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1 Electronic Supplementary Information for: Squaric Acid Mediated Bioconjugation Expanded to Polymers Prepared by ATRP Tobias Steinbach, Frederik Wurm and Harm-Anton Klok * Ecole Polytechnique Fédérale de Lausanne (EPFL), Institut des Matériaux and Institut des Sciences et Ingénierie Chimiques, Laboratoire des Polymères, Bâtiment MXD, Station 12, CH-1015 Lausanne, Switzerland. * Corresponding author: Fax: + 41 21 693 5650; Tel: + 41 21 693 4866; E-mail: harm- [email protected] Electronic Supplementary Material (ESI) for Polymer Chemistry. This journal is © The Royal Society of Chemistry 2014

Squaric Acid Mediated Bioconjugation Expanded to Polymers ... · 1 Electronic Supplementary Information for: Squaric Acid Mediated Bioconjugation Expanded to Polymers Prepared by

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    Electronic Supplementary Information for:

    Squaric Acid Mediated Bioconjugation

    Expanded to Polymers Prepared by ATRP

    Tobias Steinbach, Frederik Wurm and Harm-Anton Klok*

    Ecole Polytechnique Fédérale de Lausanne (EPFL), Institut des Matériaux and Institut des

    Sciences et Ingénierie Chimiques, Laboratoire des Polymères, Bâtiment MXD, Station 12,

    CH-1015 Lausanne, Switzerland.

    * Corresponding author: Fax: + 41 21 693 5650; Tel: + 41 21 693 4866; E-mail: [email protected]

    Electronic Supplementary Material (ESI) for Polymer Chemistry.This journal is © The Royal Society of Chemistry 2014

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    Figure S1: 1H NMR spectrum of 3-ethoxy-4-(2-hydroxyethylamino)cyclobut-3-ene-1,2-dione (1) in DMSO-d6.

    Figure S2: 1H NMR spectrum of 2-(2-ethoxy-3,4-dioxocyclobut-1-enylamino)ethyl 2-bromo-2-methylpropanoate (2) in DMSO-d6.

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    Figure S3: 13C NMR spectrum of 2-(2-ethoxy-3,4-dioxocyclobut-1-enylamino)ethyl 2-bromo-2-methylpropanoate (2) in DMSO-d6.

    200 300 400 500 600 700 800

    O O

    O NH

    O

    O

    Br 2MH+

    MK+

    m/z

    334

    374

    668

    MH+

    Figure S4: ESI mass spectrum of 2-(2-ethoxy-3,4-dioxocyclobut-1-enylamino)ethyl 2-bromo-2-methylpropanoate (2).

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    Figure S5: 1H NMR spectrum of 3-(1,3-dihydroxypropan-2-ylamino)-4-ethoxycyclobut-3-ene-1,2-dione (3) in DMSO-d6.

    Figure S6: 13C NMR of 3-(1,3-dihydroxypropan-2-ylamino)-4-ethoxycyclobut-3-ene-1,2-dione (3) in DMSO-d6.

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    Figure S7: 1H NMR spectrum of 2-(2-ethoxy-3,4-dioxocyclobut-1-enylamino)propane-1,3-diyl bis(2-bromo-2-methylpropanoate) (4) in CDCl3.

    Figure S8: 13C NMR spectrum of 2-(2-ethoxy-3,4-dioxocyclobut-1-enylamino)propane-1,3-diyl bis(2-bromo-2-methylpropanoate) (4) in CDCl3.

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    Figure S9: ESI mass spectrum of 2-(2-ethoxy-3,4-dioxocyclobut-1-enylamino)propane-1,3-diyl bis(2-bromo-2-methylpropanoate) (4).

    Figure S10: 1H NMR spectrum of 3-(1,3-dihydroxy-2-(hydroxymethyl)propan-2-ylamino)-4-ethoxycyclobut-3-ene-1,2-dione (5) in DMSO-d6.

    MH+

    MK+

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    Figure S11: 13C NMR spectrum of 3-(1,3-dihydroxy-2-(hydroxymethyl)propan-2-ylamino)-4-ethoxycyclobut-3-ene-1,2-dione (5) in DMSO-d6.

    Figure S12: 1H NMR spectrum of 2-((2-bromo-2-methylpropanoyloxy)methyl)-2-(2-ethoxy-3,4-dioxocyclobut-1-enylamino)propane-1,3-diyl bis(2-bromo-2-methylpropanoate) (6) in CDCl3.

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    Figure S13: 13C NMR spectrum of 2-((2-bromo-2-methylpropanoyloxy)methyl)-2-(2-ethoxy-3,4-dioxocyclobut-1-enylamino)propane-1,3-diyl bis(2-bromo-2-methylpropanoate) (6) in CDCl3.

    Figure S14: ESI mass spectrum of 2-((2-bromo-2-methylpropanoyloxy)methyl)-2-(2-ethoxy-3,4-dioxocyclobut-1-enylamino)propane-1,3-diyl bis(2-bromo-2-methylpropanoate) (6).

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    Figure S15: 1H NMR spectrum of mid-functionalized PPEGMA # 2 in CDCl3.

    Figure S16: 1H NMR spectrum of three-arm PPEGMA #6 in CDCl3.

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