Title: Combinatorial Thinking in CHM236 Organic Chemistry Laboratory
1Combinatorial Thinking in CHM236 Organic
Chemistry Laboratory
- Dr. Sujatha Krishnaswamy
- Chemistry Faculty
- Chandler Gilbert Community College
2- Experiments that use combinatorial chemistry as
applied to modern drug discovery - Suitable for one year CHM235/236 organic
chemistry curriculum
3What is Combinatorial Chemistry?
- Is an approach that provides efficient synthesis
of a large collection of molecules - Screening of libraries of related compounds to
isolate the molecule of desirable property - Used in both academia and industries to generate
huge libraries of compounds that have important
biological properties
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5Advantages of Combinatorial Synthesis
- Perform fewer reactions and fewer tests to
identify the biological activity of a winning
molecule - Use synthetic organic chemistry to generate many
compounds in a single or parallel batch
6Main Features
- The type of molecule that comprises the library
- All compounds are related to one another built
from common building blocks - Each molecule is comprised of a unique
combination or sequence
7Synthesis of Fruity Esters
- Assigned Problem
- Use combinatorial chemistry to synthesize an
ester - of an assigned scent.
8Generation of library of molecules Mix
combinations of alcohols and carboxylic acids to
solve the assigned problem
- CH3OH A1
- CH3CH2OH A2
- 1-pentanol A3
- 3-methylbutanol A4
- 1-octanol A5
- Butanoic acid C1
- Propanoic acid C2
- Acetic acid C3
Possible combinations A1C1, A1C2,
A1C3. Deconvolution of library checking the
odor of esters
9Preparation of Hydrazones and Discovery of an
Antibiotic Compound using Combinatorial techniques
Synthesis of Hydrazones
- Two component system
- High yield
- No workup
- Color change
- Solution phase
10Generation of Libraries
11Deconvolution (Encoding) of Hydrazone Libraries
12Synthesis of Sulfanilamide Derivatives and
Bacterial Testing
Reaction of p-Acetamidobenzenesulfonyl chloride
with an amine
13Design of Library
Amines
14Possible applications..
- Ability to kill bacterial cells
- Electrical conductivity
- A desired color
- A desired odor
- A desired pH change
What distinguishes combinatorial chemistry?
15Why combinatorial principles in organic chemistry?
- Fast becoming part of college curriculum
- Readily adaptable
- Discussion of mechanism, alternate synthesis and
structure-reactivity relationships part of one
year organic chemistry curriculum - Examples that combine chemistry and biology
- Demonstrates the usefulness of multidisciplinary
approaches to solve complex problems