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Fluorescent mannosides serve as acceptor substrates for glycosyltransferase and sugar-1-phosphate transferase activities in Euglena gracilis membranes.


ABSTRACT: Synthetic hexynyl ?-D-mannopyranoside and its ?-1,6-linked disaccharide counterpart were fluorescently labelled through CuAAC click chemistry with 3-azido-7-hydroxycoumarin. The resulting triazolyl-coumarin adducts, which were amenable to analysis by TLC, HPLC and mass spectrometry, proved to be acceptor substrates for ?-1,6-ManT activities in mycobacterial membranes, as well as ?- and ?-GalT activities in trypanosomal membranes, benchmarking the potential of the fluorescent acceptor approach against earlier radiochemical assays. Following on to explore the glycobiology of the benign protozoan alga Euglena gracilis, ?-1,3- and ?-1,2-ManT activities were detected in membrane preparations, along with GlcT, Glc-P-T and GlcNAc-P-T activities. These studies serve to demonstrate the potential of readily accessible fluorescent glycans as substrates for exploring carbohydrate active enzymes.

SUBMITTER: Ivanova IM 

PROVIDER: S-EPMC5240791 | biostudies-literature | 2017 Jan

REPOSITORIES: biostudies-literature

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Fluorescent mannosides serve as acceptor substrates for glycosyltransferase and sugar-1-phosphate transferase activities in Euglena gracilis membranes.

Ivanova Irina M IM   Nepogodiev Sergey A SA   Saalbach Gerhard G   O'Neill Ellis C EC   Urbaniak Michael D MD   Ferguson Michael A J MA   Gurcha Sudagar S SS   Besra Gurdyal S GS   Field Robert A RA  

Carbohydrate research 20161130


Synthetic hexynyl α-D-mannopyranoside and its α-1,6-linked disaccharide counterpart were fluorescently labelled through CuAAC click chemistry with 3-azido-7-hydroxycoumarin. The resulting triazolyl-coumarin adducts, which were amenable to analysis by TLC, HPLC and mass spectrometry, proved to be acceptor substrates for α-1,6-ManT activities in mycobacterial membranes, as well as α- and β-GalT activities in trypanosomal membranes, benchmarking the potential of the fluorescent acceptor approach ag  ...[more]

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