title: Oxime ligation in acetic acid: efficient synthesis of aminooxy-peptide conjugates.
abstract: Oxime ligation is a powerful tool in various bioconjugation strategies. Nevertheless, high reaction rates and quantitative yields are typically reported for aldehyde-derived compounds. In contrary, keto groups react much slower, with quantitative yields achieved at 5 h for low-molecular weight compounds and more than 15 h for polymers or dendrimers. In this communication, we report that oxime ligation proceeds rapidly with quantitative (>95%) conversion within 1.5-2 h in pure acetic acid. The practical utility of suggested technique is illustrated by the synthesis of peptide-steroid and peptide-polymer conjugates of model aminooxy-peptides. Copyright © 2016 European Peptide Society and John Wiley & Sons, Ltd.
authors.affiliation: Institute of Macromolecular Compounds, RAS, Bolshoy prospekt 31, Saint Petersburg, 199004, Russia.
authors.forename: Pavel S
authors.initials: PS
authors.lastname: Chelushkin
authors.affiliation: Institute of Macromolecular Compounds, RAS, Bolshoy prospekt 31, Saint Petersburg, 199004, Russia.
authors.forename: Maria V
authors.initials: MV
authors.lastname: Leko
authors.affiliation: Institute of Macromolecular Compounds, RAS, Bolshoy prospekt 31, Saint Petersburg, 199004, Russia.
authors.forename: Marina Yu
authors.initials: MY
authors.lastname: Dorosh
authors.affiliation: Institute of Macromolecular Compounds, RAS, Bolshoy prospekt 31, Saint Petersburg, 199004, Russia.
authors.forename: Sergey V
authors.initials: SV
authors.lastname: Burov
mesh_terms: D019342:Acetic Acid / Q000737:chemistry*; D000447:Aldehydes / Q000737:chemistry; D000588:Amines / Q000737:chemistry; D000595:Amino Acid Sequence; D010084:Oxidation-Reduction; D010091:Oximes / Q000737:chemistry*; D010455:Peptides / Q000737:chemistry*; D011205:Povidone / Q000737:chemistry; D013256:Steroids / Q000737:chemistry*; D013997:Time Factors
chemical_list: D000447:Aldehydes; D000588:Amines; D010091:Oximes; D010455:Peptides; D013256:Steroids; D011205:Povidone; D019342:Acetic Acid
keywords: aminooxy-peptides; oxime ligation; peptide-steroids conjugates; polymer-peptide conjugates