The intramolecular stabilizing effects of <i>O</i>-benzoyl substituents as a driving force of the acid-promoted pyranoside-<i>into</i>-furanoside rearrangement.

ABSTRACT: Furanoside derivatives are broadly present in the antigenic structures of pathogenic microorganisms and play a key role in their recognition by the host immune system. Despite the high demand for vaccine and diagnostic development, their chemical synthesis remains challenging. During the development of a new methodology for the synthesis of galactofuranoside building blocks, we encountered an unexpected predominance of the furanoside form in the equilibrium mixture of benzoylated β-galactosides. Since the furanoside form is typically less stable and is usually present only in minor amounts, we turned to computational studies to elucidate the driving force of this pyranoside-into-furanoside isomerisation. The DFT B3LYP-D3 approach was employed for this task with additional validation

SUBMITTER: Gerbst AG 

PROVIDER: S-EPMC12599399 | biostudies-literature | 2025

REPOSITORIES: biostudies-literature