High-resolution proton NMR studies of gangliosides. III. elucidation of the structure of ganglioside GM3 lactone

Robert K Yu, Theodore A.W. Koerner, Susumu Ando, Herbert C. Yohe, James H. Prestegard

Research output: Contribution to journalArticle

59 Citations (Scopus)

Abstract

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.

Original languageEnglish (US)
Pages (from-to)1367-1373
Number of pages7
JournalJournal of Biochemistry
Volume98
Issue number5
DOIs
StatePublished - Jan 1 1985
Externally publishedYes

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Deuterium Oxide
Gangliosides
Esterification
N-Acetylneuraminic Acid
Lactones
Dimethyl Sulfoxide
Acetic Acid
Hydroxyl Radical
Protons
Nuclear magnetic resonance
Oxygen
Rigid structures
Inspection
Atoms
ganglioside GM3 lactone

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology

Cite this

High-resolution proton NMR studies of gangliosides. III. elucidation of the structure of ganglioside GM3 lactone. / Yu, Robert K; Koerner, Theodore A.W.; Ando, Susumu; Yohe, Herbert C.; Prestegard, James H.

In: Journal of Biochemistry, Vol. 98, No. 5, 01.01.1985, p. 1367-1373.

Research output: Contribution to journalArticle

Yu, Robert K ; Koerner, Theodore A.W. ; Ando, Susumu ; Yohe, Herbert C. ; Prestegard, James H. / High-resolution proton NMR studies of gangliosides. III. elucidation of the structure of ganglioside GM3 lactone. In: Journal of Biochemistry. 1985 ; Vol. 98, No. 5. pp. 1367-1373.
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