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, (Eth) < 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.
| Original language | English |
|---|---|
| Article number | 1600534 |
| Number of pages | 7 |
| Journal | Macromolecular Rapid Communications |
| Volume | 38 |
| Issue number | 2 |
| DOIs | |
| Publication status | Published - 1 Jan 2017 |
Keywords
- Controlled radical polymerization
- Oxytocin
- Poly(2-oxazoline)
- Polymer-peptide conjugation
- Reductive amination
Cite this
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Comb poly(oligo(2-ethyl-2-oxazoline)methacrylate)-peptide conjugates prepared by aqueous Cu(0)-mediated polymerization and reductive amination. / Collins, Jennifer; Wallis, Sacha J.; Simula, Alexandre; Whittaker, Michael R.; McIntosh, Michelle P.; Wilson, Paul; Davis, Thomas P.; Haddleton, David M.; Kempe, Kristian.
In: Macromolecular Rapid Communications, Vol. 38, No. 2, 1600534, 01.01.2017.Research output: Contribution to journal › Article › Research › peer-review
TY - JOUR
T1 - Comb poly(oligo(2-ethyl-2-oxazoline)methacrylate)-peptide conjugates prepared by aqueous Cu(0)-mediated polymerization and reductive amination
AU - Collins, Jennifer
AU - Wallis, Sacha J.
AU - Simula, Alexandre
AU - Whittaker, Michael R.
AU - McIntosh, Michelle P.
AU - Wilson, Paul
AU - Davis, Thomas P.
AU - Haddleton, David M.
AU - Kempe, Kristian
PY - 2017/1/1
Y1 - 2017/1/1
N2 - 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, (Eth) < 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.
AB - 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, (Eth) < 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.
KW - Controlled radical polymerization
KW - Oxytocin
KW - Poly(2-oxazoline)
KW - Polymer-peptide conjugation
KW - Reductive amination
UR - http://www.scopus.com/inward/record.url?scp=85002543562&partnerID=8YFLogxK
U2 - 10.1002/marc.201600534
DO - 10.1002/marc.201600534
M3 - Article
VL - 38
JO - Macromolecular Rapid Communications
JF - Macromolecular Rapid Communications
SN - 1022-1336
IS - 2
M1 - 1600534
ER -