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Glycobiology Advance Access published online on June 15, 2005
Glycobiology, doi:10.1093/glycob/cwi091
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© The Author 2005. Published by Oxford University Press. All rights reserved. For permissions, please e-mail: journals.permissions@oupjournals.org
Received March 29, 2005
Revised May 16, 2005
Accepted June 7, 2005

Article

Dynamic properties of biologically active synthetic heparin-like hexasaccharides

Jesús Angulo 1, Milos Hricovíni 2, Margarida Gairi 3, Marco Guerrini 4, José Luis de Paz 1, Rafael Ojeda 1, Manuel Martín-Lomas 5, and Pedro M. Nieto 1*

1 Grupo de Carbohidratos, Instituto de Investigaciones Químicas, CSIC. Américo Vespucio 49, Isla de la Cartuja, 41092 Sevilla. Spain
2 Institute of Chemistry, Slovak Academy of Sciences, 845 38 Bratislava, Slovakia
3 Unitat de RMN, Serveis Cientificotècnics, Universitat de Barcelona, Parc Científic de Barcelona, Josep Samitier, 1-5, 08028-Barcelona, Spain
4 Institute for Chemical and Biochemical Research "G. Ronzoni", via G. Colombo 81, 20133 Milan, Italy
5 Grupo de Carbohidratos, Instituto de Investigaciones Químicas, CSIC. Américo Vespucio 49, Isla de la Cartuja, 41092 Sevilla. Spain.

* To whom correspondence should be addressed.
Pedro M. Nieto, E-mail: pedro.nieto{at}iiq.csic.es


  Abstract

A complete study of the dynamics of two synthetic heparin-like hexasaccharides, D-GlcNHSO3-6-SO4-{alpha}-(1->4)-L-IdoA-2-SO4-{alpha}-(1->4)-D-GlcNHSO3-6-SO4-{alpha}-(1->4)-L-IdoA-2- SO4-{alpha}-(1->4)-D-GlcNHSO3-6-SO4-{alpha}-(1->4)-L-IdoA-2-SO4-{alpha}-1-> i Pr (1) and D-GlcNHSO3- {alpha}-(1->4)-L-IdoA-2-SO4-{alpha}-(1->4)-D-GlcNHAc-6-SO4-{alpha}-(1->4)-L-IdoA-{alpha}-(1->4)-D-GlcNHSO3-{alpha}-(1->4)-L-IdoA-2-SO4-{alpha}-1-> iPr (2), has been performed using 13C NMR relaxation parameters, T1, T2 and heteronuclear NOE’s. Compounds 1and 2are constituted from sequences corresponding to the major polysaccharide heparin region, differ from each other only in sulphation patterns, and are capable to stimulate FGF-1 induced mitogenesis. Both oligosaccharides exhibit a remarkable anisotropic overall motion in solution as revealed by their anisotropic ratios ({tau}{perp}/{tau}), 4.0 and 3.0 respectively. This is a characteristic behaviour of natural glycosaminoglycans which has also been observed for the antithrombin binding pentasaccharide D-GlcNHSO3-6-SO4-{alpha}-(1->4)-D-GlcA-{beta}-(1->4)-D-GlcNHSO3-(3,6-SO4)-{alpha}-(1->4)-L-IdoA-2-SO4-{alpha}-(1->4)-D-GlcNHSO3-6-SO4-{alpha}-1->Me 3 (Hricovíni et al.1995). The motional properties observed for 1and 2provide additional support to the suitability of these compounds as heparin models in agreement with previous structural (de Paz et al., 2001, Ojeda et al., 2002, Lucas et al., 2003) and biological data (Angulo, et al., 2004). Fast internal motions observed for the less sulphated compound 2, as compared with 1, may be related to their different behaviour in stimulating FGF1-induced mitogenic activity (Angulo, et al., 2004).

Keywords: Heparin/Heparan sulphate/NMR relaxation/anisotropy/FGF interaction/oligossacharides.
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