A<sup>13</sup>C NMR study of poly(adenosine diphosphate ribose) and its monomers: evidence of α-(1″→2′) ribofuranosyl ribofuranoside residue

Misawa, Miwa; Saitô, Hazime; Sakura, Harutake; Saikawa, Noriko; Watanabe, Fumiko; Matsushima, Taijiro; Sügimura, Takashi

doi:10.1093/nar/4.11.3997

Cited by 53 publications

(41 citation statements)

References 20 publications

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“…This may be of some significance in regard § Natural abundance carbon-13 spectra of PR-AMP derived from calf thymus nuclei also indicate a single, homogeneous product. The glycosyl linkage may also be a (27). Conformational rigidity extends into the a-ribose moiety, as indicated by its exclusively 1'-exo type conformation.…”

Section: Discussionmentioning

confidence: 99%

Structure of a poly (adenosine diphosphoribose) monomer: 2'-(5"-hosphoribosyl)-5'-adenosine monophosphate.

Ferro¹,

Oppenheimer²

1978

Proc. Natl. Acad. Sci. U.S.A.

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A preparation of poly(adenosine diphosphoribose) synthase obtained from pigeon liver nuclei has been used to make poly(adenosine diphosphoribose) with an average chain length of 20. Digestion of the purified poly(adenosine diphosphoribose) with snake venom phosphodiesterase (oligonucleate 5'-nucleotidohydrolase; EC 3.1.4.1) gave the monomer, 2'-5"-phosphoribosyl-5'-AMP. After purification of the monomer on a Dowex-1 column, further digestion with alkaline phosphatase [orthophosphoric-monoester phosphohydrolase (alkaline optimum); EC 3.1.3.1] yielded the dephosphorylated product, 2'-ribosyl adenosine. Nuclear magnetic resonance spectra at 360MHz of the 2'-ribosyl adenosine were obtained in [2H6Jdi-methylsulfoxide, which allows direct observation of the hydroxyl protons. These spectra show the absence of the adenosine 2'-hydroxyl proton, thus confirming the 2' position as the site of attachment of the ribose to the adenosine moiety. Comparison of the coupling constants and the chemical shifts of the ribose hydroxyl protons of 2'-ribosyl adenosine with the model compounds a-and fl-methylribofuranoside establishes an a (1" 2') glycosidic linkage in the monomer. No evidence was found for heterogeneity in either the site of attachment or configuration of the linkage in the 2'(5"-phosphoribosyl)5'-AMP. The nuclei of eukaryotic cells contain an enzyme that converts NAD+ into a homopolymer of repeating adenosine diphosphoribose (ADP-Rib) units with a concomitant release of nicotinamide (1-3). The poly(ADP-Rib) formed has a variable chain length and is covalently attached to histones and other nuclear proteins (4, 5). Although poly(ADP-Rib) has been shown to occur in vivo (5), its specific biological function is as yet undetermined, however there is possible evidence for its implication in DNA replication (5).Doly and Petek (6) exists that poly(ADP-Rib) may be heterogeneous with regard to the site of attachment of the ribosyl moiety. Further heterogeneity is possible since the anomeric configuration at R1" is unknown, although a fi configuration has been drawn (1, 5, 7). The implications arising from possible heterogeneity makes a structural determination imperative.Two classes of enzymes are known that can degrade poly(ADP-Rib): poly(ADP-Rib) glycohydrolases, which attack the ribosyl-adenosine bond (8, 9) liberating ADP-Rib, and pyrophosphatases, such as endogenous pyrophosphatases (10, 11) or snake venom phosphodiesterase (oligonucleate 5'-nucleotidohydrolase; EC 3.1.4.1) (12), which cleave the pyrophosphate linkage. The resulting monomer from the latter reactions, 2'-(5"-phosphoribosyl)-5'-AMP [AMP(P-Rib)], retains the glycosidic linkage and thus allows structural analysis. We report the 360 MHz 1H nuclear magnetic resonance (NMR) spectra of AMP(P-Rib) and 2'-ribosyladenosine (Rib-Ado). The analysis of these spectra allow6 the determination of both the site and configuration of the glycosidic linkage for poly(ADP-Rib) synthesized in uitro and provides evidence for the homogeneity of poly(ADP-Rib).MATERIALS AND...

