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Chemoenzymatic approach toward the synthesis of 3-O-(α/β)-glucosylated 3-hydroxy-β-lactams

Authors
  • Decuyper, Lena
  • Franceus, Jorick
  • Dhaene, Shari
  • Debruyne, Maarten
  • Vandoorne, Kevin
  • Piens, Nicola
  • Dewitte, Griet
  • Desmet, Tom
  • D'hooghe, Matthias
Publication Date
Jan 01, 2018
Source
Ghent University Institutional Archive
Keywords
Language
English
License
Unknown
External links

Abstract

Glycosylation significantly alters the biological and physicochemical properties of small molecules. beta-Lactam alcohols comprise eligible substrates for such a transformation based on their distinct relevance in the chemical and medicinal community. In this framework, the unprecedented enzymatic glycosylation of the rigid and highly strained four-membered beta-lactam azaheterocycle was studied. For this purpose, cis-3-hydroxy-beta-lactams were efficiently prepared in three steps by means of a classical organic synthesis approach, while a biocatalytic step was implemented for the selective formation of the corresponding 3-O-alpha- and -beta-glucosides, hence overcoming the complexities typically encountered in synthetic glycochemistry and contributing to the increasing demand for sustainable processes in the framework of green chemistry. Two carbohydrate-active enzymes were selected based on their broad acceptor specificity and subsequently applied for the alpha- or beta-selective formation of beta-lactam-sugar adducts, using sucrose as a glucosyl donor.

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