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 language | English |
|---|---|
| Pages (from-to) | 95-104 |
| Number of pages | 10 |
| Journal | Chemistry and Physics of Lipids |
| Volume | 69 |
| Issue number | 2 |
| DOIs | |
| Publication status | Published - 1994 |
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Keywords
- Ganglioside aggregates
- Gangliosides
- Hydroxy fatty acid
ASJC Scopus subject areas
- Biochemistry
- Biophysics
Cite this
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 journal › Article
}
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 -