Ligand chromatography as a novel method for the investigation of mixed complexes: stereoselective effects in α-amino acid copper(II) complexes

Даванков, В. А.; Рогожин, С. В.

doi:10.1016/s0021-9673(00)95566-3

Cited by 249 publications

(120 citation statements)

References 9 publications

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“…Studies of the use of optically active supports such as starch, wool, lactose, and cellulose (10)(11)(12)(13)(14)(15)(16)(17) and, more recently, synthetic resin matrices (18)(19)(20)(21)(22)(23)(24)(25)(26) have yielded several successful resolution methods. Still, selection of the appropriate matrix required for resolution of a given pair of optical isomers is difficult and usually empirical.…”

Section: Discussionmentioning

confidence: 99%

Resolution of DL-Tryptophan by Affinity Chromatography on Bovine-Serum Albumin-Agarose Columns

Stewart

Doherty

1973

Proc. Natl. Acad. Sci. U.S.A.

125

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Bovine-serum albumin, known to have antipodal specificity in the binding of tryptophan, was selected as the affinity chromatographic matrix for the attempted chromatographic resolution of DL-tryptophan. Complete resolution was accomplished when DL-tryptophan was chromatographed on bovine-serum albuminsuccinoylaminoethyl-Sepharose.Resolution of optical isomers by conventional methods is frequently laborious and incomplete. The mechanical and chemical methods are empirical in nature, and in practice choosing the appropriate resolving agents and physical means of separation can be difficult. Resolutions based on highly specific biological properties have been limited to enzyme reactions, and these reactions always resulted in chemical modification of one of the isomers. Differential binding of some optical isomers by a few serum proteins has been reported. Examples include binding of DI-tryptophan to bovine-serum albumin (1) and dl-aldosterone to corticosteroid-binding globulin (2). It would seem that this property of steroselective binding of optical isomers by proteins could be used for resolution of some optical isomers. We have begun studies to investigate this possibility and report here the resolution of DL-tryptophan on affinity columns of bovine-serum albumin-succinoylaminoethyl-agarose. (5), in which dipeptides are formed by reaction of the tryptophan with -glutamic acid N-carboxyanhydride, the -glutamyl-D-tryptophan is separated from the L-glutamyl-L-tryptophan by ion-exchange chromatography, and each diastereomer is quantitated. LTryptophan content was determined by the method of Guilbault and Hieserman (6) with -amino-acid oxidase, and an Aminco fluoromicrophotometer with a CS 7-60 primary filter and a 47B, 2A combination secondary filter.The substituted agarose supports were prepared according to Cuatrecasas (7) with cyanogen bromide. The extent of coupling was determined from amino-acid analyses of hydrolysates of the support material, and coupling efficiencies of 5-6% were normally obtained. Chromatographic columns were packed with either bovine-serum albumin linked directly to the agarose beads (bovine-serum albumin-agarose), bovineserum albumin linked to the agarose beads by an ethylenediamine-succinic acid leash (bovine-serum albumin-succinoylaminoethyl-agarose), or defatted bovine-serum albumin linked to the agarose beads by the same leash (defatted bovine-serum albumin-succinoylaminoethyl-agarose). Control columns were packed with agarose or leashed agarose (no bovine-serum albumin) as appropriate. RESULTSPreliminary experiments in which bovine-serum albuminagarose columns were used for chromatography of DLtryptophan indicated that there was some resolution of the DI,-tryptophan on these columns. However, these columns did not give reproducible results, due to the fact that the column material seemed to be altered during regeneration. In contrast, chromatography of DL-tryptophan on either of the two leashed column materials was reproducible, and hence these column materials were used in...

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Section: Discussionmentioning

confidence: 99%

Resolution of DL-Tryptophan by Affinity Chromatography on Bovine-Serum Albumin-Agarose Columns

Stewart

Doherty

1973

Proc. Natl. Acad. Sci. U.S.A.

