Determination of the Degree of Esterification in Heparin Benzylates During Synthesis of Enoxaparin, a Domestic Analog of Low-Molecular-Mass Heparin

L. E. Frumin; K. P. Yur’eva; A. V. Matveev; E. V. Vorfolomeeva; I. A. Vostrov; G. V. Zatonskii; D. I. Prokhorov; E. S. Zhavoronok; A. V. Panov; L. E. Grebenkina; N. V. Pyatigorskaya; G. É. Brkich; S. A. Kedik

doi:10.1007/s11094-019-02089-7

Determination of the Degree of Esterification in Heparin Benzylates During Synthesis of Enoxaparin, a Domestic Analog of Low-Molecular-Mass Heparin

Authors: Frumin L.E.¹, Yur’eva K.P.¹, Matveev A.V.¹, Vorfolomeeva E.V.¹^,2, Vostrov I.A.², Zatonskii G.V.³, Prokhorov D.I.¹, Zhavoronok E.S.¹^,2, Panov A.V.¹^,2, Grebenkina L.E.¹, Pyatigorskaya N.V.⁴, Brkich G.É.⁴, Kedik S.A.¹^,2
Affiliations:
1. M. V. Lomonosov Institute of Fine Chemical Technologies, Russian Technological University
2. Institute of Pharmaceutical Technologies
3. G. F. Gause Institute of New Antibiotics
4. I. M. Sechenov First Moscow State Medical University (Sechenov University), Ministry of Health of Russia
Issue: Vol 53, No 9 (2019)
Pages: 852-857
Section: Article
URL: https://journals.rcsi.science/0091-150X/article/view/246033
DOI: https://doi.org/10.1007/s11094-019-02089-7
ID: 246033

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Abstract

The esterification stage of low-molecular-mass heparin (enoxaparin) production by hydrolytic depolymerization of unfractionated heparin was studied and consisted of treating previously synthesized benzethonium heparinate with benzyl chloride. The content of benzyl moieties in the synthesized heparin benzylates and their degree of benzylation were determined using HPLC, PMR, and ¹³C NMR methods. A carboxylic-acid content of 0.13 ± 0.01 mol/g in the starting heparin was calculated from these results. A new method for estimating the degree of heparin benzylation from PMR and HPLC data was proposed. The benzyl content in the heparin benzylates increased with increasing molar excess of benzyl chloride.

Keywords

low-molecular-mass heparin, enoxaparin, degree of benzylation, benzethonium heparinate, heparin benzylate, unfractionated heparin

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Determination of the Degree of Esterification in Heparin Benzylates During Synthesis of Enoxaparin, a Domestic Analog of Low-Molecular-Mass Heparin

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Abstract

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About the authors

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