Related Experiment Video
Updated: Apr 18, 2026

Biosensor-based High Throughput Biopanning and Bioinformatics Analysis Strategy for the Global Validation of Drug-protein Interactions
Published on: December 1, 2020
A configurational and conformational study of (-)-Oseltamivir using a multi-chiroptical approach
1Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka St. 44/52, 01-224 Warsaw, Poland. marcin.gorecki@icho.edu.pl.
Abstract:
To better understand structure-activity relationship (SAR) results, closely related to the structural features of (-)-Oseltamivir, four chiroptical methods, i.e. electronic circular dichroism (ECD), optical rotatory dispersion (ORD), vibrational circular dichroism (VCD), and Raman optical activity (ROA), utilizing different solvents, were employed in an effort to discover a set of the most probable conformations. Such multi-chiroptical approaches supported by quantum chemical calculations pointed out that different conformers are stable in chloroform, acetonitrile and water solutions of (-)-Oseltamivir. In this way, the most probable structures responsible for reported SAR results were established for the first time. It turned out that one of the predominant conformers in a solution is in excellent agreement with the X-ray analysis derived solid-state structure determined for (-)-Oseltamivir phosphate.
Related Concept Videos
Properties of Enantiomers and Optical Activity
¹H NMR of Conformationally Flexible Molecules: Temporal Resolution
¹H NMR of Conformationally Flexible Molecules: Variable-Temperature NMR
Molecules with Multiple Chiral Centers
Prochirality
IR and UV–Vis Spectroscopy of Carboxylic Acids
However, the stretching absorptions for the C=O bond vary depending on the structure of carboxylic acids. The C=O bond of the free carboxylic acids shows a higher stretching frequency, 1760 cm−1, while H-bonded carboxylic acids (dimers) exhibit stretching absorptions at a lower frequency,...

