Natural Products. Chemistry 624. Fall 2000.
Mondays, 6-9 PM, Beury Hall, Room 404
Instructor: D. Dalton, Beury Hall Room 340;
Office Hours: MWF 9:30-10:30; 11:30-12:30 and other times by appoiontment;
Telephone 215-204-7138
Facsimile 215-204-1532
e-mail dalton@astro.ocis.temple.edu;
or web site http://astro.temple.edu/~dalton
The previous text for this course was Natural
Product Chemistry, by Kurt B. G. Torssell. The subtitle of the text is "A mechanistic,
biosynthetic and ecological approach". The text was published by
APOTEKARSOCIETETEN (the Swedish Pharmacetuical Society). Apparently it is no longer in
print but should you have a copy, its use is acceptable. Thus, the text (which is available) and
is in the T.U. Bookstore has been changed to
Medicinal Natural Products by Paul M. Dewick. The latter is a John Wiley & Sons text and may also probably be purchased elsewhere.
While it is NOT necessary to own a Biochemistry text for this course, it would be a
good idea to be able to consult one from time-to-time.
As a consequence...
Revised Tentative Syllabus
Chemistry 624 (Natural Products), Fall 2000
Weeks 1 - 4
- Light and dark reactions (light harvesting porphyrin, Calvin cycle, Krebs cycle)
- Carbohydrates (brief introduction using ribulose-1,5-diphosphate in the Calvin cycle)
- Acetate from pyruvate (phosphoenolpyruvate - PEP)
- Shikimic acid, prephenic acid
- Polyketide synthases (PKS)
- Fatty acid biosynthesis
- Prostaglandins (PGF), Erythronolides (erythomycin), polycyclic aromatics
(usnic acid, etc., daunomycinone)
Weeks 5 - 8
- Acetate to mevalonate, isopentenyl pyrophosphate, dimethylallyl pyrophosphate
- Terpenes, sesquiterpenes (longifolene) polycyclic Isoprenoids (gibberellic acid,
progesterone)
Weeks 9 - 13 Alkaloids
End with porphyrins,(B12).
In the last two weeks, students will be expected to present a BRIEF talk on some aspect
of the material covered.
Chapter 1 is
devoted to an "overview" and some general concepts about what constitutes the study of "Natural Products". Chapter 2 is about
"secondary" metabolism. There is no longer a chapter on
"Chemical Ecology" and the treatment of chemical defense (plant and animal),
pheromones, plant-plant relationships, etc.. Much of which is speculation and
anthropomorphic rationalization. Thus, comments in this text, interwoven into the fabric of other
discussions should be treated accordingly.
It is not my intention to cover the material in Chapter 1. You will be expected to read
it and understand what is there. I will deal with questions you have as best I can.
Throughout the course will be an effort will be made to
BRIEFLY touch on major pathways biochemical pathways (although these are being
revised at a rapid pace and representative
examples of the chemistry of:
- Carbohydrates and primary metabolites,e.g.
- The shikimic acid pathway (including coumarins, quinones and lignin constituents)
- The polyketide pathway
- The mevalonic acid pathway. Terpenes
- Amino acids, peptides, and proteins
- Alkaloids
- N-heteroaromatics (including pyrimidines, purines, porphyrins)
I hope it is clear that depth in any area cannot be attained (let alone hoped for) as the volume
of material for each topic listed could easily comprise an entire course on that topic. Indeed, I
have given some.
However, I anticipate a student well versed in Organic Chemistry will have little difficulty
keeping up with the slim text and the volume of additional materials provided.
Grading will be based upon one written
examination taken from the lecture notes, the readings at the end of each chapter and reading
material handed out in class. It is anticipated
that each student will present a lecture on some aspect of one of the broad areas listed.
Reading material handed out (by 25 September 2000):
- Liu, H. et al. "How is the Active Site of Enolase Organized to Catalyze Two Different
Reaction Steps" J. Am. Chem. Soc. 2000, 122, 6560.
- Cane, D. E. et al. "Biosynthesis of Vitamin B6: Origin of the Oxygen Atoms of
Pyridoxol Phosphate" J. Am. Chem. Soc. 2000, 122, 4213.
- Kushiro, T. et al. "Mutational Studies on Triterpene Synthases:Engineering Lupeol
Synthease into beta-Amyrin Synthase" J. Am. Chem. Soc. 2000, 122, 6816.
- Herrera, J. B. R. et al. "A Tyrosine-to-Threonine Mutation Converts Cycloartenol Synthase
to an Oxidosqualene Cyclase that Forms Lanosterol as Its Major Product" J. Am. Chem. Soc.
2000, 122, 6765.
- A copy of the Boyer Nobel Prize in Chemistry lecture (1977).
Questions and comments can be directed to Dalton's
Mail Box or dalton@astro.ocis.temple.edu.