title: 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.
authors.affiliation: Department of Chemistry and Cancer Biology, The Scripps Research Institute, 130 Scripps Way, Jupiter, FL, 33458, USA.
authors.forename: Hao
authors.identifier: 0000-0001-9487-5331
authors.initials: H
authors.lastname: Wu
authors.affiliation: Department of Immunology and Microbial Sciences, The Scripps Research Institute, 130 Scripps Way, Jupiter, FL, 33458, USA.
authors.forename: Guillaume
authors.initials: G
authors.lastname: Mousseau
authors.affiliation: Department of Immunology and Microbial Sciences, The Scripps Research Institute, 130 Scripps Way, Jupiter, FL, 33458, USA.
authors.forename: Sonia
authors.initials: S
authors.lastname: Mediouni
authors.affiliation: Department of Immunology and Microbial Sciences, The Scripps Research Institute, 130 Scripps Way, Jupiter, FL, 33458, USA.
authors.forename: Susana T
authors.initials: ST
authors.lastname: Valente
authors.affiliation: Department of Chemistry and Cancer Biology, The Scripps Research Institute, 130 Scripps Way, Jupiter, FL, 33458, USA. kodadek@scripps.edu.
authors.forename: Thomas
authors.identifier: 0000-0003-1930-4795
authors.initials: T
authors.lastname: Kodadek
mesh_terms: D000409:Alanine / Q000737:chemistry*; D057846:Cell-Penetrating Peptides / Q000737:chemistry*; D006367:HeLa Cells; D006801:Humans; D008968:Molecular Conformation
chemical_list: D057846:Cell-Penetrating Peptides; D000409:Alanine
keywords: HIV Rev; antiviral; cell permeability; cyclic peptides; peptidomimetics