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Cell-Permeable Peptides Containing Cycloalanine Residues.


ABSTRACT: We present here an efficient alternative to N-methylation for the purpose of morphing protein-binding peptides into more serum-stable and cell-permeable compounds. This involves the incorporation of a cycloalanine (CyAla) into a peptide in a way that avoids difficult coupling steps. We demonstrate the utility of this chemistry in creating a cell-permeable derivative of a high-affinity HIV Rev protein-binding peptide.

SUBMITTER: Wu H 

PROVIDER: S-EPMC5220248 | biostudies-literature | 2016 Oct

REPOSITORIES: biostudies-literature

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Cell-Permeable Peptides Containing Cycloalanine Residues.

Wu Hao H   Mousseau Guillaume G   Mediouni Sonia S   Valente Susana T ST   Kodadek Thomas T  

Angewandte Chemie (International ed. in English) 20160816 41


We present here an efficient alternative to N-methylation for the purpose of morphing protein-binding peptides into more serum-stable and cell-permeable compounds. This involves the incorporation of a cycloalanine (CyAla) into a peptide in a way that avoids difficult coupling steps. We demonstrate the utility of this chemistry in creating a cell-permeable derivative of a high-affinity HIV Rev protein-binding peptide. ...[more]

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