title: Amino acid-specific ADP-ribosylation.
abstract: [adenine-U-14C]ADP-ribose-agmatine and [adenine-U-14C ))ADP-ribose-histone were synthesized by an NAD:arginine ADP-ribosyltransferase from [14C]NAD and agmatine and histone, respectively. The pseudo-first order rate constants for breakdown of the two components either in 0.4 N NaOH or in 0.4 M neutral hydroxylamine were identical. Hydroxylamine treatment of [14C]ADP-ribose-agmatine or [32P]ADP-ribose-histone yielded a single radioactive product which was separated by high pressure liquid chromatography and identified as ADP-ribose-hydroxamate by the formation of a ferric chloride complex. Hydrolysis of ADP-ribose-hydroxamate with snake venom phosphodiesterase resulted in the formation of 5'-AMP, consistent with the presence of a pyrophosphate bond. Incubation of ADP-ribose-[14C]agmatine, synthesized by the ADP-ribosyltransferase from NAD and [14C]agmatine, with 0.4 M neutral hydroxylamine resulted in the release of [14C]agmatine rather than phosphoribosyl[14C]agmatine. In addition, neither NAD nor ADP-ribose reacts with hydroxylamine; i.e. there was no evidence of nucleophilic attack by hydroxylamine at the pyrophosphate bond. The ADP-ribosyl-protein linkage formed by the NAD:arginine ADP-ribosyltransferase is considerably more stable to hydroxylamine than is the ADP-ribose-glutamate bond. The presence of ADP-ribose-arginine and ADP-ribose-glutamate synthesized by the ADP-ribosyltransferase and poly(ADP-ribose) synthetase, respectively, may be the chemical basis for the "hydroxylamine-stable" and "hydroxylamine-labile" bonds described by Hilz (Hilz, H. (1981) Hoppe-Seyler's Z. Physiol. Chem. 362, 1415-1425).
mesh_terms: D036002:ADP Ribose Transferases; D000246:Adenosine Diphosphate Ribose / Q000031:analogs & derivatives* / Q000378:metabolism; D000376:Agmatine / Q000378:metabolism; D000818:Animals; D011756:Diphosphates / Q000378:metabolism; D004355:Drug Stability; D006207:Half-Life; D006657:Histones / Q000378:metabolism; D006878:Hydroxides / Q000494:pharmacology*; D019811:Hydroxylamine; D006898:Hydroxylamines / Q000494:pharmacology*; D009702:Nucleoside Diphosphate Sugars; D010430:Pentosyltransferases / Q000378:metabolism*; D043264:Phosphodiesterase I; D010727:Phosphoric Diester Hydrolases / Q000378:metabolism; D011065:Poly(ADP-ribose) Polymerases; D014422:Turkeys
chemical_list: D011756:Diphosphates; D006657:Histones; D006878:Hydroxides; D006898:Hydroxylamines; D009702:Nucleoside Diphosphate Sugars; D000246:Adenosine Diphosphate Ribose; D019811:Hydroxylamine; D000376:Agmatine; C031356:hydroxide ion; D036002:ADP Ribose Transferases; D010430:Pentosyltransferases; D011065:Poly(ADP-ribose) Polymerases; D010727:Phosphoric Diester Hydrolases; D043264:Phosphodiesterase I; C470790:phosphodiesterase I, snake venom