Issue 47, 2017

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

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

Supplementary files

Article information

Article type
Paper
Submitted
02 Oct 2017
Accepted
15 Nov 2017
First published
15 Nov 2017

Org. Biomol. Chem., 2017,15, 10064-10072

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

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