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 Scopus citations

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 - Nov 1985
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology

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