Related Experiment Video
Updated: Sep 2, 2025

Hierarchical and Programmable One-Pot Oligosaccharide Synthesis
Published on: September 6, 2019
Erwinia tasmaniensis levansucrase shows enantiomer selection for (S)-1,2,4-butanetriol
Ivan Polsinelli1, Marco Salomone-Stagni1, Stefano Benini1
1Bioorganic Chemistry and Bio-Crystallography Laboratory (B2Cl), Faculty of Science and Technology, Free University of Bolzano, Piazza Universita 5, 39100 Bolzano, Italy.
Abstract:
Levansucrases are biotechnologically interesting fructosyltransferases due to their potential use in the enzymatic or chemo-enzymatic synthesis of glycosides of non-natural substrates relevant to pharmaceutical applications. The structure of Erwinia tasmaniensis levansucrase in complex with (S)-1,2,4-butanetriol and its biochemical characterization suggests the possible application of short aliphatic moieties containing polyols with defined stereocentres in fructosylation biotechnology. The structural information revealed that (S)-1,2,4-butanetriol mimics the natural substrate. The preference of the protein towards a specific 1,2,4-butanetriol enantiomer was assessed using microscale thermophoresis binding assays. Furthermore, the results obtained and the structural comparison of levansucrases and inulosucrases suggest that the fructose binding modes could differ in fructosyltransferases from Gram-positive and Gram-negative bacteria.
Related Concept Videos
Prochirality
Sharpless Epoxidation
Properties of Enantiomers and Optical Activity
Naming Enantiomers
E1 Reaction: Stereochemistry and Regiochemistry
SN2 Reaction: Stereochemistry
If the substrate is an achiral molecule at the α-carbon, the inversion of configuration is not...

