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Maleimide end-functionalized poly(2-oxazoline)s by the functional initiator route : synthesis and (bio) conjugation

(2018) RSC ADVANCES. 8(17). p.9471-9479
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Abstract
The synthesis of poly(2-ethyl-2-oxazoline)s with a maleimide group at the a chain end was carried out from new sultanate ester initiators bearing a furan-protected maleimide group. The conditions of the polymerization were optimized for 50 degrees C using conventional heating (in contrast to microwave irradiation) to counteract the thermal lability of the cycloadduct introduced to protect the maleimide double bond. At this temperature, a tosylate variant was found to be unable to initiate the polymerization after several days. The controlled polymerization of 2-ethyl-2-oxazoline with a nosylate derivative was, however, successful as shown by kinetic experiments monitored by gas chromatography (GC) and size-exclusion chromatography (SEC). Poly(2-ethyl-oxazoline)s of various molar masses (4500 < M-n < 12 000 g mol(-1)) with narrow dispersity (D < 1.2) were obtained. The stability of the protected maleimide functionality during the polymerization, its deprotection, and the reactivity of the deprotected end group by coupling with a model thiol molecule were proven by H-1 NMR spectroscopy and electrospray ionization mass spectrometry (ESI-MS). Finally, the conjugation of maleimide-functionalized poly(2-oxazoline) to a model protein (bovine serum albumin) was demonstrated by gel electrophoresis and MALDI-ToF mass spectrometry.
Keywords
RING-OPENING POLYMERIZATION, POLY(ETHYLENE GLYCOL), ISOMERIZATION, POLYMERIZATION, RADICAL POLYMERIZATION, POLYETHYLENE-GLYCOL, CLICK, REACTION, DRUG-DELIVERY, CHEMISTRY, POLYMERS, 2-METHYL-2-OXAZOLINE

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Citation

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Chicago
Alvaradejo, Gabriela Gil, Mathias Glassner, Richard Hoogenboom, and Guillaume Delaittre. 2018. “Maleimide End-functionalized Poly(2-oxazoline)s by the Functional Initiator Route : Synthesis and (bio) Conjugation.” Rsc Advances 8 (17): 9471–9479.
APA
Alvaradejo, G. G., Glassner, M., Hoogenboom, R., & Delaittre, G. (2018). Maleimide end-functionalized poly(2-oxazoline)s by the functional initiator route : synthesis and (bio) conjugation. RSC ADVANCES, 8(17), 9471–9479.
Vancouver
1.
Alvaradejo GG, Glassner M, Hoogenboom R, Delaittre G. Maleimide end-functionalized poly(2-oxazoline)s by the functional initiator route : synthesis and (bio) conjugation. RSC ADVANCES. 2018;8(17):9471–9.
MLA
Alvaradejo, Gabriela Gil et al. “Maleimide End-functionalized Poly(2-oxazoline)s by the Functional Initiator Route : Synthesis and (bio) Conjugation.” RSC ADVANCES 8.17 (2018): 9471–9479. Print.
@article{8600124,
  abstract     = {The synthesis of poly(2-ethyl-2-oxazoline)s with a maleimide group at the a chain end was carried out from new sultanate ester initiators bearing a furan-protected maleimide group. The conditions of the polymerization were optimized for 50 degrees C using conventional heating (in contrast to microwave irradiation) to counteract the thermal lability of the cycloadduct introduced to protect the maleimide double bond. At this temperature, a tosylate variant was found to be unable to initiate the polymerization after several days. The controlled polymerization of 2-ethyl-2-oxazoline with a nosylate derivative was, however, successful as shown by kinetic experiments monitored by gas chromatography (GC) and size-exclusion chromatography (SEC). Poly(2-ethyl-oxazoline)s of various molar masses (4500 {\textlangle} M-n {\textlangle} 12 000 g mol(-1)) with narrow dispersity (D {\textlangle} 1.2) were obtained. The stability of the protected maleimide functionality during the polymerization, its deprotection, and the reactivity of the deprotected end group by coupling with a model thiol molecule were proven by H-1 NMR spectroscopy and electrospray ionization mass spectrometry (ESI-MS). Finally, the conjugation of maleimide-functionalized poly(2-oxazoline) to a model protein (bovine serum albumin) was demonstrated by gel electrophoresis and MALDI-ToF mass spectrometry.},
  author       = {Alvaradejo, Gabriela Gil and Glassner, Mathias and Hoogenboom, Richard and Delaittre, Guillaume},
  issn         = {2046-2069},
  journal      = {RSC ADVANCES},
  language     = {eng},
  number       = {17},
  pages        = {9471--9479},
  title        = {Maleimide end-functionalized poly(2-oxazoline)s by the functional initiator route : synthesis and (bio) conjugation},
  url          = {http://dx.doi.org/10.1039/c8ra00948a},
  volume       = {8},
  year         = {2018},
}

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