CHEM 760/7600 - Carbohydrate Chemistry

Semester: Winter 2023

Professor: F.I. Auzanneau | Discipline: Organic | Campus: Guelph



  1. Structure of monosaccharides: configurations, ring size, conformations, mutarotation, anomeric effect
  2. Biological relevance of carbohydrates: disaccharides, oligosaccharides, polysaccharides, biosynthesis and synthetic biochemical tools
  3. Carbohydrate Synthetic Chemistry: A. Protecting groups in carbohydrate chemistry and synthetic strategies: Alkyls, acyls, silyls, acetals and ketals, selectivity etc… The daunting task of multi-step carbohydrate synthesis! B.The glycosylation reaction: when titans collide, the challenge of carbohydrate chemistry. Principle of glycosylation, armed-disarmed glycosyl donors, participating groups, anomeric effect and kinetic anomeric effect, glycosylation methods: Fisher, Koenigs-Knorr, Helfrich, thioglycosides, trichloroacetimidates and many others…
  4. NMR of carbohydrates: chemical shifts, coupling constants, 1D, 2D (real life examples)

Chemistry CHEM 760/7600 is a one-semester course in covering the chemistry and biological chemistry of carbohydrates. This course will apply concepts learned in Chem*2700 and Chem*3750 to carbohydrate molecules.

Specific Learning Objectives:

  1. To learn about the structural fundamentals of carbohydrates.
  2. To learn the basic biological importance of oligo-and polysaccharides.
  3. To learn fundamentals concepts of synthetic carbohydrate chemistry and to be able to design syntheses of organic molecules of moderate complexity.
  4. To learn then be able to use one dimension and two dimension NMR experiments to characterize synthetic molecules.
  5. To be able to survey the literature and identify a question that has yet to be answered in the area of glycobiology.
  6. To design a sound research proposal that would allow answering the question identified
  7. To learn the basic skills required to write a Grant proposal in the NSERC format.
  8. To concisely present the proposed research orally to a mixed audience.


There is no “official” text-book for this course. However the lecture content will be based on the following texts as well as literature examples:

    1. Title: Organic synthesis with carbohydrates
      Author: Boons, Geert-Jan. Hale, Karl.
      Publisher: Malden, MA: Blackwell Science, 2000.
    2. Title: Essentials of carbohydrate chemistry and biochemistry
      Author: Lindhorst, Thisbe K.
      Publisher: Weinheim : Wiley-VCH, c2003

Additional resources are:

Title: Preparative carbohydrate chemistry
Author: Hanessian, Stephen.
Publisher: New York : Marcel Dekker, c1997.

Title: Modern Methods in Carbohydrate Synthesis
Authors: Shaheer H. Khan, Roger A. O’Neill
Publisher: Harwood Academic publishers

Title: Carbohydrates in chemistry and biology
Authors: Ernst, Beat Hart, Gerald W, Sinaÿ, Pierre
Publisher: Weinheim ; New York : Wiley-VCH, c2000.

REQUIRED: TOPSPIN software– I will give you a set of data to print and analyze.

Other resources such as pdf files of literature articles as well as lecture material will be available for download from courselink throughout the semester.


Grades will be calculated as follow:

Presentation: 15%

Research Proposal and NMR practice: 15%

MidTerm: 35%

Final: 35%

NMR practice: This will be based on “real” set of NMR data.

Presentation and Research Proposal:

Each student will search the glycobiology literature and design an original research project. Such project could be aimed towards the synthesis of molecules relevant to glycobiology, method development for synthetic carbohydrate chemistry etc… You will write up this research proposal in an NSERC format, including Background/Relevance, descriptive short-term goals, long-term goals and impact. You will also be asked to provide an appropriate budget. We will have one meeting to discuss grant proposal writing.

Each student will present his/her proposal in class (10-15 min), outlining the topic of the study, and the method proposed (with details). The presentation will be followed by a 2 min discussion in class.

Midterm: The midterm examination will take place during class time on Monday March 6, Location: MACN 203



Depending on the number of students enrolled in the course we will have between about

9 lectures ONLINE

1 in-class midterm (March 6)

2 in class sessions (March 27, April 3) during which the students will give their presentations in person.


  • Mon: 7:00 pm - 9:20 pm in MacN 203

Office Hours

Dr. F.-I. Auzanneau University of Guelph Rm. 126 MacN Email: [email protected] Last minute information may be sent to you by email, make sure that you retrieve your mail regularly.