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30 results on '"Kellenbach, Edwin"'

9. Selective Binding of Heparin/Heparan Sulfate Oligosaccharides to Factor H and Factor H-Related Proteins: Therapeutic Potential for C3 Glomerulopathies

Author

Loeven, Markus A., primary, Maciej-Hulme, Marissa L., additional, Yanginlar, Cansu, additional, Hubers, Melanie C., additional, Kellenbach, Edwin, additional, de Graaf, Mark, additional, van Kuppevelt, Toin H., additional, Wetzels, Jack, additional, Rabelink, Ton J., additional, Smith, Richard J. H., additional, and van der Vlag, Johan, additional

Published
2021
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10. Selective Binding of Heparin/Heparan Sulfate Oligosaccharides to Factor H and Factor H-Related Proteins: Therapeutic Potential for C3 Glomerulopathies

Author

Loeven, M.A., Maciej Hulme, M.L., Yanginlar, C., Hubers, Melanie C., Kellenbach, Edwin, Graaf, M.J.J. de, Kuppevelt, T.H. van, Wetzels, J.F.M., Smith, R.J., Vlag, J. van der, Loeven, M.A., Maciej Hulme, M.L., Yanginlar, C., Hubers, Melanie C., Kellenbach, Edwin, Graaf, M.J.J. de, Kuppevelt, T.H. van, Wetzels, J.F.M., Smith, R.J., and Vlag, J. van der

Abstract

Contains fulltext : 237318.pdf (Publisher’s version ) (Open Access)

Published
2021

12. The conformation of the idopyranose ring revisited: How subtle O-substituent induced changes can be deduced from vicinal H-1-NMR coupling constants

Author

Haasnoot, Cornelis A.G., de Gelder, René, Kooijman, Huub, Kellenbach, Edwin R., Crystal and Structural Chemistry, and Sub Crystal and Structural Chemistry

Subjects
Cyclohexane conformation, Substituent, Solid State Chemistry, 010402 general chemistry, 01 natural sciences, Biochemistry, X-ray data, Analytical Chemistry, chemistry.chemical_compound, Heparin constituents, Conformational isomerism, chemistry.chemical_classification, Coupling constant, Conformational equilibrium, Sugar code, 010405 organic chemistry, Chemistry, Six-membered ring puckering, Intermolecular force, Organic Chemistry, Glycosidic bond, General Medicine, 0104 chemical sciences, Crystallography, Glycosaminoglycan, Proton NMR, Vicinal
Abstract

The idopyranose ring plays a pivotal role in the conformational, dynamical, and intermolecular binding aspects of glycosaminoglycans like heparin and dermatan sulfate and it was early on assigned a role in the Sugar Code governing biological recognition processes. There is consensus that next to the two canonical 1C4 and 4C1 chair conformations, the conformational space accessible to the idopyranose ring entails a 2SO skew-boat conformation, but the equilibrium between these three ring puckers has evaded satisfactory quantification. In this study a meta-analysis of X-ray solid-state data and vicinal NMR coupling constants is presented, based on the Truncated Fourier Puckering (TFP) formalism and the generalized Karplus (CAGPLUS) equation. This approach yields a model-free, granular and consistent reckoning of 159 idopyranose solution puckering equilibria studied by NMR and allows us to reproduce the involved 636 NMR vicinal couplings with an overall residual RMS(Jobs-Jcalc) of 0.184 Hz. Our analyses show that for all ring systems examined, the idopyranosyl chair conformations take up the same ring pucker irrespective of the ring substituent pattern or a vast variety in experimental conditions. Instead, it is the (skew-)boat conformation that adapts to the substitution pattern of the idopyranose ring or a specific sulfation pattern of neighboring saccharides. All idopyranose rings are involved in conformational equilibria that subsume the aforementioned conformers which turn out to differ only a few kJ/mole in conformational energy. Thus, the plasticity and flexibility of idopyranose remains intact under practically all circumstances and, as the glycosidic linkages in heparin are considered to be relatively stiff, the iduronic moiety functions as the linchpin of heparin flexibility thereby being rather a “space(r)” than a “letter” in the alleged Sugar Code alphabet.

