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Cysteine-Selective Modification of Peptides and Proteins via Desulfurative C-C Bond Formation.
Griffiths, Rhys C; Smith, Frances R; Li, Diyuan; Wyatt, Jasmine; Rogers, David M; Long, Jed E; Cusin, Lola M L; Tighe, Patrick J; Layfield, Robert; Hirst, Jonathan D; Müller, Manuel M; Mitchell, Nicholas J.
Affiliation
  • Griffiths RC; School of Chemistry, University of Nottingham, University Park, Nottingham, NG7 2RD, UK.
  • Smith FR; School of Chemistry, University of Nottingham, University Park, Nottingham, NG7 2RD, UK.
  • Li D; School of Chemistry, University of Nottingham, University Park, Nottingham, NG7 2RD, UK.
  • Wyatt J; Department of Chemistry, King's College London, London, SE1 1DB.
  • Rogers DM; School of Chemistry, University of Nottingham, University Park, Nottingham, NG7 2RD, UK.
  • Long JE; School of Life Sciences, University of Nottingham Medical School, Nottingham, NG7 2UH, UK.
  • Cusin LML; School of Life Sciences, University of Nottingham, University Park, Nottingham, NG7 2RD, UK.
  • Tighe PJ; School of Life Sciences, University of Nottingham, University Park, Nottingham, NG7 2RD, UK.
  • Layfield R; School of Life Sciences, University of Nottingham Medical School, Nottingham, NG7 2UH, UK.
  • Hirst JD; School of Chemistry, University of Nottingham, University Park, Nottingham, NG7 2RD, UK.
  • Müller MM; Department of Chemistry, King's College London, London, SE1 1DB.
  • Mitchell NJ; School of Chemistry, University of Nottingham, University Park, Nottingham, NG7 2RD, UK.
Chemistry ; 29(16): e202202503, 2023 Mar 16.
Article in En | MEDLINE | ID: mdl-36534955
ABSTRACT
The site-selective modification of peptides and proteins facilitates the preparation of targeted therapeutic agents and tools to interrogate biochemical pathways. Among the numerous bioconjugation techniques developed to install groups of interest, those that generate C(sp3 )-C(sp3 ) bonds are significantly underrepresented despite affording proteolytically stable, biogenic linkages. Herein, a visible-light-mediated reaction is described that enables the site-selective modification of peptides and proteins via desulfurative C(sp3 )-C(sp3 ) bond formation. The reaction is rapid and high yielding in peptide systems, with comparable translation to proteins. Using this chemistry, a range of moieties is installed into model systems and an effective PTM-mimic is successfully integrated into a recombinantly expressed histone.
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Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Proteins / Cysteine Language: En Journal: Chemistry Journal subject: QUIMICA Year: 2023 Document type: Article Affiliation country: United kingdom
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Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Proteins / Cysteine Language: En Journal: Chemistry Journal subject: QUIMICA Year: 2023 Document type: Article Affiliation country: United kingdom