Resolution of Optical Isomers by Gas Liquid Partition Chromatography

Gil‐Av, E.; Charles-Sigler, Rosita; Fischer, G.; Nurok, David

doi:10.1093/chromsci/4.2.51

Cited by 87 publications

(15 citation statements)

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“…Mixtures of diastereomers can be resolved by gas chromatography (Gil-Av and Nurok 1975) or HPLC (Eberhardt et al 1974) using an achiral column. We were able to resolve the diastereomeric D-and L-alanine esters of D-IpI by reversephase HPLC.…”

Section: Discussionmentioning

confidence: 99%

Stereoselective aminoacylation of a dinucleoside monophosphate by the imidazolides ofDl-alanine and N-(tert-butoxycarbonyl)-Dl-alanine

Profy

Usher

1984

J Mol Evol

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The aminoacylation of diinosine monophosphate (IpI) was studied. When the acylating agent was the imidazolide of N-(tert-butoxycarbonyl)-DL-alanine, a 40% enantiomeric excess of the L isomer was incorporated at the internal 2' site and the positions of equilibrium for the 2' in equilibrium with 3' migration reaction differed for the D and L enantiomers. The reactivity of the nucleoside hydroxyl groups decreased in the order 2'(3') greater than internal 2' greater than 5', and the extent of reaction was affected by the concentration of the imidazole buffer (pH 7.1). In contrast, reaction of IpI with the imidazolide of unprotected DL-alanine led to an excess of the D isomer at the internal 2' site, while reaction with the N-carboxy anhydride of DL-alanine proceeded without detectable stereoselection. The relevance of these results to the evolution of optical activity and the origin of genetically directed protein synthesis is discussed.

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Section: Discussionmentioning

confidence: 99%

Stereoselective aminoacylation of a dinucleoside monophosphate by the imidazolides ofDl-alanine and N-(tert-butoxycarbonyl)-Dl-alanine

Profy

Usher

1984

J Mol Evol

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“…The amino acids were converted into isopropyl-N-trifluoroacetyl (TFA) derivatives [16] in two steps. First, a 1.25 N solution (1 ml) of SOC12 in isopropanol [17] was added to the sample in a screwcapped vial, filled with nitrogen, and heated for 1 hour at 100°C.…”

Section: Gas Chromatographymentioning

confidence: 99%

Racemization of aspartic acid in the extracellular matrix proteins of primary and secondary dentin

1993

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The accumulation with age of D-aspartic acid in primary and secondary human dentin was determined. In primary dentin, the plot of the D/L Asp ratio vs. age was found to fit first-order kinetics in accordance with the literature. But the secondary dentin behaved in an irregular manner and showed, in the great majority of cases, significantly increased D/L Asp ratios. Possible reasons for these findings, such as differences in protein composition and/or in the prevailing temperature, are discussed.

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“…Resolution of the diasteriomers formed by a variety of methods has been reviewed recently. 6 In a previous communication we reported the synthesis of PFBPI and its utilization as a chiral derivatizing reagent for the qualitative estimation of the enantiomeric composition of optically active amine compound^.^ Application of this qualitative method to measure amphetamine quantitatively from biological fluids was not successful due to excessive interference from endogenous compounds.…”

Section: Resultsmentioning

confidence: 99%

Quantitative determination of enantiomeric compounds. I—simultaneous measurement of the optical isomers of amphetamine in human plasma and saliva using chemical ionization mass spectrometry

Matin¹,

Wan

Knight

1977

Biol. Mass Spectrom.

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A sensitive and specific method for the quantitative determination of the optical isomers of amphetamine from human plasma and saliva is described. Amphetamine was extracted from basified plasma or saliva with hexane and then derivatized by reaction with N-pentafluorobenzoyl-S-(-)-prolyl-1-imidazolide. The reaction of the amphetamine enantiomers with this chiral reagent yields diasteriomers which are easily resolved by gas liquid chromatography. The resolved diasteriomers upon elution from the gas chromatograph were measured quantitatively by chemical ionization mass spectrometry. Plasma and saliva levels achieved following the oral administration of 10 mg of dl-, d- and l-amphetamine in man are reported.

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Resolution of Optical Isomers by Gas Liquid Partition Chromatography

Cited by 87 publications

References 0 publications

Stereoselective aminoacylation of a dinucleoside monophosphate by the imidazolides ofDl-alanine and N-(tert-butoxycarbonyl)-Dl-alanine

Stereoselective aminoacylation of a dinucleoside monophosphate by the imidazolides ofDl-alanine and N-(tert-butoxycarbonyl)-Dl-alanine

Racemization of aspartic acid in the extracellular matrix proteins of primary and secondary dentin

Quantitative determination of enantiomeric compounds. I—simultaneous measurement of the optical isomers of amphetamine in human plasma and saliva using chemical ionization mass spectrometry

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