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

• Published in: Journal of chemical education Vol. 88; no. 7; pp. 999 - 1001
• Main Authors: Pohl, Nicola L. B, Kirshenbaum, Kent, Yoo, Barney, Schulz, Nathan, Zea, Corbin J, Streff, Jennifer M, Schwarz, Kimberly L
• Format: Journal Article
• Language: English
• Published: Easton American Chemical Society and Division of Chemical Education, Inc 01.07.2011; Division of Chemical Education, Inc and ACS Publications Division of the American Chemical Society; American Chemical Society
• 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; Hands-On Learning/Manipulatives; Medicinal Chemistry; NMR Spectroscopy; Nucleophilic Substitution; Laboratory Instruction; Proteins/Peptides; IR Spectroscopy; Second-Year Undergraduate; Amides; Organic Chemistry
• ISSN: 0021-9584; 1938-1328
• DOI: 10.1021/ed100763t

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.