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Support Materials:
- Goal:
To define and characterize the properties of small molecules, continued...
- Objectives:
Students will be able to...
- identify chiral carbon atoms, given the structural formula for a compound.
Comprehension: Examples -
coniine,
nicotine,
methyl jasmonate, fenfluramine, thalidomide.
Applications:
fen-phen (the
"fen" part is short for fenfluramine, a drug that has a single chiral
center. One enantiomer is an appetite suppressant, the other causes
drowsiness. The "phen" part, short for phentermine, was added as a
stimulant. Fen-phen, which included a racemic mixture of fen, was given for
weight loss, but it was banned after incidence of primary pulmonary
hypertension and heart valve damage. Some argued that the use of a racemate
was causing these adverse effects, or perhaps it was the phentermine. The
"correct" enantiomer of fen (the diet form) was purified and marketed (under
the name Redux). Did this solve the problem? (Do you recall the
answer from class?)
Thalidomide
- an example of a drug that will racemize in the blood stream. One of the
great
drug tragedies from the 60's.
Amino acids, and sugars (polyhydroxylated aldehydes or ketones) are also
examples of chiral compounds. Helpful hint: Carbon
atoms with multiple bonds are never chiral.
- identify structural formulas of amino acids by full name, 3-letter code,
and 1-letter code.
Knowledge: Learn to recognize the structures of the 20 standard amino acids
using an online game.
Click here, then select "Amino Acids Game". (Brought to you by
Interactive Concepts in Biochemistry
by Wiley Publishers.)
- categorize the side chain structures of amino acids at physiological pH as
nonpolar, polar neutral, polar positive, or polar
negative.
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