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Issue 17, 2018
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Maleimide end-functionalized poly(2-oxazoline)s by the functional initiator route: synthesis and (bio)conjugation

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Abstract

The synthesis of poly(2-ethyl-2-oxazoline)s with a maleimide group at the α chain end was carried out from new sulfonate ester initiators bearing a furan-protected maleimide group. The conditions of the polymerization were optimized for 50 °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 < Mn < 12 000 g mol−1) with narrow dispersity (Đ < 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 1H 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.

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

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Publication details

The article was received on 30 Jan 2018, accepted on 22 Feb 2018 and first published on 05 Mar 2018


Article type: Paper
DOI: 10.1039/C8RA00948A
Citation: RSC Adv., 2018,8, 9471-9479
  • Open access: Creative Commons BY-NC license
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    Maleimide end-functionalized poly(2-oxazoline)s by the functional initiator route: synthesis and (bio)conjugation

    G. Gil Alvaradejo, M. Glassner, R. Hoogenboom and G. Delaittre, RSC Adv., 2018, 8, 9471
    DOI: 10.1039/C8RA00948A

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