Analysis of the lipoteichoic-acid-like macroamphiphile from Bifidobacterium bifidum subspecies pennsylvanicum by one- and two-dimensional 1H- and 13C-NMR spectroscopy.

Abstract

The native lipoteichoic-acid-like amphiphile from Bifidobacterium bifidum subspecies pennsylvanicum and its basic glycan moiety, obtained by alkaline hydrolysis, were studied by 1H-, 13C-, and 31P-NMR, DEPT (distorsionless enhancement by polarization transfer), 1H-1H correlation spectroscopy and 13C-1H shift correlation NMR spectroscopy. The results are consistent with the structure elucidated by chemical analysis (Fischer, W., preceding paper in this journal): (formula; see text) and establish the structures of the repeating units independently. In addition to characteristic shifts in the 13C-NMR spectrum, the sites of phosphodiester and alanine ester bonds are also manifest in the 1H-NMR spectrum. Substitution of the glycerophosphate residues can be recognized in the 31P-NMR spectrum also.