title: Chemoselective fragment condensation between peptide and peptidomimetic oligomers.
abstract: We report the first example of chemoselective fragment condensation, through native amide bond formation, between peptoid and peptide oligomers. Peptoid oligomers bearing C-terminal salicylaldehyde esters were synthesized and ligated to peptides containing N-terminal serine or threonine residues. We investigate the ligation efficiency of peptoid oligomers varying in length, sequence, and C-terminal steric bulk. These protocols enhance accessibility of structurally complex peptoid-peptide hybrids and will facilitate the design new semi-synthetic proteins with unique attributes.
authors.affiliation: Department of Chemistry, New York University, New York, New York 10003, USA.
authors.forename: Paul M
authors.initials: PM
authors.lastname: Levine
authors.forename: Timothy W
authors.initials: TW
authors.lastname: Craven
authors.forename: Richard
authors.initials: R
authors.lastname: Bonneau
authors.forename: Kent
authors.initials: K
authors.lastname: Kirshenbaum
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D000577:Amides / Q000737:chemistry; D010455:Peptides / Q000138:chemical synthesis / Q000737:chemistry*; D057786:Peptidomimetics / Q000138:chemical synthesis / Q000737:chemistry*; D034444:Peptoids / Q000138:chemical synthesis / Q000737:chemistry*; D012694:Serine / Q000737:chemistry; D013912:Threonine / Q000737:chemistry
chemical_list: D000447:Aldehydes; D000577:Amides; D010455:Peptides; D057786:Peptidomimetics; D034444:Peptoids; C013243:salicylaldehyde; D013912:Threonine; D012694:Serine