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Kovensky, J.; Mallet, J.-M.; Esnault, J.; Driguez, P.-A.; Sizun, P.; Hérault, J.-P.; Herbert, J.-M.; Petitou, M.; Sinaÿ, P. "Further evidence for the critical role of a non-chair conformation of L-iduronic acid in the activation of antithrombin" (2002) European Journal of Organic Chemistry(21):3595-3603
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Abstract:

L-iduronic acid, a conformationally flexible monosaccharide, imparts a remarkable protein adaptability to the glycosaminoglycans heparin, heparan sulfate, and dermatan sulfate. The pentasaccharide representing the antithrombin binding site of heparin contains one such L-iduronic acid residue, the conformation of which has been suspected for a long time to be a critical factor in the interaction with antithrombin. We have recently synthesized pentasaccharides containing an L-iduronic acid residue conformationally forced to exist within a restricted arc (2S0 ⇄ 2,5B ⇄ 5S1) of the overall pseudorotational circle. We could thus demonstrate that the 2S0 conformation is adopted upon binding to the protein. In the present work, we now describe the synthesis of a similar pentasaccharide containing a slightly more flexible L-iduronic acid unit with a three-atom bridge between C-2 and C5 of the hexopyranose ring. This pentasaccharide is a better activator of AT-III with respect to blood coagulation factor Xa inhibition. These results confirm that L-iduronic acid adopts an unusual non-chair conformation close to 2S0 and clearly explains how the unique conformational behavior of L-iduronic acid is the key to heparin's interaction with AT-III. © Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

Registro:

Documento: Artículo
Título:Further evidence for the critical role of a non-chair conformation of L-iduronic acid in the activation of antithrombin
Autor:Kovensky, J.; Mallet, J.-M.; Esnault, J.; Driguez, P.-A.; Sizun, P.; Hérault, J.-P.; Herbert, J.-M.; Petitou, M.; Sinaÿ, P.
Filiación:Département de Chimie, Associé au CNRS, Ecole Normale Supérieure, 24, Rue Lhomond, 75231 Paris Cedex 05, France
Consejo Nacional de Investigaciones de la Republica Argentina (CONICET), Departamento de Química Orgánica, Ciudad Universitaria, 1428 Buenos Aires, Argentina
Département Cardiovasculaire/Thrombose, Sanofi-Synthélabo, 195, Route d'Espagne, 31036 Toulouse Cedex, France
DARA, Sanofi-Synthélabo, 371, Rue du Professeur Joseph Blayac, 34184 Montpellier Cedex, France
Palabras clave:Antithrombin; Carbohydrates; Glycosylation; Heparin; Iduronic acid; antithrombin; blood clotting factor 10a; dermatan sulfate; heparan sulfate; heparin; iduronic acid; pentasaccharide; article; binding affinity; binding kinetics; binding site; chemical structure; protein binding; protein conformation; protein interaction; structure analysis
Año:2002
Número:21
Página de inicio:3595
Página de fin:3603
DOI: http://dx.doi.org/10.1002/1099-0690(200211)2002:21<3595::AID-EJOC3595>3.0.CO;2-F
Título revista:European Journal of Organic Chemistry
Título revista abreviado:Eur. J. Org. Chem.
ISSN:1434193X
CODEN:EJOCF
CAS:antithrombin, 9000-94-6; blood clotting factor 10a, 72162-96-0, 9002-05-5; dermatan sulfate, 24967-94-0; heparan sulfate, 9050-30-0; heparin, 37187-54-5, 8057-48-5, 8065-01-8, 9005-48-5; iduronic acid, 3402-98-0
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_1434193X_v_n21_p3595_Kovensky

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Citas:

---------- APA ----------
Kovensky, J., Mallet, J.-M., Esnault, J., Driguez, P.-A., Sizun, P., Hérault, J.-P., Herbert, J.-M.,..., Sinaÿ, P. (2002) . Further evidence for the critical role of a non-chair conformation of L-iduronic acid in the activation of antithrombin. European Journal of Organic Chemistry(21), 3595-3603.
http://dx.doi.org/10.1002/1099-0690(200211)2002:21<3595::AID-EJOC3595>3.0.CO;2-F
---------- CHICAGO ----------
Kovensky, J., Mallet, J.-M., Esnault, J., Driguez, P.-A., Sizun, P., Hérault, J.-P., et al. "Further evidence for the critical role of a non-chair conformation of L-iduronic acid in the activation of antithrombin" . European Journal of Organic Chemistry, no. 21 (2002) : 3595-3603.
http://dx.doi.org/10.1002/1099-0690(200211)2002:21<3595::AID-EJOC3595>3.0.CO;2-F
---------- MLA ----------
Kovensky, J., Mallet, J.-M., Esnault, J., Driguez, P.-A., Sizun, P., Hérault, J.-P., et al. "Further evidence for the critical role of a non-chair conformation of L-iduronic acid in the activation of antithrombin" . European Journal of Organic Chemistry, no. 21, 2002, pp. 3595-3603.
http://dx.doi.org/10.1002/1099-0690(200211)2002:21<3595::AID-EJOC3595>3.0.CO;2-F
---------- VANCOUVER ----------
Kovensky, J., Mallet, J.-M., Esnault, J., Driguez, P.-A., Sizun, P., Hérault, J.-P., et al. Further evidence for the critical role of a non-chair conformation of L-iduronic acid in the activation of antithrombin. Eur. J. Org. Chem. 2002(21):3595-3603.
http://dx.doi.org/10.1002/1099-0690(200211)2002:21<3595::AID-EJOC3595>3.0.CO;2-F