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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| http://dx.doi.org/10.1016/j.carres.2024.109305 | DOI Listing |
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Entropy-enthalpy compensation in the methyl 5-thio-α-d-galactopyranoside-Jacalin interaction.
Carbohydr Res
January 2025
Department 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; Complex Carbohydrate Research Center, University of Georgia, 315 Riverbend Road, Athens, GA, 30602, United States. Electronic address:
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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J Med Chem
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Laboratory of Chemical Physics, National Institute of Diabetes and Digestive and Kidney Diseases, National Institutes of Health, DHHS, Bethesda, Maryland 20892-0520, United States.
SARS-CoV-2 propagation under nirmatrelvir and ensitrelvir pressure selects for main protease (MPro) drug-resistant mutations E166V (DRM2), L50F/E166V (DRM3), E166A/L167F (DRM4), and L50F/E166A/L167F (DRM5). DRM2-DRM5 undergoes N-terminal autoprocessing to produce mature MPro with dimer dissociation constants () 2-3 times larger than that of the wildtype. Co-selection of L50F restores catalytic activity of DRM2 and DRM4 from ∼10 to 30%, relative to that of the wild-type enzyme, without altering .
View Article and Find Full Text PDFPhase separation of triton X-100 and bovine serum albumin mixture: Impacts of nature and composition of polyols on associated physicochemical parameters.
Int J Biol Macromol
November 2024
Department of Chemistry, Jahangirnagar University, Savar, Dhaka 1342, Bangladesh.
Article Synopsis
- Bovine serum albumin (BSA) is a useful substance in tissue engineering and pharmaceutical research, derived from cattle blood.
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Reaction Kinetics of the Benzylation of Adenine in DMSO: Regio-Selectivity Guided by Entropy.
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Department of Chemistry, University of Pretoria, Pretoria, 0002, Republic of South Africa.
The factors governing the regio-selectivity of the alkylation of adenine have been of interest for many years due to the biological importance of adenine derivatives, however, no reaction kinetic studies have been conducted. Herein, we report the rate constants and activation parameters of the benzylation of adenine under basic conditions in DMSO in the absence and presence of 15-crown-5 ether using real-time H NMR spectroscopy. The reaction is second-order for the formation of the N9- and N3-benzyladenine products, with a regio-selectivity factor 2.
View Article and Find Full Text PDFSolvent quality and nonbiological oligomer folding: revisiting conventional paradigms.
Soft Matter
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Dipartimento di Scienze Molecolari e Nanosistemi, Università Ca' Foscari Venezia, Via Torino 155, 30172 Venezia, Italy.
We report on extensive molecular dynamics atomistic simulations of a -substituted poly-phenylacetylene (pPA) foldamer dispersed in three solvents, water HO, cyclohexane cCH, and -hexane CH, and for three oligomer lengths 12mer, 16mer and 20mer. At room temperature, we find a tendency of the pPA foldamer to collapse into a helical structure in all three solvents but with rather different stability character, stable in water, marginally stable in -hexane, unstable in cyclohexane. In the case of water, the initial and final number of hydrogen bonds of the foldamer with water molecules is found to be unchanged, with no formation of intrachain hydrogen bonding, thus indicating that hydrogen bonding plays no role in the folding process.
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