Evaluation of the macrocyclic glycopeptide A-40,926 as a high-performance liquid chromatographic chiral selector and comparison with teicoplanin chiral stationary phase

Berthod, Alain; Yu, Timothy; Kullman, John P.; Armstrong, Daniel W.; Gasparrini, Francesco; D’Acquarica, Ilaria; Misiti, D.; Carotti, Angelo

doi:10.1016/s0021-9673(00)00804-9

Cited by 53 publications

(23 citation statements)

References 19 publications

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“…Avoparcin, has recently been introduced as a chiral selector and was demonstrated to have chiral recognition properties complementary to the other macrocyclic antibiotics [134]. Recently, a new CSP containing the macrocyclic glycopeptide A-40 926 was introduced and compared regarding its chiral recognition ability with the teicoplanin phase [142,143]. Acquarica studied different immobilization procedures for teicoplanin comparing different silica gel supports [144].…”

Section: Direct Methodsmentioning

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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Section: Direct Methodsmentioning

confidence: 99%

Chiral separation by chromatographic and electromigration techniques. A Review

Gübitz

Schmid

2001

Biopharm & Drug Disp

225

135

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“…Furthermore, MCPPM and DCPPM were better resolved on the native teicoplanin CSPs with 20% MeOH/80% aqueous buffer (pH 4.1 by TEAA, 1%). However, the resolution for bromacil with a pyrimidinedione ring was higher on teicoplanin structurally related A-40926 CSP than on teicoplanin CSP (R s 2.8 vs. R s 2.5) (Berthod et al, 2000b). Rac-diclofop methyl and rac-diclofop acid were baseline separated on a chiralcel OJ-H column using chiral HPLC coupled with fluorescence detection with a mobile phase of Hex/IPA/HAc (90:10:0.2, v/v) at a flow rate of 0.5 mL/min under 20 °C (Lin et al, 2006) while in a report by Zhou et al (Gu et al, 2010), they were completely resolved on CDMPC CSP with Hex/IPA(98:2) containing 0.1% TFA as mobile phase by HPLC-DAD.…”

Section: Enantioseparation and Enantioselective Analysis Of Chiral Hementioning

confidence: 88%

Enantioseparation and Enantioselective Analysis of Chiral Herbicides

Jin¹,

Gao²,

Li³

et al. 2011

Herbicides, Theory and Applications

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“…The cyclic antibiotics (avoparcin, teicoplanin, ristocetin A and vancomycin analogs) can be attached to silica gel via epoxy-terminated organosilanes, as described earlier for cyclodextrins [11], or they can be immobilized by reacting the macrocycle with an isocyanate-terminated organosilane in anhydrous dimethyl formamide. A-40,929 and teicoplanin aglycone were covalently grafted to a silica surface via a bifunctional aliphatic isocyanate (1,6-diisocyanatohexane) [21,22,39]. Norvancomycin was linked to silica gel via one spacer with different functionalities at the opposite terminal, e. g. isothiocyanate at one end, and triethoxysilane at the other [48].…”

Section: Binding the Selector To Silica Gelmentioning

confidence: 99%

HPLC separation of amino acid enantiomers and small peptides on macrocyclic antibiotic‐based chiral stationary phases: A review

Ilisz

Berkecz

Péter

2006

J of Separation Science

158

105

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The search for new and effective chiral selectors capable of separating a wide variety of enantiomeric compounds is an ongoing process. In the past decade, macrocyclic antibiotics have proved to be an exceptionally useful class of chiral selectors for the separation of enantiomers of biological and pharmacological importance by means of HPLC, TLC and electrophoresis. More chiral analytes have been resolved through the use of glycopeptides than with all the other macrocyclic antibiotics combined (ansamycins, thiostrepton, aminoglycosides, etc.). The glycopeptides avoparcin, teicoplanin, ristocetin A and vancomycin have been extensively used as chiral selectors in the form of chiral bonded phases in HPLC, and HPLC stationary phases based on these glycopeptides have been commercialized. Teicoplanin, vancomycin, their analogs and ristocetin A seem to be the most useful glycopeptide HPLC bonded phases for the enantioseparation of proteins and unusal native and derivatized amino acids. In fact, the macrocyclic glycopeptides are to some extent complementary to one another: where partial enantioresolution is obtained with one glycopeptide, there is a high probability that baseline or better separation can be obtained with another. This review sets out to characterize the physicochemical properties of these antibiotics and their application in the enantioseparations of amino acids. The mechanism of separation, the sequence of elution of the stereoisomers and the relation to the absolute configuration are also discussed.

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Evaluation of the macrocyclic glycopeptide A-40,926 as a high-performance liquid chromatographic chiral selector and comparison with teicoplanin chiral stationary phase

Cited by 53 publications

References 19 publications

Chiral separation by chromatographic and electromigration techniques. A Review

Chiral separation by chromatographic and electromigration techniques. A Review

Enantioseparation and Enantioselective Analysis of Chiral Herbicides

HPLC separation of amino acid enantiomers and small peptides on macrocyclic antibiotic‐based chiral stationary phases: A review

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