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Section: Discussionmentioning

confidence: 99%

Structure of a poly (adenosine diphosphoribose) monomer: 2'-(5"-hosphoribosyl)-5'-adenosine monophosphate.

Ferro¹,

Oppenheimer²

1978

Proc. Natl. Acad. Sci. U.S.A.

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“…3 shows a 13 C NMR spectrum of G-ADP. Signals corresponding to the five carbons of the adenine moiety and to the five carbons of ribose were readily identified by comparison with the spectra of other adenine-containing nucleotides (22,26). Additionally, a signal at a position expected for the carbonyl carbon of a carboxylate group (179.98 ppm) and at a position expected for a carbon of a methylene group linked to a pyrophosphate bridge (71.18 ppm) could be identified.…”

Section: Identification Of Products Derived From Adp-ribose Glycation-mentioning

confidence: 98%

Glycation and Glycoxidation of Histones by ADP-ribose

Cervantes-Laurean¹,

Jacobson

1996

Journal of Biological Chemistry

121

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The reaction of long lived proteins with reducing sugars has been implicated in the pathophysiology of aging and age-related diseases. A likely intranuclear source of reducing sugar is ADP-ribose, which is generated following DNA damage from the turnover of ADP-ribose polymers. In this study, ADP-ribose has been shown to be a potent histone glycation and glycoxidation agent in vitro. Incubation of ADP-ribose with histones H1, H2A, H2B, and H4 at pH 7.5 resulted in the formation of ketoamine glycation conjugates. Incubation of histone H1 with ADP-ribose also rapidly resulted in the formation of protein carboxymethyllysine residues, protein-protein cross-links, and highly fluorescent products with properties similar to the advanced glycosylation end product pentosidine. The formation of glycoxidation products was related to the degradation of ketoamine glycation conjugates by two different pathways. One pathway resulted in the formation of protein carboxymethyllysine residues and release of an ADP moiety containing a glyceric acid fragment. A second pathway resulted in the release of ADP, and it is postulated that this pathway is involved in the formation of histone-histone cross-links and fluorescent advanced glycosylation end products.

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“…The pH of the hydrolyzate was adjusted to about 5 with barium hydroxide and centrifuged. The resulting supernatant was adjusted to pH 13 with 0.1 N NaOH and lyophilized. The lyophilizate was washed with 2 ml of ethanol twice, dissolved in 0.5 ml of water, and charged onto a column of Sephadex G-I0 (Pharmacia, 105 ml) previously equilibrated with 0.1 M NaC!.…”

Section: Methodsmentioning

confidence: 99%

The Structure of Ribocitrin and its Structure-activity Relationship in the Inhibition of Dextransucrase ofStreptococcus mutansE49

Takashio¹,

Ohnuki²,

Okami³

1982

Agricultural and Biological Chemistry

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A¹³C NMR study of poly(adenosine diphosphate ribose) and its monomers: evidence of α-(1″→2′) ribofuranosyl ribofuranoside residue

Cited by 53 publications

References 20 publications

Structure of a poly (adenosine diphosphoribose) monomer: 2'-(5"-hosphoribosyl)-5'-adenosine monophosphate.

Structure of a poly (adenosine diphosphoribose) monomer: 2'-(5"-hosphoribosyl)-5'-adenosine monophosphate.

Glycation and Glycoxidation of Histones by ADP-ribose

The Structure of Ribocitrin and its Structure-activity Relationship in the Inhibition of Dextransucrase ofStreptococcus mutansE49

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A13C NMR study of poly(adenosine diphosphate ribose) and its monomers: evidence of α-(1″→2′) ribofuranosyl ribofuranoside residue

Cited by 53 publications

References 20 publications

Structure of a poly (adenosine diphosphoribose) monomer: 2'-(5"-hosphoribosyl)-5'-adenosine monophosphate.

Structure of a poly (adenosine diphosphoribose) monomer: 2'-(5"-hosphoribosyl)-5'-adenosine monophosphate.

Glycation and Glycoxidation of Histones by ADP-ribose

The Structure of Ribocitrin and its Structure-activity Relationship in the Inhibition of Dextransucrase ofStreptococcus mutansE49

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A¹³C NMR study of poly(adenosine diphosphate ribose) and its monomers: evidence of α-(1″→2′) ribofuranosyl ribofuranoside residue