Student-Driven Design of Peptide Mimetics: Microwave-Assisted Synthesis of Peptoid Oligomers

An experiment for the undergraduate organic laboratory is described in which peptide mimetic oligomers called “peptoids” are built stepwise on a solid-phase resin. Students employ two modern strategies to facilitate rapid multistep syntheses: solid-phase techniques to obviate the need for intermedia...

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Bibliographic Details
Published in:Journal of chemical education 2011-07, Vol.88 (7), p.999-1001
Main Authors: Pohl, Nicola L. B, Kirshenbaum, Kent, Yoo, Barney, Schulz, Nathan, Zea, Corbin J, Streff, Jennifer M, Schwarz, Kimberly L
Format: Article
Language:English
Subjects:
Chemical reactions
College Science
College students
Cooperative Learning
Hands on Science
Irradiation
Laboratory Experiments
Oligomers
Organic Chemistry
Peptides
Radiation
Reagents
Science education
Science Experiments
Science Instruction
Solid phases
Students
Undergraduate Students
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Summary:An experiment for the undergraduate organic laboratory is described in which peptide mimetic oligomers called “peptoids” are built stepwise on a solid-phase resin. Students employ two modern strategies to facilitate rapid multistep syntheses: solid-phase techniques to obviate the need for intermediate purifications and microwave irradiation to enhance reaction rates. The modular reaction protocol is compatible with a vast array of reagents, allowing students to design unique oligomer sequences and to get a sense of modern drug-discovery processes. Students compare reactions performed both with and without microwave irradiation for a collaborative learning experience.
ISSN:0021-9584
1938-1328
DOI:10.1021/ed100763t