125

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“…Ligand-exchange chromatography (LEC) introduced by Davankov and Rogozhim [228] [229][230][231][232], a-alkyl and N-alkyl amino acids [232,233], amino acid derivatives [232], dipeptides [232], hydroxy acids [234] and thyroid hormones [235]. Subsequently, a large number of chiral LEC phases and their applications have been published [236][237][238].…”

Section: Chiral Imprinted Polymersmentioning

confidence: 99%

Chiral separation by chromatographic and electromigration techniques. A Review

Gübitz

Schmid

2001

Biopharm & Drug Disp

225

135

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This review gives a survey of different chiral separation principles and their use in high-performance liquid chromatography (HPLC), gas chromatography (GC), supercritical fluid chromatography (SFC), thin-layer chromatography (TLC), capillary electrophoresis (CE) and capillary electrochromatography (CEC) highlighting new developments and innovative techniques. The mechanisms of the different separation principles are briefly discussed and some selected applications are shown.

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“…Pioneering work in the field of chiral ligand-exchange was done by Davankov's group who introduced this principle in the late 1960s -early 1970s [1][2][3].…”

Section: Separation By Liquid Chromatographymentioning

confidence: 99%

Chiral Separation by Ligand Exchange

Gbitz¹,

Schmid²

2006

Chiral Separation Techniques

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The principle of chiral ligand-exchange, introduced by Davankov, has become a widely used technique for chiral separation in both chromatography and in electromigration techniques. This simple technique makes use of the formation of mixed metal chelate complexes between a chiral selector and both enantiomers of an analyte. In HPLC, the chiral selector can be either bonded to the stationary phase or added to the mobile phase. In CE the chiral selector is simply added to the electrolyte. A relatively new approach represents CEC, where capillaries contain a chiral stationary phase. More than thousand papers appeared in the field of chiral ligand-exchange. To cite all papers would require several books.The present article gives an overview of both milestones and our activities on chiral separation using the principle of ligand-exchange. Recent advances in chip technology for chiral separations and new approaches regarding improvement of detection sensitivity are mentioned.Keywords: ligand-exchange; chiral selectors; chemically bonded phases; dynamically coated phases; monolithic phases; HPLC; capillary electrophoresis; capillary electro chromatography ХИРАЛНИ РАЗДВОЈУВАЊА СО ИЗМЕНА НА ЛИГАНДИПринципот на измена на лиганди, воведен од Даванков, стана широко користена техника за хирални раздвојувања и во хроматографските и во електромиграциските техники. Оваа едноставна техника го користи образувањето на мешани металoхелатни комплекси помеѓу хирален селектор и обата енантиомерa на аналитот. Во високоефикасната течна хроматографија (HPLC) хиралниот селектор може да биде врзан на стационарната фаза или додаден во мобилната фаза. Во капиларната електрофореза (CE) хиралниот селектор едноставно се додава во електролитот. Капиларната електрохроматографија (CEC) претставува релативно нов пристап, каде што капиларите содржат хирална стационарна фаза. Објавени се повеќе од илјада трудови од областа на хирални раздвојувања со измена на лиганди и потребни би биле повеќе книги за сите тие да се соберат.Во овој труд е даден преглед на главните развојни точки и на нашата работа на хирални разделувања со употреба на принципот на измена на лиганди. Освен тоа, наведени се и последните достигнувања на чип-технологијата за хирални раздвојувања и новите пристапи поврзани со подобрување на осетливоста на детекцијата.Клучни зборови: измена на лиганди; хирални селектори; хемиски врзани фази; динамички нанесени фази; монолитни фази; HPLC; капиларна електрофореза; капиларна електрохроматографија MJCCA9 -576

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Ligand chromatography as a novel method for the investigation of mixed complexes: stereoselective effects in α-amino acid copper(II) complexes

Cited by 249 publications

References 9 publications

Resolution of DL-Tryptophan by Affinity Chromatography on Bovine-Serum Albumin-Agarose Columns

Resolution of DL-Tryptophan by Affinity Chromatography on Bovine-Serum Albumin-Agarose Columns

Chiral separation by chromatographic and electromigration techniques. A Review

Chiral Separation by Ligand Exchange

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