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18F-Trifluoromethanesulfinate Enables Direct C-H 18F-Trifluoromethylation of Native Aromatic Residues in Peptides.
Kee, Choon Wee; Tack, Osman; Guibbal, Florian; Wilson, Thomas C; Isenegger, Patrick G; Imiolek, Mateusz; Verhoog, Stefan; Tilby, Michael; Boscutti, Giulia; Ashworth, Sharon; Chupin, Juliette; Kashani, Roxana; Poh, Adeline W J; Sosabowski, Jane K; Macholl, Sven; Plisson, Christophe; Cornelissen, Bart; Willis, Michael C; Passchier, Jan; Davis, Benjamin G; Gouverneur, Véronique.
Afiliação
  • Kee CW; Chemistry Research Laboratory , University of Oxford , 12 Mansfield Road , Oxford OX1 3TA , U.K.
  • Tack O; Chemistry Research Laboratory , University of Oxford , 12 Mansfield Road , Oxford OX1 3TA , U.K.
  • Guibbal F; Chemistry Research Laboratory , University of Oxford , 12 Mansfield Road , Oxford OX1 3TA , U.K.
  • Wilson TC; Radiobiology Research Institute, Department of Oncology , University of Oxford , Headington, Oxford OX3 7LJ , U.K.
  • Isenegger PG; Chemistry Research Laboratory , University of Oxford , 12 Mansfield Road , Oxford OX1 3TA , U.K.
  • Imiolek M; Chemistry Research Laboratory , University of Oxford , 12 Mansfield Road , Oxford OX1 3TA , U.K.
  • Verhoog S; Chemistry Research Laboratory , University of Oxford , 12 Mansfield Road , Oxford OX1 3TA , U.K.
  • Tilby M; Chemistry Research Laboratory , University of Oxford , 12 Mansfield Road , Oxford OX1 3TA , U.K.
  • Boscutti G; Chemistry Research Laboratory , University of Oxford , 12 Mansfield Road , Oxford OX1 3TA , U.K.
  • Ashworth S; Invicro Ltd , Du Cane Road , London W12 0NN , U.K.
  • Chupin J; Invicro Ltd , Du Cane Road , London W12 0NN , U.K.
  • Kashani R; Invicro Ltd , Du Cane Road , London W12 0NN , U.K.
  • Poh AWJ; Centre for Molecular Oncology, Barts Cancer Institute , Queen Mary University of London , London EC1M 6BQ , U.K.
  • Sosabowski JK; Centre for Molecular Oncology, Barts Cancer Institute , Queen Mary University of London , London EC1M 6BQ , U.K.
  • Macholl S; Chemistry Research Laboratory , University of Oxford , 12 Mansfield Road , Oxford OX1 3TA , U.K.
  • Plisson C; Centre for Molecular Oncology, Barts Cancer Institute , Queen Mary University of London , London EC1M 6BQ , U.K.
  • Cornelissen B; Invicro Ltd , Du Cane Road , London W12 0NN , U.K.
  • Willis MC; Centre for Molecular Oncology, Barts Cancer Institute , Queen Mary University of London , London EC1M 6BQ , U.K.
  • Passchier J; Invicro Ltd , Du Cane Road , London W12 0NN , U.K.
  • Davis BG; Radiobiology Research Institute, Department of Oncology , University of Oxford , Headington, Oxford OX3 7LJ , U.K.
  • Gouverneur V; Chemistry Research Laboratory , University of Oxford , 12 Mansfield Road , Oxford OX1 3TA , U.K.
J Am Chem Soc ; 142(3): 1180-1185, 2020 01 22.
Article em En | MEDLINE | ID: mdl-31913613
ABSTRACT
18F labeling strategies for unmodified peptides with [18F]fluoride require 18F-labeled prosthetics for bioconjugation more often with cysteine thiols or lysine amines. Here we explore selective radical chemistry to target aromatic residues applying C-H 18F-trifluoromethylation. We report a one-step route to [18F]CF3SO2NH4 from [18F]fluoride and its application to direct [18F]CF3 incorporation at tryptophan or tyrosine residues using unmodified peptides as complex as recombinant human insulin. The fully automated radiosynthesis of octreotide[Trp(2-CF218F)] enables in vivo positron emission tomography imaging.
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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Peptídeos / Compostos de Enxofre / Radioisótopos de Flúor / Clorofluorcarbonetos de Metano Idioma: En Revista: J Am Chem Soc Ano de publicação: 2020 Tipo de documento: Article País de afiliação: Reino Unido
Texto completo
Imprimir
XML
PubMed Links
Buscar no Google

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Peptídeos / Compostos de Enxofre / Radioisótopos de Flúor / Clorofluorcarbonetos de Metano Idioma: En Revista: J Am Chem Soc Ano de publicação: 2020 Tipo de documento: Article País de afiliação: Reino Unido