Published
2020

15. Extended Physicochemical Characterization of the Synthetic Anticoagulant Pentasaccharide Fondaparinux Sodium by Quantitative NMR and Single Crystal X-ray Analysis

Author

Wildt, William de, Kooijman, Huub, Funke, Carel, Üstün, Bülent, Leika, Afranina, Lunenburg, Maarten, Kaspersen, Frans, Kellenbach, Edwin, Crystal and Structural Chemistry, and Crystal and Structural Chemistry

Subjects
0301 basic medicine, Magnetic Resonance Spectroscopy, Fondaparinux sodium, extended physicochemical characterization, qNMR, single crystal X-ray structure, reference standard, iduronic acid conformation, Arixtra®, Stereochemistry, Cyclohexane conformation, Antithrombin III, Molecular Conformation, Pharmaceutical Science, Oligosaccharides, Iduronic acid, Fondaparinux, Crystallography, X-Ray, Article, Analytical Chemistry, lcsh:QD241-441, 03 medical and health sciences, chemistry.chemical_compound, lcsh:Organic chemistry, Polysaccharides, Drug Discovery, medicine, Humans, Physical and Theoretical Chemistry, Binding Sites, Anticoagulant drug, Chemistry, Heparin, Organic Chemistry, Antithrombin, Absolute configuration, Anticoagulants, Blood Coagulation Disorders, Fondaparinux Sodium, Crystallography, 030104 developmental biology, Chemistry (miscellaneous), Molecular Medicine, Single crystal, medicine.drug
Abstract

Fondaparinux sodium is a synthetic pentasaccharide representing the high affinity antithrombin III binding site in heparin. It is the active pharmaceutical ingredient of the anticoagulant drug Arixtra(®). The single crystal X-ray structure of Fondaparinux sodium is reported, unequivocally confirming both structure and absolute configuration. The iduronic acid adopts a somewhat distorted chair conformation. Due to the presence of many sulfur atoms in the highly sulfated pentasaccharide, anomalous dispersion could be applied to determine the absolute configuration. A comparison with the conformation of Fondaparinux in solution, as well as complexed with proteins is presented. The content of the solution reference standard was determined by quantitative NMR using an internal standard both in 1999 and in 2016. A comparison of the results allows the conclusion that this method shows remarkable precision over time, instrumentation and analysts.

Published
2017

16. Extended Physicochemical Characterization of the Synthetic Anticoagulant Pentasaccharide Fondaparinux Sodium by Quantitative NMR and Single Crystal X-ray Analysis

Author

Crystal and Structural Chemistry, Wildt, William de, Kooijman, Huub, Funke, Carel, Üstün, Bülent, Leika, Afranina, Lunenburg, Maarten, Kaspersen, Frans, Kellenbach, Edwin, Crystal and Structural Chemistry, Wildt, William de, Kooijman, Huub, Funke, Carel, Üstün, Bülent, Leika, Afranina, Lunenburg, Maarten, Kaspersen, Frans, and Kellenbach, Edwin

Published
2017

18. Extended Physicochemical Characterization of the Synthetic Anticoagulant Pentasaccharide Fondaparinux Sodium by Quantitative NMR and Single Crystal X-ray Analysis.

Author

de Wildt, William, Kooijman, Huub, Funke, Carel, Üstün, Bülent, Leika, Afranina, Lunenburg, Maarten, Kaspersen, Frans, and Kellenbach, Edwin

Subjects
SODIUM compounds, NUCLEAR magnetic resonance, SINGLE crystals, X-ray diffraction, HEPARIN
Abstract

Fondaparinux sodium is a synthetic pentasaccharide representing the high affinity antithrombin III binding site in heparin. It is the active pharmaceutical ingredient of the anticoagulant drug Arixtra®. The single crystal X-ray structure of Fondaparinux sodium is reported, unequivocally confirming both structure and absolute configuration. The iduronic acid adopts a somewhat distorted chair conformation. Due to the presence of many sulfur atoms in the highly sulfated pentasaccharide, anomalous dispersion could be applied to determine the absolute configuration. A comparison with the conformation of Fondaparinux in solution, as well as complexed with proteins is presented. The content of the solution reference standard was determined by quantitative NMR using an internal standard both in 1999 and in 2016. A comparison of the results allows the conclusion that this method shows remarkable precision over time, instrumentation and analysts. [ABSTRACT FROM AUTHOR]

Published
2017
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19. From Farm to Pharma: An Overview of Industrial Heparin Manufacturing Methods.

