Peptoids (N-alkyl glycine oligomers) are peptidomimetics with unique features which make them a promising class of oligoamides for development within for example life sciences and materials. They are attracting an increasing interest, but substantial efforts have still not been devoted to greener synthetic methods. Thus, until now, the methods of synthesis of peptoids in solution or on solid-phase are based on the use of conventional solvents such as for example THF, DMF, NMP and CH2Cl2. In this communication, we will present the development and optimization of the first synthesis of peptoids in water or in aqueous micellar medium using Lipshutz’s surfactants. Peptoid oligomers with well-defined sequences up to the 6-mers were synthesized in solution-phase in the C-to-N or N-to-C direction using these methods. The scope and limitations of this first step towards sustainable peptoid synthesis will be illustrated by the synthesis of a selected natural peptide mimic.

Towards sustainable peptoid synthesis

ACS Spring 2022

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