This investigative case module was prepared as part of a BioQUEST faculty development workshop entitled Faculty Workshop: Implementing Investigative Cases and Technology in Biology and Chemistry at Center for Science Education in August 2004. The cases, resources, and implementation strategies were developed by participants for use with their own students. We invite you to adopt and adapt the following materials.

The BioQUEST Curriculum Consortium is committed to the reform of undergraduate biology instruction through an emphasis on engaging students in realistic scientific practices. This approach is sometimes characterized as an inquiry driven approach and is captured in BioQUEST's three P's (problem-posing, problem-solving, and peer-persuasion). As part of this workshop groups of faculty were encouraged to initiate innovative curricular projects. We are sharing these works in progress in the hope that they will stimulate further exploration, collaboration and development. Please see the following links for additional information:

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Investigative Cases
   
The Case: Drugland

Cathy, who is three months pregnant is complaining to her friend Kelly about morning sickness:

"Oah, Kelly, I don't know what they call it morning sickness, because it actually lasts all day long. I am about to order a drug, called Thalomide over the internet, that is available without prescription in "Drugland" but not in the US."

"Oh, no!", screams Kelly horrified. "Haven't you heard the story about it? It used to be available in Europe in the 60's but they had to remove it from the market because of the birth defects it created when pregnant women took it. They say it's because it contains two molecules identical except for one thing: one is right handed, the other one is left handed and one causes birth defect but not the other one! I am sorry for you, Cathy, but you cannot take that."

Cathy drops the mouse of the computer and replies, puzzled:
"What is that all about?"

Case Author:
Anne Gaquere State University of West Georgia

Case Analysis


What is Thalomide?

What are chiral molecules?

How does chirality in molecules affect biological systems?

How are chiral molecules prepared, isolated and evaluated?

What are birth defects created by Thalidomide and what are the mechanisms?

Why did it occur mainly in Europe?

What is the role of FDA?

Option: Include a know / need to know chart like the one below:

What do you know?
What do you need to know?
   

Learning Goals

Goal(s)

Students would learn about stereochemistry, its importance in biological systems and the importance of optical purity in drug design and manufacture.

Standards

 

Investigations and Activities

This case can be connected to a laboratory activity where students have different solutions of chiral compounds under the form of a racemic mixture, of the pure enantiomers and of a non-racemic mixture of them. They would measure and record the optical activity of all these solutions.

 

Resources

Organic chemistry textbook

Biochemistry textbook

Merck index

http://www.celgene.com/thalomid/

http://www.chm.bris.ac.uk/motm/thalidomide/start.html

http://www.chemsoc.org/chembytes/ezine/2001/stephens_nov01.htm

http://www.fda.gov/cder/news/thalinfo/thalidomide.htm

Students will usually obtain additional references or resources
to help answer or explore their questions.

Special Data Items

1. thalidomide.jpg

 

Student Products

The students, working in groups of four, are to turn in a homework assignment, which should be a one-page typed, printed paper and which should clearly answer the following 7 questions:
What is Thalomide?

What are chiral molecules?

How does chirality in molecules affect biological systems?

How are chiral molecules prepared, isolated and evaluated?

What are birth defects created by Thalidomide and what are the mechanisms?

Why did it occur mainly in Europe?

What is the role of FDA?

Then after an in class collegial review of some of the answers, they would have to write a pamphlet to be sent to women health centers in poor areas where pregnant women may be incline to order cheaper (or not prescribed) drugs over the internet.

Assessment and Evaluation Plan

The first homework is made of 7 questions for which they receive 7 points: 1 point per right, accurate and concise answer. At the end of the session, using the Personal Response System, I would ask 3 questions concerning the case/chapter under the form of a multiple choice question quiz for 3 more points. The pamphlet would count for an extra 10 points.

 

Implementation

At the end of a session, I will pull up a slide with the case and I will ask the students to answer 7 questions (see details above)

Once in class, they turn in their paper. Then I will randomly select 2 answers per question from different papers. We will discuss together for 15 to 20 minutes the quality or accuracy of these answers (this is for an 1hour and 15 minute class). Then I will start a traditional lecture about stereochemistry.

At the end of the session, using the Personal Response System, I would ask 3 questions concerning the case/chapter under the form of a multiple choice question quiz.

The final pamphlets will be collected during the next class meeting.

Course name:
Organic Chemistry part 1 lecture
Likely sequence in syllabus:
chapter 9: Stereochemistry
Time during term:
half way through the semester
Duration:
as a homework between 2 sessions
Setting:
lecture
Students in course:
86
Collaborative elements:
stereoisomerism: chapters 3 and 4, laboratory experiment about stereochemistry
Additional notes:
used to introduce the chapter about stereochemistry

 

Credits


http://images.google.com/images?q=tbn:j7XMu-8z5DwJ:www.uyseg.org/catalysis/asymmetric/images/asymm7.gif
http://www.celgene.com/thalomid/
http://www.chm.bris.ac.uk/motm/thalidomide/start.html
http://www.chemsoc.org/chembytes/ezine/2001/stephens_nov01.html
http://www.fda.gov/cder/news/thalinfo/thalidomide.htm

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