IC006 Chemistry of Steroids

Faculty of Science
Spring 2006
Extent and Intensity
0/0. 1 credit(s). Type of Completion: k (colloquium).
Guaranteed by
prof. RNDr. Radek Marek, Ph.D.
Chemistry Section – Faculty of Science
Contact Person: prof. RNDr. Radek Marek, Ph.D.
Course Enrolment Limitations
The course is offered to students of any study field.
Course objectives (in Czech)
A lipid is defined as a naturally occurring organic compound, which is insoluble in water but soluble in nonpolar organic solvents [1a]. Thus biological lipids create a chemically diverse group of compounds, with equally diverse biological functions. Fats and oils are the principal stored forms of energy in many organisms, whereas phospholipids and sterols play crucial roles as structural lipids in membranes [2a]. Yet another group of lipids, although present in relatively small quantities, has essential biological activities. This group includes a large amount of isoprenoids and hundreds of steroids [2b]. Generally, a steroid is a compound containing a particular four-ring molecular structure, called cyclopentanoperhydrophenantrene ring system. Steroids differ from one another by side chain structures, substituents, and additional rings [3]. Many steroids may be named as derivatives of cholestane, the structure of which is shown in the Scheme [1b]. Steroids are found in almost all types of living systems [1b]. The range of steroids is diverse, including digitalis, several forms of vitamin D, and the bile acids. In animals many steroids play crucial roles as hormones. These include the male sex hormone testosterone and the female sex hormones estrogen and progesterone. The steroid hormones secreted by the adrenal cortex include cortisone, cortisol, and aldosterone [3]. Both naturally occurring and synthetic steroids and their derivatives have found wide use as pharmaceuticals [1b]. During the course some important features of chemistry of steroids, such as their structure, physical and chemical properties, biosynthesis, metabolism, use in synthetics, structural analysis, and applications will be covered. References: 1a Fessenden, R.J.; Fessenden, J.S. Organic Chemistry. 5th Ed. Brooks/Cole Publishing Company, Pacific Grove, California (1994) pp. 941. 1b Fessenden, R.J.; Fessenden, J.S. Organic Chemistry. 5th Ed. Brooks/Cole Publishing Company, Pacific Grove, California (1994) pp. 952. 2a Lehninger, A.L.; Nelson, D.L.; Cox, M.M. Principles of Biochemistry. 2nd Ed.Worth Publishers, New York (1993) pp. 240. 2b Lehninger, A.L.; Nelson, D.L.; Cox, M.M. Principles of Biochemistry. 2nd Ed.Worth Publishers, New York (1993) pp. 256. 3 http://columbia.thefreedictionary.com/steroids, 28.02.2006.
Language of instruction
English
Further comments (probably available only in Czech)
Information on the extent and intensity of the course: 8 lectures.
Teacher's information
http://www.chemi.muni.cz/nmr/radek/steroids.pdf
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