Jump to main content
Jump to site search

Issue 47, 2017
Previous Article Next Article

Complete tetraglycosylation of a calix[4]arene by a chemo-enzymatic approach

Author affiliations

Abstract

Polyglycosylated calixarenes are efficient and selective multivalent ligands for lectins. However, the chemical decoration of these macrocyclic scaffolds with saccharides of increasing complexity is hampered by the highly complex chemistry of carbohydrates. An alternative to the conventional approach is the enzymatic diversification of simple glycocluster-presented glycans. In this work, we present a highly efficient chemo-enzymatic approach to tetra-N-acetyl-lactosaminylcalix[4]arene via glycan extension catalyzed by a human β-1,4-galactosyltransferase. This demonstrates that calixarenes can be exhaustively processed by enzymatic glycosyl transfer despite the heavy steric crowding, paving the way to the design and achievement of multivalent ligands based on these macrocyclic scaffolds having complex branched glycans.

Graphical abstract: Complete tetraglycosylation of a calix[4]arene by a chemo-enzymatic approach

Back to tab navigation

Supplementary files

Publication details

The article was received on 02 Oct 2017, accepted on 15 Nov 2017 and first published on 15 Nov 2017


Article type: Paper
DOI: 10.1039/C7OB02448G
Citation: Org. Biomol. Chem., 2017,15, 10064-10072
  •   Request permissions

    Complete tetraglycosylation of a calix[4]arene by a chemo-enzymatic approach

    S. Bernardi, D. Yi, N. He, A. Casnati, W. Fessner and F. Sansone, Org. Biomol. Chem., 2017, 15, 10064
    DOI: 10.1039/C7OB02448G

Search articles by author

Spotlight

Advertisements