Synthesis of fluorosugar reagents for the construction of well-defined fluoroglycoproteins

Míriam Salvadó; Beatrice Amgarten; Sergio Castillón; Gonçalo J L Bernardes; Omar Boutureira

doi:10.1021/acs.orglett.5b01259

Synthesis of fluorosugar reagents for the construction of well-defined fluoroglycoproteins

Org Lett. 2015 Jun 5;17(11):2836-9. doi: 10.1021/acs.orglett.5b01259. Epub 2015 May 22.

Authors

Míriam Salvadó¹, Beatrice Amgarten², Sergio Castillón¹, Gonçalo J L Bernardes^{2

3}, Omar Boutureira¹

Affiliations

¹ †Departament de Química Analítica i Química Orgànica, Universitat Rovira i Virgili, C/Marcel·lí Domingo s/n, 43007 Tarragona, Spain.
² ‡Department of Chemistry, University of Cambridge, Lensfield Road, CB2 1EW Cambridge, U.K.
³ §Instituto de Medicina Molecular, Faculdade de Medicina da Universidade de Lisboa, Av. Prof. Egas Moniz, 1649-028 Lisboa, Portugal.

PMID: 25997669
DOI: 10.1021/acs.orglett.5b01259

Abstract

2-Deoxy-2-fluoroglycosyl iodides are privileged glycosyl donors for the stereoselective preparation of 1-Nu-β-fluorosugars, which are useful reagents for chemical site-selective protein glycosylation. Ready access to such β-fluorosugars enables the mild and efficient construction of well-defined fluoroglycoproteins.

Publication types

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

MeSH terms

Glycoproteins / chemical synthesis*
Glycoproteins / chemistry
Glycosides / chemical synthesis*
Glycosides / chemistry
Glycosylation
Hydrocarbons, Fluorinated / chemistry*
Indicators and Reagents / chemistry*
Molecular Structure

Substances

Glycoproteins
Glycosides
Hydrocarbons, Fluorinated
Indicators and Reagents