Incorporation of Heterocycles into the Backbone of Peptoids to Generate Diverse Peptoid-Inspired One Bead One Compound Libraries

Department of Chemistry, The Scripps Research Institute, Scripps Florida , Jupiter, Florida 33458, United States.
ACS combinatorial science 02/2012; 14(3):164-9. DOI: 10.1021/co200195t
Source: PubMed


Combinatorial libraries of peptoids (oligo-N-substituted glycines) have proven to be useful sources of protein ligands. Each unit of the peptoid oligomer is derived from 2-haloacetic acid and a primary amine. To increase the chemical diversity available in peptoid libraries, we demonstrate here that heterocyclic halomethyl carboxylic acids can be employed as backbone building blocks in the synthesis of peptoid-based oligomers. Optimized conditions are reported that allow the creation of large, high quality combinatorial libraries containing these units.

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    • "However, this often requires large and chemically diverse compound libraries. In recent years, peptoid synthesis has been established on solid phase to allow for the combinatorial synthesis of highly diverse libraries of peptoids [14,16,17,25,26,27,28,29]. The synthesis of diverse peptoid scaffolds is usually performed by the so called submonomer approach through microwave-assisted amide bond formation and subsequent nucleophilic substitution with primary amines or via heterocyclic halomethyl carboxylic building blocks [25]. "
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