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Fractionation of low-molecular-mass heparin by centrifugal partition chromatography in the ion-exchange displacement mode

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Fractionation of low-molecular-mass heparin by centrifugal partition chromatography in the ion-exchange displacement mode ( fractionation-low-molecular-mass-heparin-by-centrifugal-part )

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a Abstract Journal of Chromatography A, 918 (2001) 47–57 Fractionation of low-molecular-mass heparin by centrifugal partition chromatography in the ion-exchange displacement mode Olivier Intesa, Jean-Hugues Renaulta,*, C. Sinquinb, Monique Ze`ches-Hanrota, a Jean-Marc Nuzillard Laboratoire de Pharmacognosie, UPRES-A CNRS 6013, CPCBAI, BP 1039, Moulin de la Housse, F-51097 Reims Cedex, France b Centrifugal partition chromatography in the ion-exchange displacement mode allowed a preparative and efficient fractionation of low-molecular-mass heparins from enoxaparin sodium. Amberlite LA2 — a lipophilic liquid secondary amine — was chosen as a weak anion exchanger. The biphasic system methyl isobutyl ketone–water was selected. 12 Protonated LA2 (10%, v/v) was added to the organic stationary phase. Hydroxide (Na , OH ) was chosen as a displacer in the aqueous mobile phase. The observed pH and concentration profiles are typical of displacement chromatography, as supported by numerical simulation. The Dubois test for the analysis of sugar content and an analysis of sulfur content (and consequently sulfatation rate) were carried out to monitor the effectiveness of the procedure. Moreover, the fractions were 1 analyzed by high-performance size-exclusion chromatography and the H NMR spectra confirmed the fractionation of the sample of enoxaparin sodium.  2001 Elsevier Science B.V. All rights reserved. Keywords: Heparin; Carbohydrates; Glycosaminoglycans; Enoxaparin sodium; Centrifugal partition chromatography URM2, Lab. VP/BM, IFREMER, Rue de l’Ile d’Yeu, BP 21105, F-44311 Nantes Cedex 3, France Received 7 December 2000; received in revised form 7 March 2001; accepted 8 March 2001 1. Introduction Enoxaparin sodium (Lovenox) is the commercial name of the substance obtained by alkaline hy- drolysis of heparin benzylic esters. It contains a complex mixture of low-molecular-mass heparins. These molecules are polysulfated polysaccharides. They belong to the family of glycosaminoglycans: a highly sulfated linear sugar chain composed of repeated disaccharidic units of uronic acids and *Corresponding author. Tel.: 133-3-2691-3548; fax: 133-3- 2691-3596. E-mail address: jh.renault@univ-reims.fr (J.-H. Renault). glycosamine. In this pattern four positions can be sulfated as shown in Fig. 1. Enoxaparin sodium contains on average eight dissacharide units with a mean molecular mass of 4500 Da (mostly comprised between 2000 and 8000 Da). Its antithrombotic and anticoagulant properties, inherited from heparins, confer on it a fundamental significance in surgery and medicine. Its fractiona- tion and characterization have proved to be difficult. Different techniques have been used to analyze and/ or fractionate heparins such as size-exclusion chro- matography [1], ion-exchange chromatography on solid support [2], capillary electrophoresis [3], or counter-current chromatography in the elution mode [4,5]. Ion-exchange centrifugal partition chromatog- 0021-9673/01/$ – see front matter  2001 Elsevier Science B.V. All rights reserved. PII: S0021-9673(01)00743-9 www.elsevier.com / locate / chroma

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