The Generally Useful Estimate of Solvent Systems (GUESS) method enables the rapid purification of methylpyridoxine regioisomers by countercurrent chromatography

• Published in: Journal of Chromatography A Vol. 1426; pp. 248 - 251
• Main Authors: Liu, Yang, Friesen, J. Brent, Klein, Larry L., McAlpine, James B., Lankin, David C., Pauli, Guido F., Chen, Shao-Nong
• Format: Journal Article
• Language: English
• Published: Netherlands Elsevier B.V 24.12.2015
• Subjects: Chloroform - chemistry; Countercurrent Distribution; Countercurrent separation; Generally useful estimate of solvent systems; Ginkgo biloba; Ginkgotoxin isomers; Methanol - chemistry; Pyridoxine - analogs & derivatives; Pyridoxine - isolation & purification; Quantitative 1H NMR; Solvents - chemistry; Stereoisomerism; Thin layer chromatography; Water - chemistry; Ginkgo biloba; Thin layer chromatography; Quantitative 1H NMR; Ginkgotoxin isomers; Countercurrent separation; Generally useful estimate of solvent systems; Quantitative H NMR
• ISSN: 0021-9673; 1873-3778
• DOI: 10.1016/j.chroma.2015.11.046

•The synthetic scheme for ginkgotoxin and two positional isomers is described.•TLC-based Generally Useful Estimate of Solvent Systems method is reintroduced.•Countercurrent chromatography is used to purify three ginkgotoxin positional isomers.•Purity and structure characterization of all samples was done by quantitative 1H NMR. The TLC-based Generally Useful Estimate of Solvent Systems (GUESS) method was employed for countercurrent chromatography solvent system selection, in order to separate the three synthetic isomers: 3-O-methylpyridoxine, 4′-O-methylpyridoxine (ginkgotoxin), and 5′-O-methylpyridoxine. The Rf values of the three isomers indicated that ChMWat+2 (chloroform-methanol-water 10:5:5, v/v/v) was appropriate for the countercurrent separation. The isomer separation was highly selective and demonstrated that the TLC-based GUESS method can accelerate solvent system selection for countercurrent separation. Accordingly, the study re-emphasizes the practicality of TLC as a tool to facilitate the rapid development of new countercurrent and centrifugal partition chromatography methods for this solvent system. Purity and structure characterization of all samples was performed by quantitative 1H NMR.