title: Comb Poly(Oligo(2-Ethyl-2-Oxazoline)Methacrylate)-Peptide Conjugates Prepared by Aqueous Cu(0)-Mediated Polymerization and Reductive Amination.
abstract: The controlled synthesis of poly(oligo(2-ethyl-2-oxazoline)methacrylate) (P(OEtOxMA)) polymers by Cu(0)-mediated polymerization in water/methanol mixtures is reported. Utilizing an acetal protected aldehyde initiator for the polymerization, well-defined polymers are synthesized (>99% conversion, Ð < 1.25) with subsequent postpolymerization deprotection resulting in α-aldehyde end group containing comb polymers. These P(OEtOxMA) are subsequently site-specifically conjugated, via reductive amination, to a dipeptide (NH2-Gly-Tyr-COOH) as a model peptide, prior to conjugation to the functional peptide oxytocin. The resulting oxytocin conjugates are evaluated in comparison to poly(oligo(ethylene glycol) methyl ether methacrylate) combs synthesized in the same manner for potential effects on thermal stability in comparison to the native peptide.
authors.affiliation: Chemistry Department, University of Warwick, Coventry, CV4 7AL, UK.
authors.forename: Jennifer
authors.initials: J
authors.lastname: Collins
authors.affiliation: Chemistry Department, University of Warwick, Coventry, CV4 7AL, UK.
authors.forename: Sacha J
authors.initials: SJ
authors.lastname: Wallis
authors.affiliation: Chemistry Department, University of Warwick, Coventry, CV4 7AL, UK.
authors.forename: Alexandre
authors.initials: A
authors.lastname: Simula
authors.affiliation: ARC Centre of Excellence in Convergent Bio-Nano Science & Technology, Monash Institute of Pharmaceutical Sciences, Monash University, Parkville, VIC, 3052, Australia.
authors.forename: Michael R
authors.initials: MR
authors.lastname: Whittaker
authors.affiliation: Monash Institute of Pharmaceutical Sciences, Monash University, Parkville, VIC, 3052, Australia.
authors.forename: Michelle P
authors.initials: MP
authors.lastname: McIntosh
authors.affiliation: Chemistry Department, University of Warwick, Coventry, CV4 7AL, UK.|ARC Centre of Excellence in Convergent Bio-Nano Science & Technology, Monash Institute of Pharmaceutical Sciences, Monash University, Parkville, VIC, 3052, Australia.
authors.forename: Paul
authors.initials: P
authors.lastname: Wilson
authors.affiliation: Chemistry Department, University of Warwick, Coventry, CV4 7AL, UK.|ARC Centre of Excellence in Convergent Bio-Nano Science & Technology, Monash Institute of Pharmaceutical Sciences, Monash University, Parkville, VIC, 3052, Australia.
authors.forename: Thomas P
authors.initials: TP
authors.lastname: Davis
authors.affiliation: Chemistry Department, University of Warwick, Coventry, CV4 7AL, UK.|ARC Centre of Excellence in Convergent Bio-Nano Science & Technology, Monash Institute of Pharmaceutical Sciences, Monash University, Parkville, VIC, 3052, Australia.
authors.forename: David M
authors.initials: DM
authors.lastname: Haddleton
authors.affiliation: Chemistry Department, University of Warwick, Coventry, CV4 7AL, UK.|ARC Centre of Excellence in Convergent Bio-Nano Science & Technology, Monash Institute of Pharmaceutical Sciences, Monash University, Parkville, VIC, 3052, Australia.
authors.forename: Kristian
authors.initials: K
authors.lastname: Kempe
mesh_terms: D000586:Amination; D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry; D003300:Copper / Q000737:chemistry*; D000432:Methanol / Q000737:chemistry; D015394:Molecular Structure; D010455:Peptides / Q000737:chemistry*; D058105:Polymerization; D011109:Polymethacrylic Acids / Q000737:chemistry*; D014867:Water / Q000737:chemistry*
chemical_list: D000588:Amines; D010455:Peptides; D011109:Polymethacrylic Acids; D014867:Water; D003300:Copper; D000432:Methanol
keywords: controlled radical polymerization; oxytocin; poly(2-oxazoline); polymer-peptide conjugation; reductive amination