research Proposal 20%


  • Midterm (2 hours) – write all sections [NOTE: students write all three sections of the midterm but choose which 2 of the 3 areas of the exam they receive their grade on selecting from (1) Carbohydrate Chemistry, (2) Carbohydrate Biochemistry, (3) Glycobiology. Students receive a pass/fail for the topic not selected and are graded on the other 2 sections.]   
  • Literature presentations – Summarize one topic from list.
  • Questioners (for literature presentations).
  • Research proposal (expansion work on literature).

Department Undergraduate Notes:

A grade of C- or better is required for all prerequisite courses.

Registrar Notes:

SFU’s Academic Integrity web site http://students.sfu.ca/academicintegrity.html is filled with information on what is meant by academic dishonesty, where you can find resources to help with your studies and the consequences of cheating.  Check out the site for more information and videos that help explain the issues in plain English.

Each student is responsible for his or her conduct as it affects the University community.  Academic dishonesty, in whatever form, is ultimately destructive of the values of the University. Furthermore, it is unfair and discouraging to the majority of students who pursue their studies honestly. Scholarly integrity is required of all members of the University. http://www.sfu.ca/policies/gazette/student/s10-01.html