Реферат: L-ascorbic acid (L-Asc) is one of the most well-known and widely used active pharmaceutical ingredients (API), in particular as an apoptosis-inducing agent in cancer cells . However, still there is no complete understanding of the mechanisms of the observed effects. In our previous work, we calculated the total effective charges of L-ascorbic acid molecules in 12 binary co-crystals and in the crystal structure of pristine L-Asc (CSD). The L-Asc molecules in the studied compounds were in different conformational states, which, in addition to geometry, differed in sign of the total effective charge. This work showed that the presence of an effective charge affected the formation of crystalline structures and the system of hydrogen bonds, primarily L-ascorbic acid itself . In the crystal structure of co-crystals with pyridine-2-carboxylic (picolinic) or pyridine-3- carboxylic (nicotinic) acids, the L-Asc molecules are in only one conformational state with the negative total effective charges. Comparison of the published data on the apoptosis-inducing activity of vitamin C and L-Asc in co-crystals of L-AscPic and L-AscNic shows that the L-Asc in cocrystals possesses the highest ability to induce apoptosis. This may indicate the importance of negatively charged conformers in the apoptosis-inducing activity of L-Asc molecules. In the report the geometry and features of the electronic structure of these L-Asc conformers, their relative stability, regioselectivity descriptors (Fukui functions), and the distribution of molecular electrostatic potential will be discussed.

Библиографическая ссылка: Evtushenko D.N.
Conformers of L-Ascorbic Acid in Molecular Structure of Vitamin C and co-Crystals with Nicotinic and Picolinic Acids
The 8th Asian Symposium on Advanced Materials 03-07 Jul 2023