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5-Hydroxy-pyrrolone based building blocks as maleimide alternatives for protein bioconjugation and single-site multi-functionalization

(2021) CHEMICAL SCIENCE. 12(14). p.5246-5252
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Abstract
Recent dramatic expansion in potential uses of protein conjugates has fueled the development of a wide range of protein modification methods; however, the desirable single-site multi-functionalization of proteins has remained a particularly intransigent challenge. Herein, we present the application of 5-hydroxy-1,5-dihydro-2H-pyrrol-2-ones (5HP2Os) as advantageous alternatives to widely used maleimides for the chemo- and site-selective labeling of cysteine residues within proteins. A variety of 5HP2O building blocks have been synthesized using a one-pot photooxidation reaction starting from simple and readily accessible furans and using visible light and oxygen. These novel reagents display excellent cysteine selectivity and also yield thiol conjugates with superior stability. 5HP2O building blocks offer a unique opportunity to introduce multiple new functionalities into a protein at a single site and in a single step, thus, significantly enhancing the resultant conjugate's properties.
Keywords
General Chemistry, REAGENTS, CONJUGATION, STABILITY, TYROSINE, FURANS

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Citation

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MLA
De Geyter, Ewout, et al. “5-Hydroxy-Pyrrolone Based Building Blocks as Maleimide Alternatives for Protein Bioconjugation and Single-Site Multi-Functionalization.” CHEMICAL SCIENCE, vol. 12, no. 14, 2021, pp. 5246–52, doi:10.1039/d0sc05881e.
APA
De Geyter, E., Antonatou, E., Kalaitzakis, D., Smolen, S., Iyer, A., Tack, L., … Madder, A. (2021). 5-Hydroxy-pyrrolone based building blocks as maleimide alternatives for protein bioconjugation and single-site multi-functionalization. CHEMICAL SCIENCE, 12(14), 5246–5252. https://doi.org/10.1039/d0sc05881e
Chicago author-date
De Geyter, Ewout, Eirini Antonatou, Dimitris Kalaitzakis, Sabina Smolen, Abhishek Iyer, Laure Tack, Emiel Ongenae, Georgios Vassilikogiannakis, and Annemieke Madder. 2021. “5-Hydroxy-Pyrrolone Based Building Blocks as Maleimide Alternatives for Protein Bioconjugation and Single-Site Multi-Functionalization.” CHEMICAL SCIENCE 12 (14): 5246–52. https://doi.org/10.1039/d0sc05881e.
Chicago author-date (all authors)
De Geyter, Ewout, Eirini Antonatou, Dimitris Kalaitzakis, Sabina Smolen, Abhishek Iyer, Laure Tack, Emiel Ongenae, Georgios Vassilikogiannakis, and Annemieke Madder. 2021. “5-Hydroxy-Pyrrolone Based Building Blocks as Maleimide Alternatives for Protein Bioconjugation and Single-Site Multi-Functionalization.” CHEMICAL SCIENCE 12 (14): 5246–5252. doi:10.1039/d0sc05881e.
Vancouver
1.
De Geyter E, Antonatou E, Kalaitzakis D, Smolen S, Iyer A, Tack L, et al. 5-Hydroxy-pyrrolone based building blocks as maleimide alternatives for protein bioconjugation and single-site multi-functionalization. CHEMICAL SCIENCE. 2021;12(14):5246–52.
IEEE
[1]
E. De Geyter et al., “5-Hydroxy-pyrrolone based building blocks as maleimide alternatives for protein bioconjugation and single-site multi-functionalization,” CHEMICAL SCIENCE, vol. 12, no. 14, pp. 5246–5252, 2021.
@article{8714036,
  abstract     = {{Recent dramatic expansion in potential uses of protein conjugates has fueled the development of a wide range of protein modification methods; however, the desirable single-site multi-functionalization of proteins has remained a particularly intransigent challenge. Herein, we present the application of 5-hydroxy-1,5-dihydro-2H-pyrrol-2-ones (5HP2Os) as advantageous alternatives to widely used maleimides for the chemo- and site-selective labeling of cysteine residues within proteins. A variety of 5HP2O building blocks have been synthesized using a one-pot photooxidation reaction starting from simple and readily accessible furans and using visible light and oxygen. These novel reagents display excellent cysteine selectivity and also yield thiol conjugates with superior stability. 5HP2O building blocks offer a unique opportunity to introduce multiple new functionalities into a protein at a single site and in a single step, thus, significantly enhancing the resultant conjugate's properties.}},
  author       = {{De Geyter, Ewout and Antonatou, Eirini and Kalaitzakis, Dimitris and Smolen, Sabina and Iyer, Abhishek and Tack, Laure and Ongenae, Emiel and Vassilikogiannakis, Georgios and Madder, Annemieke}},
  issn         = {{2041-6520}},
  journal      = {{CHEMICAL SCIENCE}},
  keywords     = {{General Chemistry,REAGENTS,CONJUGATION,STABILITY,TYROSINE,FURANS}},
  language     = {{eng}},
  number       = {{14}},
  pages        = {{5246--5252}},
  title        = {{5-Hydroxy-pyrrolone based building blocks as maleimide alternatives for protein bioconjugation and single-site multi-functionalization}},
  url          = {{http://doi.org/10.1039/d0sc05881e}},
  volume       = {{12}},
  year         = {{2021}},
}

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