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Entropy-enthalpy compensation in the methyl 5-thio-α-d-galactopyranoside-Jacalin interaction
Daniil Ahiadorme1, David Crich2
1Department of Chemistry, University of Georgia, 302 East Campus Road, Athens, GA, 30602, United States; Department of Pharmaceutical and Biomedical Sciences, University of Georgia, 250 West Green Street, Athens, GA, 30602, United States.
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.
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