Related Experiment Video
Updated: Aug 6, 2026

Chemo-enzymatic Synthesis of N-glycans for Array Development and HIV Antibody Profiling
Published on: February 5, 2018
Total Synthesis of the Proposed Structure of Threoglucin A
Natalia Cano-Sampaio1, Juan R Del Valle1
1Department of Chemistry & Biochemistry, University of Notre Dame, Notre Dame, Indiana46556, United States.
Abstract:
We report the first chemical synthesis of the proposed structure of threoglucin A, a fratricidal antibiotic produced by Streptococcus suis. An efficient tandem Mitsunobu cyclization/rearrangement strategy enabled access to all eight diastereomers of the embedded 1,3-oxazinane motif, which were incorporated into the full sequence by solid-phase peptide synthesis. Spectroscopic comparisons with the natural isolate revealed consistent discrepancies, particularly in the modified Thr8-Gln9-Gln10 region. Analysis of model systems and X-ray-validated oxazinanes established characteristic NMR spectroscopic signatures that differ from those reported for the natural products. These findings suggest that the originally proposed structure of threoglucin A warrants revision.
Related Concept Videos
Oligosaccharide Assembly
Multiple sugar molecules that may or may...
Peptidoglycan Synthesis
Production of Pharmaceuticals
Protein Folding Quality Check in the RER
Proteoglycans
Dehydration Synthesis

