Ritalin, [(+)-threo]methylphenidate hydrochloride, is a chiral drug substance with two chiral centers. The drug substance may contain three pairs of enantiomers, [(+)-threo], [(-)-threo], [(+)-erythro] and [(-)-erythro] isomers, and its degradation products, threoritalinic acid racemate. Determination of the optical purity of ritalin drug substance and the amount of its by-product isomers is a critical step in the single-isomer drug development. In order to efficiently recognize the three pairs of enantiomers by one method, capillary electrophoresis (CE) was employed for the separation. The three pairs of enantiomers in CE showed different enantioselectivities with eight different types of CDs. Only 2,6-di-o-methyl-beta-cyclodextrin (DM-beta-CD) and carboxymethyl-beta-cyclodextrin (CM-beta-CD) showed enantioselectivity to all these pairs of enantiomers. With respect to separation resolution and efficiency, DM-beta-CD was chosen as the chiral selector. For optimization of the separation conditions, the concentration of DM-beta-CD, pH of the buffer solution, and temperature of the capillary were further studied.
Benzofuran‐2‐yl methyl ketone (BMK) is a prochiral ketone that is reduced to benzofuran‐2‐yl ethanol (BMA) when exposed to tissues of certain plants. The process of using biological tissue to convert one compound to another, typically with high enantiomeric excess, is called a biotransformation reaction. Because different plants catalyze this conversion, the primary goals of this research were to identify plants that are successful in conversion, determine an approximate time necessary for each plant to perform the conversion, and then analyze the product of each plant to determine the enantiomeric excess. Optical purity of BMA was determined using polarimetry. The BMA produced by carrots had a [α] = −16.6 which agrees with the literature value for the S‐isomer of BMA. However, the BMA produced by potatoes had a [α] = −.74 which may indicate a mixture that is nearly racemic. To explore the reaction further, antimicrobial studies were carried out adding either BMK or BMA to YPD agar plates growing with Baker's yeast. In these preliminary studies, S‐BMA, produced by carrots, consistently demonstrated a greater growth inhibition of the Baker's yeast than BMK. The growth inhibition of the yeast by BMA was dose dependent. The antimicrobial studies were also expanded to BL21 E. coli grown on LB agar, showing similar results to those of yeast. The antimicrobial activity of S‐BMA against yeast and bacteria was also compared to that of the racemic mixture produced by potato, which showed no significant differences between the two. The antifungal activity of BMA against yeast was then compared to the common over‐the‐counter antifungal compounds miconazole, clotrimazole, terbinafine and tolnaftate. The latter two had no effect on growth, but miconazole and clotrimazole inhibited yeast growth substantially. The antibacterial activity of BMA against E. coli was compared to ampicillin. In these preliminary antimicrobial studies, BMA has shown comparable activity to common compounds.This abstract is from the Experimental Biology 2018 Meeting. There is no full text article associated with this abstract published in The FASEB Journal.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.
hi@scite.ai
10624 S. Eastern Ave., Ste. A-614
Henderson, NV 89052, USA
Copyright © 2024 scite LLC. All rights reserved.
Made with 💙 for researchers
Part of the Research Solutions Family.