Chemical synthesis of natural and azido-modified UDP-rhamnose and -arabinofuranose for glycan array-based characterization of plant glycosyltransferases

Irene Pasini; Colin Ruprecht; Uwe Osswald; Andreas Bittmann; Lina Maltrovsky; Cecilia Romanò; Mads H Clausen; Fabian Pfrengle

doi:10.1039/d4cc02095b

Chemical synthesis of natural and azido-modified UDP-rhamnose and -arabinofuranose for glycan array-based characterization of plant glycosyltransferases

Chem Commun (Camb). 2024 Aug 27;60(70):9368-9371. doi: 10.1039/d4cc02095b.

Authors

Irene Pasini¹, Colin Ruprecht¹, Uwe Osswald¹, Andreas Bittmann¹, Lina Maltrovsky¹, Cecilia Romanò², Mads H Clausen², Fabian Pfrengle¹

Affiliations

¹ Institute of Organic Chemistry, Department of Chemistry, BOKU University, Muthgasse 18, 1190, Vienna, Austria. Fabian.pfrengle@boku.ac.at.
² Center for Nanomedicine and Theranostics, Department of Chemistry, Technical University of Denmark, Kemitorvet, Building 207, 2800 Kongens Lyngby, Denmark.

PMID: 39135501
DOI: 10.1039/d4cc02095b

Abstract

Chemical syntheses of UDP-rhamnose and UDP-arabinofuranose and respective azido-modified analogues are reported. The prepared substrates are useful for the glycan array-based analysis of glycosyltransferases, as exemplified with the plant cell wall-biosynthetic enzymes PvXAT3, AtRRT4 and PtRRT5.

MeSH terms

Arabinose / analogs & derivatives
Arabinose / chemistry
Azides / chemistry
Glycosyltransferases* / chemistry
Glycosyltransferases* / metabolism
Plants / chemistry
Polysaccharides* / chemical synthesis
Polysaccharides* / chemistry
Polysaccharides* / metabolism
Uridine Diphosphate Sugars* / chemistry
Uridine Diphosphate Sugars* / metabolism

Substances

Glycosyltransferases
Polysaccharides
Uridine Diphosphate Sugars
UDP-rhamnose
Azides
Arabinose
arabinofuranose