Resolution and determination of the enantiomeric purity and absolute configurations of α-aryl-α-hydroxymethanephosphonates

Pirkle, William H.; Brice, L. Jonathan; Widlanski, Theodore S.; Roestamadji, Juliatiek

doi:10.1016/0957-4166(96)00263-7

Cited by 29 publications

(5 citation statements)

References 5 publications

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“…Most often, indirect 31 P-NMR methods are used for these purposes [6]. While there have been published several reports on different enantioselective HPLC methods for the ester analogs of phosphonic and amino phosphonic acids, e.g., using cellulose or amylose based chiral stationary phases (CSPs( [7] or 'Pirkle-type' CSPs [8][9][10], the number of publications dealing with the direct enantioseparation of amino phosphonic acids with underivatized phosphonic acid is limited [7,[11][12][13]. Free 2-amino-o-phosphonoalkanoic acid enantiomers could be resolved on a chiral crown ether stationary phase [12] and aromatic aminophosphonic acids on an acetylatedb-cyclodextrin-bonded stationary phase [11].…”

Section: Introductionmentioning

confidence: 99%

Simultaneous separation of the stereoisomers of 1-amino-2-hydroxy and 2-amino-1-hydroxypropane phosphonic acids by stereoselective capillary electrophoresis employing a quinine carbamate type chiral selector

et al. 2001

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A stereoselective nonaqueous capillary electrophoresis (CE) method utilizing O-(tert-butylcarbamoyl) quinine as chiral ion-pair agent and additive to the non aqueous background electrolyte was evaluated for the simultaneous separation of the enantiomers and diastereomers of 1 -amino-2-hydroxypropane phosphonic acid besides the corresponding beta-aminophosphonic acid analogs, the stereoisomers of 2-amino-1-hydroxypropane phosphonic acid, in a single run. The separations have been carried out using the partial filling technique to avoid strong background signal from the quinine selector. It conveniently allowed the baseline separation of all eight components of interest (alpha- as well as beta-aminophosphonic acids) as N-2,4-dinitrophenyl derivatives in a single run. Moreover, the absolute configurations of all eight peaks were identified. Compared to the quinine carbamate selector, the corresponding 'pseudo-enantiomeric' O-(tert-butylcarbamoyl) quinidine selector exhibited reserved elution order and nearly identical resolutions. The proposed CE method turned out to be advantageous over stereoselective high-performance liquid chromatography (HPLC) with a quinine carbamate type stationary phase, which showed high enantioselectivity, but failed to simultaneously separate all eight components.

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Section: Introductionmentioning

confidence: 99%

Simultaneous separation of the stereoisomers of 1-amino-2-hydroxy and 2-amino-1-hydroxypropane phosphonic acids by stereoselective capillary electrophoresis employing a quinine carbamate type chiral selector

et al. 2001

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“…Later, the Whelk-O1 phase proved a broad-spectrum CSP for the separation of compounds bearing an aromatic system with a hydrogen-bond acceptor group located near the stereogenic center . It has been, thereafter, used in the last 20 years for the separation of many chiral compounds whose structure fits the general mechanism of separation, including alcohols, amides, esters, ethers, epoxides, carbamates, aldehydes, ketones, carboxylic acids, aziridines, phosphonates, and ureas. − The phase is commonly used under normal-phase (NP) conditions but interesting examples have been reported with water-rich mobile phases, , as well as in polar organic mode (POM) . Further applications include the use of supercritical/subcritical CO 2 solvent, − while its high loading capacity has been exploited in preparative LC. , The Whelk-O1 selector has also been used in Inverted Chirality Columns Approach to determine the enantiomeric excess of ( S )-namitecan (a water-soluble camptothecin derivative) in the absence of the minor enantiomer or the racemate as reference material …”

mentioning

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Introducing Enantioselective Ultrahigh-Pressure Liquid Chromatography (eUHPLC): Theoretical Inspections and Ultrafast Separations on a New Sub-2-μm Whelk-O1 Stationary Phase

