Rapid Multistep Synthesis of a Bioactive Peptidomimetic Oligomer for the Undergraduate Laboratory

Yeliz Utku ^[1] ; Abhinav Rohatgi ^[1] ; Barney Yoo ^[1] ; Kent Kirshenbaum ^[1] ; Ronald N. Zuckermann ^[2] ; Nicola L. Pohl
1. [1] New York University
  
  New York University
  
  Estados Unidos
2. [2] Lawrence Berkeley National Laboratory
  
  Lawrence Berkeley National Laboratory
  
  Estados Unidos
Localización: Journal of chemical education, ISSN 0021-9584, Vol. 87, Nº 6 (June), 2010, págs. 637-639
Idioma: inglés
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Resumen
- Peptidomimetic compounds are increasingly important in drug-discovery applications. We introduce the synthesis of an N-substituted glycine oligomer, a bioactive “peptoid” trimer. The six-step protocol is conducted on solid-phase resin, enabling the synthesis to be performed by undergraduate organic chemistry students. This synthesis lab was successfully completed within one 4-h session by second-year students. The procedures are relatively inexpensive and versatile, enabling modifications to generate a variety of oligomer sequences from commercially available reagents including bromoacetic acid and a diverse set of primary amines.