GM1 ganglioside containing a hydroxylated fatty acid moiety, GM1(OH), was synthesized starting from lyso-GM1 and D-(+)-2-hydroxystearic acid. The aggregative, geometrical and distribution properties of GM1(OH) were compared with those of stearic acid containing GM1 ganglioside; laser light scattering measurements, differential scanning calorimetry and fluorescence spectroscopy were used. GM1 and GM1(OH) are present in solution as micelles with a hydrodynamic radius of 58.7 and 60.0 Angstrom, and molecular mass of 470 and 570 kDa, respectively. The surface area occupied by the monomer of GM1(OH) at the lipid-water interface of the aggregate was calculated to be 117 Angstrom(2), which is 3 Angstrom(2) lower than that determined for GM1. Proton NMR analyses of GM1 and GM1(OH) suggest different three-dimensional structures at the ganglioside lipid-water interface. Both GM1(OH) and GM1 inserted into dipalmitoylphosphatidylcholine (DPPC) vesicles undergo segregation phenomena, with the formation of ganglioside-enriched microdomains, but GM1(OH) shows a higher degree of dispersion in the DPPC matrix and exerts a lower rigidifying effect than does GM1.

SYNTHESIS AND AGGREGATIVE PROPERTIES OF GM1 GANGLIOSIDE (IV(3)NEU5ACGGOSE(4)CER) CONTAINING D-(+)-2-HYDROXYSTEARIC ACID / S. SONNINO, D. ACQUOTTI, L. CANTU, V. CHIGORNO, M. VALSECCHI, R. CASELLATO, M. MASSERINI, M. CORTI, P. ALLEVI, G. TETTAMANTI. - In: CHEMISTRY AND PHYSICS OF LIPIDS. - ISSN 0009-3084. - 69:2(1994), pp. 95-104.

SYNTHESIS AND AGGREGATIVE PROPERTIES OF GM1 GANGLIOSIDE (IV(3)NEU5ACGGOSE(4)CER) CONTAINING D-(+)-2-HYDROXYSTEARIC ACID

S. SONNINO
Primo
;
L. CANTU;V. CHIGORNO;M. VALSECCHI;R. CASELLATO;M. CORTI;P. ALLEVI
Penultimo
;
G. TETTAMANTI
Ultimo
1994

Abstract

GM1 ganglioside containing a hydroxylated fatty acid moiety, GM1(OH), was synthesized starting from lyso-GM1 and D-(+)-2-hydroxystearic acid. The aggregative, geometrical and distribution properties of GM1(OH) were compared with those of stearic acid containing GM1 ganglioside; laser light scattering measurements, differential scanning calorimetry and fluorescence spectroscopy were used. GM1 and GM1(OH) are present in solution as micelles with a hydrodynamic radius of 58.7 and 60.0 Angstrom, and molecular mass of 470 and 570 kDa, respectively. The surface area occupied by the monomer of GM1(OH) at the lipid-water interface of the aggregate was calculated to be 117 Angstrom(2), which is 3 Angstrom(2) lower than that determined for GM1. Proton NMR analyses of GM1 and GM1(OH) suggest different three-dimensional structures at the ganglioside lipid-water interface. Both GM1(OH) and GM1 inserted into dipalmitoylphosphatidylcholine (DPPC) vesicles undergo segregation phenomena, with the formation of ganglioside-enriched microdomains, but GM1(OH) shows a higher degree of dispersion in the DPPC matrix and exerts a lower rigidifying effect than does GM1.
Settore BIO/10 - Biochimica
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/187159
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