et al. 2012

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A new chiral stationary phase for ultrahigh-pressure liquid chromatography (UHPLC) applications was prepared by covalent attachment of the Whelk-O1 selector to spherical, high-surface-area 1.7-μm porous silica particles. Columns of varying dimensions (lengths of 50, 75, 100, and 150 mm and internal diameters of 3.0 or 4.6 mm) were packed and characterized in terms of permeability, efficiency, retention, and enantioselectivity, using both organic and water-rich mobile phases. A conventional HPLC Whelk-O1 column based on 5.0-μm porous silica particles and packed in a 250 mm × 4.6 mm column was used as a reference. Van Deemter curves, generated with low-molecular-weight solutes on a 100 mm × 4.6 mm column packed with the 1.7-μm particles, showed H(min) (μm) and μ(opt) (mm/s) values of 4.10 and 5.22 under normal-phase and 3.74 and 4.34 under reversed-phase elution conditions. The flat C term of the van Deemter curves observed with the 1.7-μm particles allowed the use of higher-than-optimal flow rates without significant efficiency loss. Kinetic plots constructed from van Deemter data confirmed the ability of the column packed with the 1.7-μm particles to afford subminute separations with good efficiency and its superior performances in the high-speed regime, compared to the column packed with 5.0-μm particles. Resolutions in the time scale of seconds were obtained using a 50-mm-long column in the normal phase or polar organic mode. The intrinsic kinetic performances of 1.7-μm silica particles are retained in the Whelk-O1 chiral stationary phase, clearly demonstrating the potentials of enantioselective UHPLC in terms of high speed, throughput, and resolution.

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“…«WHELK-O 1» обладает лучшей селективностью благодаря увеличенной плотности пришивки, она оказалась подходящей для разделения энантиомеров широкого круга органических соединений. Описано разделение арилметанфосфонатов [15,16], γ-лактонов [17], N-арилоксазолинов, N-арилтиозолинов [18], ариламидов [19], арилкарбоновых кислот и оксикислот, арилкетонов, арилспиртов и олеиновых спиртов [20]. Хорошие энантиоселективные свойства «WHELK-O 1» по отношению к разным классам органических соединений использовали для разделения энантиомеров биологически активных соединений, входящих в состав ряда фармацевтических препаратов: нирванола, фталидомида, индапамида, тропикамида, бупивакаина, никардипина и пр.…”

Section: Introductionunclassified

Смешанные Хиральные Неподвижные Фазы В Хроматографии (Обзор)

Fedorova¹,

Shapovalova²,

Шпигун³

2018

sorpchrom

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Обсуждается использование смешанных селекторов в газовой и высокоэффективной жидкостной хроматографии для разделения оптических изомеров. Они позволяют повысить универсальность хиральной фазы. В газовой хроматографии широко и успешно используются смеси модифицированного β-циклодекстрина. В ВЭЖХ наиболее изучены смешанные хиральные селекторы на основенизкомолекулярных селекторов и производных полисахаридов, в меньшей степени ̶ белков и макроциклических антибиотиков.

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Resolution and determination of the enantiomeric purity and absolute configurations of α-aryl-α-hydroxymethanephosphonates

Cited by 29 publications

References 5 publications

Simultaneous separation of the stereoisomers of 1-amino-2-hydroxy and 2-amino-1-hydroxypropane phosphonic acids by stereoselective capillary electrophoresis employing a quinine carbamate type chiral selector

Simultaneous separation of the stereoisomers of 1-amino-2-hydroxy and 2-amino-1-hydroxypropane phosphonic acids by stereoselective capillary electrophoresis employing a quinine carbamate type chiral selector

Introducing Enantioselective Ultrahigh-Pressure Liquid Chromatography (eUHPLC): Theoretical Inspections and Ultrafast Separations on a New Sub-2-μm Whelk-O1 Stationary Phase

Смешанные Хиральные Неподвижные Фазы В Хроматографии (Обзор)

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