Separation of unmodified α-amino acid enantiomers by reverse phase HPLC

Davankov, V. A.; Bochkov, A. S.; Kurganov, A. A.; Roumeliotis, P.; Unger, Klaus K.

doi:10.1007/bf02303437

Cited by 213 publications

(64 citation statements)

References 11 publications

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“…The first dynamically coated chiral LE phases were described by Davankov et al [8]. A commercially available RP HPLC column was converted into a chiral LE column by simply pumping a solution of long-chain N-alkyl-L-4-hydroxyproline derivatives in methanol -water through the column.…”

Section: Introductionmentioning

confidence: 99%

Fast chiral separation by ligand‐exchange HPLC using a dynamically coated monolithic column

Schmid¹,

Schreiner

Reisinger

et al. 2006

J of Separation Science

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The preparation and application of dynamically coated ligand-exchange chromatography phases for enantioseparation is described. The phases were prepared by pumping a solution of N-decyl-L-4-hydroxyproline, N-hexadecyl-L-4-hydroxyproline, or N-2-hydroxydodecyl-L-4-hydroxyproline through a commercially available monolithic RP-18 column. These coatings are stable against desorption for months at ambient temperature when aqueous mobile phases are used. The columns were applied to the chiral separation of amino acids, glycyl dipeptides and diastereomeric dipeptides, and tripeptides. The chiral selector can be removed or changed easily by washing the column with ACN or methanol. Ultrafast separations in the range of seconds were achieved using high flow rates.

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Section: Introductionmentioning

confidence: 99%

Fast chiral separation by ligand‐exchange HPLC using a dynamically coated monolithic column

Schmid¹,

Schreiner

Reisinger

et al. 2006

J of Separation Science

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“…If ternary complexes with N-trans orientation related to central copper (II) ion are formed between 1 and the D enantiomer, the a-substituent of this enantiomer will be directed toward the Stern layer, an electric double layer. And if the a-substitutent is directed toward the hydrophobic surface like reversed-phase packings, this orientation could cause an increase in stabilization by means of hydrophobic interactions, as already discussed by Davankov et al [24,25] with regard to reversed-phase packings coated with N-alkyl-L-hydroxyproline and copper (II) ion, the explanation for the elution order was that L-amino acids are eluted faster than Damino acids by the additional hydrophobic interaction. However, this explanation cannot be applied straightforward to our separation system.…”

Section: Introductionmentioning

confidence: 91%

“…This situation is similar to that found in reversed-phase liquid chromatography aiming at separating enantiomers by metal chelate complexation. In reversed-phase liquid chromatography, chiral ligands with long alkyl chains are hydrophobically anchored onto the surface of packing, interact with central metals and form diastereomeric ternary complexes among the chiral ligand, central metal and enantiomeric solutes [23][24][25]. This is one of the most powerful approaches for separation of enantiomers of amino acids.…”

Section: Introductionmentioning

confidence: 99%

Chiral separation of dansyl-DL-amino acids with micellar systems containing copper (II) ion andN-n-dodecyl-L-proline in electrokinetic capillary chromatography

Dobashi

Hamada

1999

Electrophoresis

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“…The aqueous phase of the enzymatic cteavage solution was worked up to give L-2-acetamido-4-chlorophenylacetic acid as described previously (yield was 7.3 g, or 103.4% of theoretical):…”

Section: Enzymatic Hydrolysis Of ~~-2-acetamido-4-chlorophen Ylaceticmentioning

confidence: 99%

Preparation of optically activeD‐arylglycines for use as side chains for semisynthetic penicillins and cephalosporins using immobilized subtilisins in two‐phase systems

Schutt

Schmidt-Kastner

Arens

et al. 1985

Biotech & Bioengineering

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Optically active D-arylglycines, which are of interest for preparation of semisynthetic penicillins and cephalosporins, were isolated from the racemic mixtures of their derivatives using immobilized proteolytic enzyme subtilisin (EC No. 3.4.4. 16). The performance of these reactions in two-phase systems, consisting of water and an immiscible organic solvent, improved the yield, purity, and economics of the process by increasing the substrate solubility and reducing the rate of nonenzymatic hydrolysis. The proportion of the organic phase can be as much as 75% of the overall volume without seriously impairing the enzymatic activity. The optically pure D-and L-arylglycines were liberated from their D- and L-derivatives by acid hydrolysis. The substituent influence of the various arylglycine derivatives on the rate of the enzymatic cleavage reaction was investigated.

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Separation of unmodified α-amino acid enantiomers by reverse phase HPLC

Cited by 213 publications

References 11 publications

Fast chiral separation by ligand‐exchange HPLC using a dynamically coated monolithic column

Fast chiral separation by ligand‐exchange HPLC using a dynamically coated monolithic column

Chiral separation of dansyl-DL-amino acids with micellar systems containing copper (II) ion andN-n-dodecyl-L-proline in electrokinetic capillary chromatography

Preparation of optically activeD‐arylglycines for use as side chains for semisynthetic penicillins and cephalosporins using immobilized subtilisins in two‐phase systems

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