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Synthesis of N -glycosyl amides: conformational analysis and evaluation as inhibitors of β-galactosidase from E. coli .

Miqueas G TraverssiVerónica E ManzanoOscar VarelaJuan Pablo Colomer
Published in: RSC advances (2024)
The synthesis of N -glycosyl amides typically involves the use of glycosyl amines as direct precursors, resulting in low yields due to hydrolysis and the loss of stereocontrol through anomerization processes. In this study, a sequential synthesis of N -glycosyl amides is proposed, employing glycosyl amines as intermediates obtained from glycosyl azides. Derivatives with gluco , galacto , or xylo configurations were synthesized. Hexose derivatives were obtained under stereocontrol to give only the β anomer, while the xylo derivatives provided a mixture of α and β anomers. Conformational analysis revealed that all β anomers adopted the 4 C 1 conformation, while α anomers were found in the 1 C 4 chair as the major conformer. After de- O -acetylation, the derivatives containing a galactose unit were evaluated as inhibitors of β-galactosidase from E. coli and were found to be moderate inhibitors.
Keyphrases
  • molecular dynamics simulations
  • escherichia coli
  • structure activity relationship
  • single molecule
  • single cell