Solid-phase synthesis of diverse peptide tertiary amides by reductive amination

Pels, K.; Kodadek, T.

Acs Combinatorial Science 17(3): 152-155


ISSN/ISBN: 2156-8944
PMID: 25695359
DOI: 10.1021/acscombsci.5b00007
Accession: 058876172

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The synthesis of libraries of conformationally constrained peptide-like oligomers is an important goal in combinatorial chemistry. In this regard an attractive building block is the N-alkylated peptide, also known as a peptide tertiary amide (PTA). PTAs are conformationally constrained because of allylic 1,3 strain interactions. We report here an improved synthesis of these species on solid supports through the use of reductive amination chemistry using amino acid-terminated, bead-displayed oligomers and diverse aldehydes. The utility of this chemistry is demonstrated by the synthesis of a library of 10,000 mixed peptoid-PTA oligomers.