Enantiomer separation and indirect chromatographic absolute configuration prediction of chiral pirinixic acid derivatives: Limitations of polysaccharide-type chiral stationary phases in comparison to chiral anion-exchangers

Lämmerhofer, Michael; Pell, Reinhard; Mahut, Marek; Richter, Martin; Schiesel, Simone; Zettl, Heiko; Dittrich, Michaela; Schubert‐Zsilavecz, Manfred; Lindner, Wolfgang

doi:10.1016/j.chroma.2009.10.048

Cited by 19 publications

(24 citation statements)

References 46 publications

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“…The elution order determination for the enantiomers of 1′‐Oxo‐BF is not available in the literature. For this purpose, a combination of chromatographic and CD methods was used to determine the absolute configuration 24 of 1′‐Oxo‐BF enantiomers by comparison of CD spectra with BF enantiomers. For 1′‐Oxo‐BF (Fig.…”

Section: Resultsmentioning

confidence: 99%

Stereoselective liquid chromatographic determination of 1′‐oxobufuralol and 1′‐hydroxybufuralol in rat liver microsomal fraction using hollow‐fiber liquid‐phase microextraction for sample preparation

Barth

Simões

Pupo

et al. 2011

J of Separation Science

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A three-phase hollow-fiber liquid-phase microextraction (HF-LPME) method for the stereoselective determination of bufuralol metabolites 1'-oxobufuralol (1'-Oxo-BF) and 1'-hydroxybufuralol (1'-OH-BF) in microsomal preparations is described for the first time. The HPLC analysis was carried out using a Chiralcel OD-H column with hexane/2-propanol/methanol (97.5:2.0:0.5, v/v/v) plus 0.5% diethylamine as the mobile phase, and UV detection at 248 and 273 nm. The HF-LPME optimized conditions involved: n-octanol as the organic solvent, 0.2 mol/L acetic acid as the acceptor phase, donor phase pH adjusted to 13, sample agitation at 1500 rpm and extraction for 30 min. By using this extraction procedure, the recovery rates were in the range of 63-69%. The method was linear over the concentration range of 100-5000 ng/mL for each enantiomer of 1'-Oxo-BF (r>0.9978) and of 100-2500 ng/mL for each stereoisomer of 1'-OH-BF (r>0.9957). The quantification limits were 100 ng/mL for all analytes. The validated method was used to assess the in vitro biotransformation of bufuralol using rat liver microsomal fraction that demonstrated predominant formation of (S)-1'-Oxo-BF and (R,R)-1'-OH-BF.

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Section: Resultsmentioning

confidence: 99%

Stereoselective liquid chromatographic determination of 1′‐oxobufuralol and 1′‐hydroxybufuralol in rat liver microsomal fraction using hollow‐fiber liquid‐phase microextraction for sample preparation

Barth

Simões

Pupo

et al. 2011

J of Separation Science

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“…Therefore, to determine the elution order of DPZ metabolites, a combination of chromatographic and CD methods was used [25,26]. Hence, the CD spectra of 5-ODD and 6-ODD enantiomers were compared with the CD spectra of DPZ enantiomers.…”

Section: Elution Order Determinationmentioning

confidence: 99%

Chiral HPLC analysis of donepezil, 5-O-desmethyl donepezil and 6-O-desmethyl donepezil in culture medium: application to fungal biotransformation studies

et al. 2012

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An high performance liquid chromatography (HPLC) method for the enantioselective determination of donepezil (DPZ), 5-O-desmethyl donepezil (5-ODD), and 6-O-desmethyl donepezil (6-ODD) in Czapek culture medium to be applied to biotransformation studies with fungi is described for the first time. The HPLC analysis was carried out using a Chiralpak AD-H column with hexane/ethanol/methanol (75:20:5, v/v/v) plus 0.3 % triethylamine as mobile phase and UV detection at 270 nm. Sample preparation was carried out by liquid-liquid extraction using ethyl acetate as extractor solvent. The method was linear over the concentration range of 100-10,000 ng mL(-1) for each enantiomer of DPZ (r ≥ 0.9985) and of 100-5,000 ng mL(-1) for each enantiomer of 5-ODD (r ≥ 0.9977) and 6-ODD (r ≥ 0.9951). Within-day and between-day precision and accuracy evaluated by relative standard deviations and relative errors, respectively, were lower than 15 % for all analytes. The validated method was used to assess DPZ biotransformation by the fungi Beauveria bassiana American Type Culture Collection (ATCC) 7159 and Cunninghamella elegans ATCC 10028B. Using the fungus B. bassiana ATCC 7159, a predominant formation of (R)-5-ODD was observed while for the fungus C. elegans ATCC 10028B, DPZ was biotransformed to (R)-6-ODD with an enantiomeric excess of 100 %.

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“…Enantioselective resolution of 2 was achieved by enantioselective preparative HPLC as described. 23 The carbon analogs (6 and 7) were prepared starting with the conversion of ethyl 2-bromohexanoate into its phosphonate derivative by an Arbuzov reaction (Scheme 2). The product was coupled by a Wittig-Horner reaction to the aldehyde group of a precursor derived from 4-hydroxybenzaldehyde.…”

Section: Chemistrymentioning

confidence: 99%

Identification of 2-mercaptohexanoic acids as dual inhibitors of 5-lipoxygenase and microsomal prostaglandin E2 synthase-1

Zettl¹,

Koeberle²,

Pergola³

et al. 2011

Bioorganic & Medicinal Chemistry

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Enantiomer separation and indirect chromatographic absolute configuration prediction of chiral pirinixic acid derivatives: Limitations of polysaccharide-type chiral stationary phases in comparison to chiral anion-exchangers

Cited by 19 publications

References 46 publications

Stereoselective liquid chromatographic determination of 1′‐oxobufuralol and 1′‐hydroxybufuralol in rat liver microsomal fraction using hollow‐fiber liquid‐phase microextraction for sample preparation

Stereoselective liquid chromatographic determination of 1′‐oxobufuralol and 1′‐hydroxybufuralol in rat liver microsomal fraction using hollow‐fiber liquid‐phase microextraction for sample preparation

Chiral HPLC analysis of donepezil, 5-O-desmethyl donepezil and 6-O-desmethyl donepezil in culture medium: application to fungal biotransformation studies

Identification of 2-mercaptohexanoic acids as dual inhibitors of 5-lipoxygenase and microsomal prostaglandin E2 synthase-1

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