Fall 2019 - CHEM 452 D100

Bio-organic Chemistry (3)

Class Number: 10691

Delivery Method: In Person

Overview

  • Course Times + Location:

    Tu, Th 2:30 PM – 4:20 PM
    AQ 5006, Burnaby

  • Exam Times + Location:

    Dec 11, 2019
    3:30 PM – 6:30 PM
    AQ 5019, Burnaby

  • Prerequisites:

    CHEM 380 and MBB 222, both with a minimum grade of C-, or permission of the Department.

Description

CALENDAR DESCRIPTION:

An advanced treatment of the use of enzymes in organic synthesis, the use of stable and radioisotopes in the study of enzymatic processes and the design of enzyme inhibitors. Quantitative.

COURSE DETAILS:

This course will provide an overview of natural products and their biosynthetic origin. The course will begin with the synthetic building blocks and strategies used in living systems. Next, we shall cover primary metabolic pathways and later move on to complex secondary metabolites. Behind the bewildering complexity and variety of natural product biosyntheses there are a few elegant recurring patterns, which we shall highlight.

Topics:

1. Biochemical "reagents":  nucleotide triphosphates, nicotinamide cofactors, flavins, coenzyme A, lipoic acid, pyridoxamine/pyridoxal, thiamine phosphate, biotin, folate, vitamin B12, S-adenosyl methionine

2. Primary metabolism: carbohydrates

2.1 glycolysis
2.2 TCA cycle
2.3 pentoses, tetroses
2.4 carbon fixation from CO2

3. Nucleic acids
3.1 DNA/RNA structure and replication (brief overview)
3.2 nucleotide biosyntheses pyrimidines, purines, 2'deoxyribonucleotides

4. Proteins and peptides
4.1 ribosomal
4.1.1 amino acid activation; transfer RNA
4.1.2 translation
4.1.3 post-translational modifications (brief overview)
4.2 non-ribosomal cases: siderophores, §-lactam antibiotics, nitrile-containing products, glucosinolates

5. Fatty acids
5.1 biosynthesis (elongation, desaturation)
5.2 fatty acid derivatives
5.2.1 alkanes and aliphatic pheromones
5.2.2 prostaglandins
5.2.3 thromboxanes
5.2.4 leukotrienes

6. Polyketides and phenolics
6.1 polyketide synthases: comparison to fatty acid synthases
6.2 cases: erythromycin (open-chain procursor, release, postPKS enzymes), avermectin, brevetoxin A (polyethers), lovastatin, phenolics
6.3 overview of polyketides diversity

7. Terpenes
7.1 general introduction, classification
7.2 electrophilic condensation reaction
7.3 precursor formation: mevalonate pathway
7.4 precursor formation: 1-deoxyxylulose-5-phosphate pathway
7.5 modifications
7.5.1 head-to-head condensation
7.5.2 cyclization
7.5.3 functionalization

8. The Shikimate pathway: another route to phenolics

9. Alkaloids
9.1 biologically accessible sources of N
9.2 amino acid biosynthesis
9.2.1 glutamate family
9.2.2 serine family
9.2.3 aspartate family
9.2.4 pyruvate family
9.2.5 aromatic family
9.2.6 histidine
9.3 alkaloid biosynthesis
9.3.1 derived from amino acids (ornithine, lysine, tyrosine, tryptophan, anthranilic acid and histidine)
9.3.2 derived from nicotinic acid
9.3.3 derived from acetate
9.3.4 derived from purine

Grading

  • Midterm Exam (Open Book) 20%
  • Term Paper 40%
  • Final Exam (Open Book) 40%

Materials

MATERIALS + SUPPLIES:

None

REQUIRED READING:

Dewick. Medicinal Natural Products: A Biosynthetic Approach. 3rd Ed. 2009. Publisher: Wiley.

RECOMMENDED READING:

Mann, Harborne and Davidson. Natural Products: Their Chemistry and Biological Significance. 1994. Publisher: Longman Publishing Group.

Michal & Schomburg. Biochemical Pathways: An Atlas of Biochemistry and Molecular Biology. Publisher: Wiley.

Department Undergraduate Notes:

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

Registrar Notes:

SFU’s Academic Integrity web site http://www.sfu.ca/students/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

ACADEMIC INTEGRITY: YOUR WORK, YOUR SUCCESS