Direct enantiomeric TLC resolution of dl‐penicillamine using (R)‐mandelic acid and l‐tartaric acid as chiral impregnating reagents and as chiral mobile phase additive

Abstract

DL-Penicillamine has been resolved into its enantiomers by normal-phase TLC using L-tartaric acid as chiral impregnating reagent as well as chiral mobile phase additive, while (R)-mandelic acid has been found to be successful as a chiral impregnating reagent. The solvent system acetonitrile-methanol-water (5:1:1, v/v) was found to be successful when L-tartaric acid was used as impregnating agent while the solvent combination acetonitrile-methanol-(0.5% l-tartaric acid in water, pH 5)-glacial acetic acid (7:1:1.1:0.7, v/v) was successful as mobile phase as it contained L-tartaric acid as the chiral additive. (R)-mandelic acid was successful as chiral impregnating reagent with ethyl acetate-methanol-water (3:1:1, v/v), as the mobile phase. The effects of concentration of chiral selectors, temperature and pH were examined on enantiomeric resolution. The spots were detected with iodine vapors and the detection limits were found to be 0.12 microg for each enantiomer of penicillamine with L-tartaric acid, under both the conditions, and 0.11 microg with (R)-mandelic acid.

Turn-on fluorescence probe for selective and sensitive detection of d-penicillamine by CdS quantum dots in aqueous media: Application to pharmaceutical formulation

“…The sensitivity and limit of detection value (LOD) of our proposed method is compared with other various published methods. The comparison chart is shown in Table 1 [16,17,[47][48][49][50][51][52]. The proposed method shows very good sensitivity with lowest detection limit for obtained value as compared to the other methods.…”

Metabolic engineering of the L-phenylalanine pathway in Escherichia coli for the production of S- or R-mandelic acid

“…Mandelic acid (MA), an important fine chemical, has been widely used in the synthesis of cephalosporin antibiotics [1], the preparation of various other pharmaceuticals [2-4], as well as the resolution of racemic alcohols and amines [5,6]. Its stereoisomers generally are prepared using a chemical approach [7-9].…”

Enantioresolution of Amino Acids: A Decade’s Perspective, Prospects and Challenges

“…This effect decreases the chiral recognition. Bhushan and Agarwal [44] reported a method for direct TLC resolution and isolation of enantiomers of dl-PenA using l-tartaric acid and (R)-mandelic HPLC β 2 -Amino acids Chiral stationary phases containing quinine-or quinidine-based zwitterionic selectors UV [191] HPLC dl-Penicillamine and dl-cysteine α-Acid glycoprotein and β-cyclodextrin columns UV-231 nm [77] HPLC γ-Amino acids CSP based on (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid UV-210 nm [107] HPLC N-Fluorenylmethoxycarbonyl α-amino acids Polysaccharide-derived chiral stationary phases DAD [109] HPLC β 3 -Homo-amino acid (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid-based CSP UV-210 nm [104] HPLC Dansyl amino acids Cyclic hexapeptide as chiral selector [192] HPLC β-Amino acids (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid-based CSP [105] HPLC N-(3,5-Dinitrobenzoyl)-α-amino acids (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid-based CSP [ Polarimeter [193] acid as chiral impregnating reagent as well as CMPA. The detection limits were found to be 0.12 μg for each enantiomer of PenA with l-tartaric acid, under both the conditions, and 0.11 μg with (R)-mandelic acid.…”