Author

van der Meer, Jan-Ytzen, Kellenbach, Edwin, and van den Bos, Leendert J.

Subjects
*HEPARIN, *ANTICOAGULANTS, *BIOTECHNOLOGY, *PHARMACEUTICAL industry, *TISSUES
Abstract

The purification of heparin from offal is an old industrial process for which commercial recipes date back to 1922. Although chemical, chemoenzymatic, and biotechnological alternatives for this production method have been published in the academic literature, animal-tissue is still the sole source for commercial heparin production in industry. Heparin purification methods are closely guarded industrial secrets which are not available to the general (scientific) public. However by reviewing the academic and patent literature, we aim to provide a comprehensive overview of the general methods used in industry for the extraction of heparin from animal tissue. [ABSTRACT FROM AUTHOR]

Published
2017
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28. Dose—response relationships of the tumorigenicity of cyclopenta[cd]pyrene, benzo [a]pyrene and 6-nitrochrysene in a newborn mouse lung adenoma bioassay.

Author

Busby, William F., Stevens, Ellen K., Kellenbach, Edwin R., Cornelisse, Jan, and Lugtenburg, Johan

Abstract

Cyclopenta[]pyrene (CPP) was a potent tumorigen when tested over a 5-fold dose range in the newborn mouse assay. A 20-fold increase in lung tumor multiplicity and a nearly 8-fold increase in tumor incidence was observed at the lowest total dose tested (1.55 μmol) with the dose-response relationship indicating a saturation of tumor multiplicity at ∼ 7 tumors/animal. No liver nodules or lymphatic system tumors were noted. Analysis of dose-response data for benzo [] pyrene (BaP) and 6-nitrochrysene (6-NC) showed that tumor multiplicity for BaP also saturated at ∼ 7 tumors/animal, whereas no similar saturation was found for 6-NC at up to 40 tumors/animal. Progression of lung adenomas to adenocarcinomas, as measured by the incidence of mice bearing malignant tumors, was essentially a linear function of dose. To facilitate comparison and maximize quantitative data obtainable from the newborn mouse assay-parameters were defined for tumor incidence (ED), tumor multiplicity (TM) and tumor malignancy (malignancy index). Values for the ED and TM were similar for the same compound and a tumorigenic potency series of 6-NC > BaP > CPP was obtained corresponding to a ratio of ∼1:10–25:76.5–135, respectively. The malignancy index, however, indicated increased adenocarcinoma induction in the order CPP > 6-NC > BaP as expressed by the ratio 1:1.4:8.3, respectively. [ABSTRACT FROM PUBLISHER]

Published
1988

29. Assignment of the <SUP>1</SUP>H and <SUP>13</SUP>C NMR spectra, sequence and conformation of the synthetic pentasaccharide SanOrg34006 and its precursors

Author

Bootsma, Judica, Wagenaars, Gerard, Dreef, Erik, Hout, Floris, and Kellenbach, Edwin

Abstract

Proton and carbon chemical shift data and proton–proton coupling constants of the synthetic antithrombotic pentasaccharide SanOrg34006 and its synthetic precursors are reported. Long-range heteronuclear correlation experiments allow the determination of the substitution pattern of the protecting groups in the precursor molecules. Also, the sequence of the oligosaccharide was confirmed this way. The conformation of the α-L-iduronic acid moiety was studied by the analysis of the 3J(1H,1H) coupling constants. Copyright © 2001 John Wiley & Sons, Ltd.

Published
2001

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