Format

Send to

Choose Destination
Angew Chem Int Ed Engl. 2018 Sep 24;57(39):12733-12736. doi: 10.1002/anie.201806966. Epub 2018 Sep 5.

Site-Selective, Late-Stage C-H 18 F-Fluorination on Unprotected Peptides for Positron Emission Tomography Imaging.

Author information

1
Department of Chemistry, Simon Fraser University Burnaby, British Columbia, V5A 1S6, Canada.
2
Life Science Division, TRIUMF, Vancouver, BC, V6T 2A3, Canada.
3
Department of Molecular Oncology, BC Cancer Agency, Vancouver, British Columbia, V5Z 1L3, Canada.
4
Medicinal Chemistry, Roche Pharma Research and Early Development (pRED), Roche Innovation Center Basel, F. Hoffmann-La Roche Ltd, Grenzacherstrasse 124, CH-4070, Basel, Switzerland.

Abstract

Peptides are often ideal ligands for diagnostic molecular imaging due to their ease of synthesis and tuneable targeting properties. However, labelling unmodified peptides with 18 F for positron emission tomography (PET) imaging presents a number of challenges. Here we show the combination of photoactivated sodium decatungstate and [18 F]-N-fluorobenzenesulfonimide effects site-selective 18 F-fluorination at the branched position in leucine residues in unprotected and unaltered peptides. This streamlined process provides a means to directly convert native peptides into PET imaging agents under mild aqueous conditions, enabling rapid discovery and development of peptide-based molecular imaging tools.

KEYWORDS:

18F-fluorination; PET imaging; peptides; photocatalysis; radiolabeling

PMID:
30086209
DOI:
10.1002/anie.201806966
[Indexed for MEDLINE]

Supplemental Content

Full text links

Icon for Wiley
Loading ...
Support Center