Determination of Enantiomeric Purity and Absolute Configuration by<scp>NMR</scp>Spectroscopy

Wenzel, Thomas J.

doi:10.1002/9781118596784.ssd050

Cited by 3 publications

(2 citation statements)

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“…Nuclear magnetic resonance (NMR) spectroscopy is a pivotal analytical technique for assessing enantiomeric purity and determining the absolute configuration of compounds, and its utility has been well documented in various studies (Wenzel 2013 ). In exploring the chiral distinctions between the erythro - ( d -KDGlc) and threo -forms (KDGal) of 2-keto-3-deoxy-hexonate, 1 H-NMR spectroscopy has proven particularly insightful, enabling clear differentiation of these stereoisomers (Sakamoto et al 2023 ; Yun et al 2015 ).…”

Section: Stereospecific Methods For Discrimination Of Enantiomersmentioning

confidence: 99%

Catabolism of 2-keto-3-deoxy-galactonate and the production of its enantiomers

Yun,

Lee,

Kim

et al. 2024

Appl Microbiol Biotechnol

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2-Keto-3-deoxy-galactonate (KDGal) serves as a pivotal metabolic intermediate within both the fungal d-galacturonate pathway, which is integral to pectin catabolism, and the bacterial DeLey-Doudoroff pathway for d-galactose catabolism. The presence of KDGal enantiomers, l-KDGal and d-KDGal, varies across these pathways. Fungal pathways generate l-KDGal through the reduction and dehydration of d-galacturonate, whereas bacterial pathways produce d-KDGal through the oxidation and dehydration of d-galactose. Two distinct catabolic routes further metabolize KDGal: a nonphosphorolytic pathway that employs aldolase and a phosphorolytic pathway involving kinase and aldolase. Recent findings have revealed that l-KDGal, identified in the bacterial catabolism of 3,6-anhydro-l-galactose, a major component of red seaweeds, is also catabolized by Escherichia coli, which is traditionally known to be catabolized by specific fungal species, such as Trichoderma reesei. Furthermore, the potential industrial applications of KDGal and its derivatives, such as pyruvate and d- and l-glyceraldehyde, are underscored by their significant biological functions. This review comprehensively outlines the catabolism of l-KDGal and d-KDGal across different biological systems, highlights stereospecific methods for discriminating between enantiomers, and explores industrial application prospects for producing KDGal enantiomers. Key points • KDGal is a metabolic intermediate in fungal and bacterial pathways • Stereospecific enzymes can be used to identify the enantiomeric nature of KDGal • KDGal can be used to induce pectin catabolism or produce functional materials

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Section: Stereospecific Methods For Discrimination Of Enantiomersmentioning

confidence: 99%

Catabolism of 2-keto-3-deoxy-galactonate and the production of its enantiomers

Yun,

Lee,

Kim

et al. 2024

Appl Microbiol Biotechnol

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“…Several separation methods and spectral techniques for the analysis of chiral compounds are available including high performance liquid chromatography (HPLC) [ 4 ], gas chromatography (GC) [ 5 ], thin layer chromatography (TLC) [ 6 ], supercritical fluid chromatography (SFC) [ 7 ], nuclear magnetic resonance spectroscopy (NMR) [ 8 ], circular dichroism spectroscopy or X-ray crystallography [ 9 ]. HPLC is the first-choice technique in the routine analysis of chiral pharmaceuticals; however, CE proved to be in the last decades a viable alternative and a complementary method.…”

Section: Introductionmentioning

confidence: 99%

The Use of Dual Cyclodextrin Chiral Selector Systems in the Enantioseparation of Pharmaceuticals by Capillary Electrophoresis: An Overview

et al. 2021

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Cyclodextrin (CD) derivatives are the most efficient and frequently used chiral selectors (CSs) in capillary electrophoresis (CE). There are situations when the use of a single CD as CS is not enough to obtain efficient chiral discrimination of the enantiomers; in these cases, sometimes this problem can be resolved using a dual CD system. The use of dual CD systems can often dramatically enhance enantioseparation selectivity and can be applied for the separation of many analytes of pharmaceutical interest for which enantioseparation by CE with another CS systems can be problematic. Usually in a dual CD system an anionic CD is used together with a neutral one, but there are situations when the use of a cationic CD with a neutral one or the use of two neutral CDs or even two ionized CDs can be an efficient solution. In the current review we present general aspects of the use of dual CD systems in the analysis of pharmaceutical substances. Several examples of applications of the use of dual CD systems in the analysis of pharmaceuticals are selected and discussed. Theoretical aspects regarding the separation of enantiomers through simultaneous interaction with the two CSs are also explained. Finally, advantages, disadvantages, potential and new direction in this chiral analysis field are highlighted.

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