Top-down chemoenzymatic approach to a high-mannose-type glycan library: synthesis of a common precursor and its enzymatic trimming

Angew Chem Int Ed Engl. 2013 Jul 15;52(29):7426-31. doi: 10.1002/anie.201301613. Epub 2013 Jun 5.

Abstract

From the stacks: A novel method for construction of a high-mannose-type glycan library by systematic enzymatic trimming of a single synthetic Man9-based precursor was developed. Efficient chemical synthesis of the tetradecasaccharide common precursor and orthogonal enzymatic trimming to obtain all M(8-9) and G(1)M(8-9) derivatives was demonstrated. G = glucose, M = mannose.

Keywords: carbohydrates; enzymes; glycopeptides; protein folding; synthesis design.

MeSH terms

  • Boron Compounds / chemistry
  • Carbohydrate Sequence
  • Glycoproteins / chemistry
  • Glycoproteins / metabolism
  • Glycoside Hydrolases / metabolism
  • Mannose / chemistry*
  • Molecular Sequence Data
  • Polysaccharides / chemical synthesis
  • Polysaccharides / chemistry*
  • Protein Folding

Substances

  • 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
  • Boron Compounds
  • Glycoproteins
  • Polysaccharides
  • Glycoside Hydrolases
  • Mannose