Synthesis and aggregative properties of GM1 ganglioside (IV3Neu5AcGgOse4Cer) containing d-(+)-2-hydroxystearic acid

Sandro Sonnino, Domenico Acquotti, Laura Cantu', Vanna Chigorno, Manuela Valsecchi, Riccardo Casellato, Massimo Masserini, Mario Corti, Piero Allevi, Guido Tettamanti

Research output: Contribution to journalArticle

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 Å, 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 Å 2, which is 3 Å 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.

Original languageEnglish
Pages (from-to)95-104
Number of pages10
JournalChemistry and Physics of Lipids
Volume69
Issue number2
DOIs
Publication statusPublished - 1994

Fingerprint

G(M1) Ganglioside
1,2-Dipalmitoylphosphatidylcholine
Gangliosides
Lipids
Water
Fluorescence Spectrometry
Differential Scanning Calorimetry
Fluorescence spectroscopy
Molecular mass
Micelles
Hydrodynamics
Light scattering
Protons
Differential scanning calorimetry
Lasers
Fatty Acids
Monomers
Nuclear magnetic resonance
Light
2-hydroxystearic acid

Keywords

  • Ganglioside aggregates
  • Gangliosides
  • Hydroxy fatty acid

ASJC Scopus subject areas

  • Biochemistry
  • Biophysics

Cite this

Sonnino, S., Acquotti, D., Cantu', L., Chigorno, V., Valsecchi, M., Casellato, R., ... Tettamanti, G. (1994). Synthesis and aggregative properties of GM1 ganglioside (IV3Neu5AcGgOse4Cer) containing d-(+)-2-hydroxystearic acid. Chemistry and Physics of Lipids, 69(2), 95-104. https://doi.org/10.1016/0009-3084(94)90031-0

Synthesis and aggregative properties of GM1 ganglioside (IV3Neu5AcGgOse4Cer) containing d-(+)-2-hydroxystearic acid. / Sonnino, Sandro; Acquotti, Domenico; Cantu', Laura; Chigorno, Vanna; Valsecchi, Manuela; Casellato, Riccardo; Masserini, Massimo; Corti, Mario; Allevi, Piero; Tettamanti, Guido.

In: Chemistry and Physics of Lipids, Vol. 69, No. 2, 1994, p. 95-104.

Research output: Contribution to journalArticle

Sonnino, S, Acquotti, D, Cantu', L, Chigorno, V, Valsecchi, M, Casellato, R, Masserini, M, Corti, M, Allevi, P & Tettamanti, G 1994, 'Synthesis and aggregative properties of GM1 ganglioside (IV3Neu5AcGgOse4Cer) containing d-(+)-2-hydroxystearic acid', Chemistry and Physics of Lipids, vol. 69, no. 2, pp. 95-104. https://doi.org/10.1016/0009-3084(94)90031-0
Sonnino, Sandro ; Acquotti, Domenico ; Cantu', Laura ; Chigorno, Vanna ; Valsecchi, Manuela ; Casellato, Riccardo ; Masserini, Massimo ; Corti, Mario ; Allevi, Piero ; Tettamanti, Guido. / Synthesis and aggregative properties of GM1 ganglioside (IV3Neu5AcGgOse4Cer) containing d-(+)-2-hydroxystearic acid. In: Chemistry and Physics of Lipids. 1994 ; Vol. 69, No. 2. pp. 95-104.
@article{d666f937e277426896ccd9c3582b448c,
title = "Synthesis and aggregative properties of GM1 ganglioside (IV3Neu5AcGgOse4Cer) containing d-(+)-2-hydroxystearic acid",
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 {\AA}, 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 {\AA} 2, which is 3 {\AA} 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.",
keywords = "Ganglioside aggregates, Gangliosides, Hydroxy fatty acid",
author = "Sandro Sonnino and Domenico Acquotti and Laura Cantu' and Vanna Chigorno and Manuela Valsecchi and Riccardo Casellato and Massimo Masserini and Mario Corti and Piero Allevi and Guido Tettamanti",
year = "1994",
doi = "10.1016/0009-3084(94)90031-0",
language = "English",
volume = "69",
pages = "95--104",
journal = "Chemistry and Physics of Lipids",
issn = "0009-3084",
publisher = "Elsevier Ireland Ltd",
number = "2",

}

TY - JOUR

T1 - Synthesis and aggregative properties of GM1 ganglioside (IV3Neu5AcGgOse4Cer) containing d-(+)-2-hydroxystearic acid

AU - Sonnino, Sandro

AU - Acquotti, Domenico

AU - Cantu', Laura

AU - Chigorno, Vanna

AU - Valsecchi, Manuela

AU - Casellato, Riccardo

AU - Masserini, Massimo

AU - Corti, Mario

AU - Allevi, Piero

AU - Tettamanti, Guido

PY - 1994

Y1 - 1994

N2 - 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 Å, 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 Å 2, which is 3 Å 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.

AB - 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 Å, 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 Å 2, which is 3 Å 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.

KW - Ganglioside aggregates

KW - Gangliosides

KW - Hydroxy fatty acid

UR - http://www.scopus.com/inward/record.url?scp=0028204135&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0028204135&partnerID=8YFLogxK

U2 - 10.1016/0009-3084(94)90031-0

DO - 10.1016/0009-3084(94)90031-0

M3 - Article

C2 - 8181107

AN - SCOPUS:0028204135

VL - 69

SP - 95

EP - 104

JO - Chemistry and Physics of Lipids

JF - Chemistry and Physics of Lipids

SN - 0009-3084

IS - 2

ER -