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J. Biol. Chem., Vol. 255, Issue 22, 10710-10716, 11, 1980
BG Van Ness, JB Howard and JW Bodley
NMR spectral analysis of the novel amino acid, diphthamide, in elongation
factor 2 which is ADP-ribosylated by diphtheria toxin suggests that it is
2-[3-carboxyamido-3- (trimethylammonio)propyl]histidine.
Ribosyl-diphthamide was prepared by enzymatic hydrolysis of
ADP-ribosyl-elongation factor 2 and three compounds were produced by its
chemical hydrolysis (Van Ness, B. G., Howard, J. B., and Bodley, J. W.
(1980) J. Biol. Chem. 255, 10717- 10720). Proton NMR spectroscopy in 2H2O
of diphthine demonstrated the elements of histidine minus the carbon 2
proton plus 14 additional nonexchangeable protons. These protons were
attributed to an extensive modification at carbon 2 of the imidazole ring.
Proton NMR spectroscopy in 2H2O of ribosyl-diphthamide showed only those
protons seen in diphthine plus those expected of a ribofuranosylmoiety.
Chemical shift dependence on pH was demonstrated for the histidine-derived
protons as well as several protons of the modifying side chain. Natural
abundance carbon 13 NMR spectroscopy of ribosyldiphthamide also showed the
elements of histidine and ribose plus 7 additional carbon atoms attributed
to the modification of the imidazole ring. Based on the NMR spectral
properties of the anomeric proton of ribosyldiphthamide we propose that the
ribose is linked to one of the nitrogens of the histidine imidazole ring.
ADP-ribosylation of elongation factor 2 by diphtheria toxin. NMR spectra and proposed structures of ribosyl-diphthamide and its hydrolysis products
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