A series of 2-O-trifluoromethylsulfonyl-D-mannopyranosides as precursors for concomitant 18F-labeling and glycosylation by click chemistry

Simone Maschauer; Olaf Prante

doi:10.1016/j.carres.2009.02.001

A series of 2-O-trifluoromethylsulfonyl-D-mannopyranosides as precursors for concomitant 18F-labeling and glycosylation by click chemistry

Carbohydr Res. 2009 Apr 21;344(6):753-61. doi: 10.1016/j.carres.2009.02.001. Epub 2009 Feb 8.

Authors

Simone Maschauer¹, Olaf Prante

Affiliation

¹ Laboratory of Molecular Imaging, Clinic of Nuclear Medicine, Friedrich-Alexander University Erlangen-Nürnberg, Erlangen, Germany.

PMID: 19303067
DOI: 10.1016/j.carres.2009.02.001

Abstract

A series of 'clickable' mannopyranosides bearing a triflate leaving group at C-2 position were synthesized and tested for their potential as (18)F-labeling precursors. 3,4,6-Tri-O-acetyl-2-O-trifluoromethanesulfonyl-beta-D-mannopyranosyl azide (2beta) was the most convenient precursor for a site-specific and reliable click chemistry-based three-step, two-pot concomitant (18)F-labeling and glycosylation of an alkyne-functionalized amino acid derivative.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Fluorine Radioisotopes / chemistry*
Glycosylation
Magnetic Resonance Spectroscopy
Mannose / chemical synthesis*
Mannose / chemistry*
Molecular Structure
Positron-Emission Tomography

Substances

Fluorine Radioisotopes
Mannose