title: C-Terminally modified peptides via cleavage of the HMBA linker by O-, N- or S-nucleophiles.
abstract: A large variety of C-terminally modified peptides was obtained by nucleophilic cleavage of the ester bond in solid phase linked peptide esters of 4-hydroxymethyl benzamide (HMBA). The developed methods provided peptides, C-terminally functionalized as esters, amides and thioesters, with high purity directly from the resin in a single reaction step. A comprehensive screening of the reaction conditions and scope for nucleophilic cleavage of peptides from the HMBA linker was performed.
authors.affiliation: Center for Evolutionary Chemical Biology, Department of Chemistry University of Copenhagen, Universitetsparken 5, 2100 Copenhagen, Denmark. meldal@nano.ku.dk.
authors.forename: J
authors.initials: J
authors.lastname: Hansen
authors.affiliation: Center for Evolutionary Chemical Biology, Department of Chemistry University of Copenhagen, Universitetsparken 5, 2100 Copenhagen, Denmark. meldal@nano.ku.dk.
authors.forename: F
authors.initials: F
authors.lastname: Diness
authors.affiliation: Center for Evolutionary Chemical Biology, Department of Chemistry University of Copenhagen, Universitetsparken 5, 2100 Copenhagen, Denmark. meldal@nano.ku.dk.
authors.forename: M
authors.initials: M
authors.lastname: Meldal
mesh_terms: D001549:Benzamides / Q000737:chemistry*; D004952:Esters / Q000737:chemistry; D008968:Molecular Conformation; D010455:Peptides / Q000737:chemistry*
chemical_list: C000612080:4-hydroxymethyl benzamide; D001549:Benzamides; D004952:Esters; D010455:Peptides