Entropy-enthalpy compensation in the methyl 5-thio-α-d-galactopyranoside-Jacalin interaction.

ABSTRACT: Methyl 5-thio-α-d-galactopyranoside was synthesized and found to have a more favorable enthalpy of binding to Jacalin than methyl α-d-galactopyranoside, which is attributed to the greater magnitude of sulfur-π over oxygen-π interactions. This increase in enthalpy, however, was offset by a less favorable entropy of binding, arising from the need to constrain the more flexible thiosugar, thereby highlighting the complexities inherent in the design of effective sugar mimetics.

SUBMITTER: Ahiadorme D 

PROVIDER: S-EPMC11620909 | biostudies-literature | 2025 Jan

REPOSITORIES: biostudies-literature