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Facile Discrimination of Aldose Enantiomers by Reversed-Phase HPLC
Chemical and Pharmaceutical Bulletin · 2007 · Vol. 55(6) · pp. 899–901
Takashi Tanaka✉(Nagasaki University)Tatsuya Nakashima(Nagasaki University)Toshihisa Ueda(Saga University)Kenji Tomii(Nagasaki University)Isao Kouno(Nagasaki University)
Abstract
One-pot reactions of aldoses with L-cysteine methyl ester and o-tolyl isothiocyanate yielded methyl 2-(polyhydroxyalkyl)-3-(o-tolylthiocarbamoyl)-thiazolidine-4(R)-carboxylates. Direct HPLC analysis of the reaction mixture and UV detection at 250 nm discriminated D- and L-enantiomers of aldoses. The reaction was applied to the determination of absolute configuration the sugar residues of an aroma precursor.
Natural product bioactivities and synthesisCarbohydrate Chemistry and SynthesisPharmacological Effects of Natural CompoundsChemistryEnantiomerAldoseThiazolidineHigh-performance liquid chromatographyChromatographyIsothiocyanateAromaAbsolute configurationKetose
MeSH terms
Chromatography, High Pressure LiquidMonosaccharidesSpectrophotometry, UltravioletStereoisomerismSpectrometry, Mass, Fast Atom Bombardment
Funding
- Japan Society for the Promotion of Science
Citations
833
FWCI
3.62
field-weighted impact
References
8
Percentile
94%
vs. same field & year
Citations per year
References
Gas-liquid chromatographic separation of aldose enantiomers as trimethylsilyl ethers of methyl 2-(polyhydroxyalkyl)-thiazolidine-4(R)-carboxylates.
Chemical and Pharmaceutical Bulletin · 1987 · 543 citations
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