Stereoselective Synthesis Data for Antiphage Thiolactone Glycomimetics

Synthesis data details the stereocontrolled creation of bicyclic thiolactone compounds from methyl α-mannopyranoside and methyl α-galactopyranoside precursors. The dataset, authored by Karol Postrożny and uploaded in April 2026, includes results from a multi-step synthetic route and subsequent biological activity testing. It demonstrates how stereochemical control dictates selective antiphage activity against bacteriophage T4.

Use Cases

• Analyze the relationship between carbohydrate precursor (methyl α-mannopyranoside vs. methyl α-galactopyranoside) and the diastereoselectivity of the cyclization reaction.
• Identify structural features from NMR and X-ray analysis data that correlate with the >2-log reduction in PFU for bacteriophage T4 observed in compound 29.
• Model the substituent-dependent stereochemical outcomes described for d-galactoside analogues to predict synthetic pathways.
• Use synthesis step data (iodination, protection, fragmentation, domino reaction) to optimize reaction conditions for similar compounds.

Strengths

• Structural assignments were confirmed by two-dimensional NMR spectroscopy and X-ray analyses, providing high-confidence data.
• The study demonstrates complete diastereoselectivity for d-mannoside derivatives, offering a clear synthetic benchmark.
• Biological activity data includes a specific >2-log reduction in plaque-forming units (PFU) for a key compound.

Limitations

• The dataset is very small at 604.7 KB, indicating limited scope, likely covering only the specific compounds synthesized in this study.
• The exact number of synthesized compounds, rows of data, or specific measured columns are not provided.
• Biological activity is tested against a single bacteriophage (T4), limiting generalizability to other viruses.

Provenance

Source

Figshare, authored by Karol Postrożny.

Collection Method

Experimental data from laboratory synthesis, NMR/X-ray characterization, and phage inactivation assays.

Freshness

Last updated in April 2026, indicating recent data.