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Michael Addition of Thiol Compounds on ω-Maleate Poly(ethylene oxide)s: Model Study for the “Site-Specific” Modification of Proteins

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Abstract

In this study, we successfully synthesized ω-maleate poly(ethylene oxide)s (PEOs) as the modifier for proteins through the thiol-ene Michael addition reaction. Both α-azido-ω-maleate PEO and α-t-butoxy-ω-maleate PEO were obtained from the reaction of ‘living’ polymeric alkoxides with maleic anhydride (over 98 mol%). To examine their availability as one of basic matrices for the thiol-ene Michael addition, model compounds as the precursors of protein carrying the thiol group such as thioacetic acid, cysteamine, and cysteine were employed. Their addition on the maleate group was over 98 mol% under sonication or ultraviolet (UV) irradiation. The acidic condition appeared to affect to yield a diastereomeric mixture. All the PEOs carrying the ω-maleate group appeared to be applied for the efficient modifiers in the “site-specific” PEGylation of peptides or proteins. All the functionalized PEOs including ω-succinate PEO were characterized by a combination of size exclusion chromatographic (SEC), 1H nuclear magnetic resonance (NMR), and Fourier transform-infrared (FT-IR) spectroscopic analyses.

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Authors and Affiliations

  1. Department of Chemistry, Kyung Hee University, Seoul, 02453, Korea

    Hong Bin Yoon, Youra Lee, Donghwa Seo, Saeon Kim, Abu B. Siddique, Jae Yeol Lee, Jeewoo Lim & Jungahn Kim

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  1. Hong Bin Yoon
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  2. Youra Lee
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  3. Donghwa Seo
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  4. Saeon Kim
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  5. Abu B. Siddique
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  6. Jae Yeol Lee
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  7. Jeewoo Lim
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  8. Jungahn Kim
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Correspondence to Jeewoo Lim or Jungahn Kim.

Additional information

Acknowledgments: This work was funded by the Program (20160681) of Dongnam Chemical Co.

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Yoon, H.B., Lee, Y., Seo, D. et al. Michael Addition of Thiol Compounds on ω-Maleate Poly(ethylene oxide)s: Model Study for the “Site-Specific” Modification of Proteins. Macromol. Res. 26, 194–203 (2018). https://doi.org/10.1007/s13233-018-6021-4

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  • DOI: https://doi.org/10.1007/s13233-018-6021-4

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