Entropy-enthalpy compensation in the methyl 5-thio-α-d-galactopyranoside–Jacalin interaction
Authors:
Daniil Ahiadorme a b, David Crich a b c
Affiliation:
aDepartment of Chemistry, University of Georgia, 302 East Campus Road, Athens, GA, 30602, United States
bDepartment of Pharmaceutical and Biomedical Sciences, University of Georgia, 250 West Green Street, Athens, GA, 30602, United States
cComplex Carbohydrate Research Center, University of Georgia, 315 Riverbend Road, Athens, GA, 30602, United States
Description:
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.
Publications:
- Daniil Ahiadorme; David Crich; Entropy-enthalpy compensation in the methyl 5-thio-α-d-galactopyranoside–Jacalin interaction; Carbohydrate Research, 2025
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