TY - JOUR
T1 - High-resolution proton NMR studies of gangliosides. III. elucidation of the structure of ganglioside GM3 lactone
AU - Yu, Robert K.
AU - Koerner, Theodore A.W.
AU - Ando, Susumu
AU - Yohe, Herbert C.
AU - Prestegard, James H.
PY - 1985/11
Y1 - 1985/11
N2 - Ganglioside GM3 lactone (1) was prepared in 95 % yield from the parent ganglioside by incubation at 25°C for 4 days in glacial acetic acid. Inspection of the 500 MHz proton NMR spectra of 1 and its precursor in dimethylsulfoxide-d6-deuterium oxide at 30°C revealed a large deshielding (+1.42 ppm) of the H-2 resonance of the galactosyl residue. This suggests that 1 must be the lactone formed by esterification of the sialic acid carboxyl group with the C-2 hydroxyl of the galactosyl residue. Consideration of all the NMR data leads to a specific structure proposal in which 1 has a highly rigid structure. Interesting features of the structure include a hydro phobic inner surface and a semicircular outer edge of seven-oxygen atoms, which may have physiological importance.
AB - Ganglioside GM3 lactone (1) was prepared in 95 % yield from the parent ganglioside by incubation at 25°C for 4 days in glacial acetic acid. Inspection of the 500 MHz proton NMR spectra of 1 and its precursor in dimethylsulfoxide-d6-deuterium oxide at 30°C revealed a large deshielding (+1.42 ppm) of the H-2 resonance of the galactosyl residue. This suggests that 1 must be the lactone formed by esterification of the sialic acid carboxyl group with the C-2 hydroxyl of the galactosyl residue. Consideration of all the NMR data leads to a specific structure proposal in which 1 has a highly rigid structure. Interesting features of the structure include a hydro phobic inner surface and a semicircular outer edge of seven-oxygen atoms, which may have physiological importance.
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U2 - 10.1093/oxfordjournals.jbchem.a135404
DO - 10.1093/oxfordjournals.jbchem.a135404
M3 - Article
C2 - 4086484
AN - SCOPUS:0022367040
SN - 0021-924X
VL - 98
SP - 1367
EP - 1373
JO - Journal of Biochemistry
JF - Journal of Biochemistry
IS - 5
ER -