GLYCINE RIBOTIDE INTERMEDIATES IN THE de novo SYNTHESIS OF INOSINIC ACID<sup>1</sup>

Goldthwait, David A.; Peabody, Richard A.; Greenberg, Gordon R.

doi:10.1021/ja01649a102

Cited by 66 publications

(10 citation statements)

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“…on silica gel showed only a single spot, and microanalysis indicated the empirical formula of 4 (a or p form). We conclude, there- This compound (5) gave the same R, value (Table 1) as the authentic radioactive compound obtained from Ehrlich ascites tumor cells by the method of Henderson (14), and with values reported by others (15)(16)(17). On two chromatograms (solvents B and C) two zones were present, possibly due to the anomeric forms of compound 5 as noted by Westby and Gots (16) and Goldthwait et al (15).…”

Section: Resultssupporting

confidence: 84%

New chemical synthesis of 5′-phosphoribosyl-N-formylglycineamide

Chu¹,

Henderson²

1970

Can. J. Chem.

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A new and convenient synthetic route to forrnylglycineamide ribonucleotide, an intermediate in the pathway of purine ribonucleotide biosynthesis de novo, is described. The method utilizes direct phosphorylation of the 5'-position of the linear riboside without protection of the 2',3'-hydroxyl groups of the ribose, and gives a good yield of mixed u and 0 anomers. This route is suitable for synthesis of thenatural product in quantities required for biological studies.

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Section: Resultssupporting

confidence: 84%

New chemical synthesis of 5′-phosphoribosyl-N-formylglycineamide

Chu¹,

Henderson²

1970

Can. J. Chem.

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“…At least two factors do appear to have roles. First, the introduction of N15 into positions other than N-7 of the purine ring, because of transamination and entry of N15 into aspartic acid and the amide-N of glutamine, the precursors of N-1 and of N-3 and N-9, respectively (19)(20)(21), would tend to introduce a greater percentage of a given dose of glycine-N'5 into uric acid than of glycine-1-C"4, which appears to label C-4 quite specifically.…”

Section: Discussionmentioning

confidence: 99%

Overproduction of Uric Acid as the Cause of Hyperuricemia in Primary Gout

Wyngaarden¹

1957

J. Clin. Invest.

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Glycine contributes carbon atoms 4 and 5 and nitrogen atom 7 of the purine ring (1-3). Benedict, Yfi, Bien, Gutman and Stetten (4) have described experiments in which the abundance of N15 in uric acid was measured for several days following an oral test dose of glycine-N'5. In two gouty subjects, three times as much of the administered N15 was recovered in urinary uric acid as in normal subjects. In two others, however, normal quantities of N15 appeared in uric acid. In these studies, there was a rank order correlation between the daily excretion of uric acid in the urine and the per cent of ingested isotope appearing in urinary uric acid. In subjects who exhibited abnormally high basal uric acid excretions, an abnormally rapid and excessive incorporation of dietary glycine into uric acid occurred. In others whose basal excretion was approximately normal, utilization of glycine for uric acid synthesis was normal. Muller and Bauer (5) and Bishop, Rand, and Talbott (6) have each reported an additional gouty patient excreting normal quantities of uric acid who incorporated normal quantities of glycine-N'5 into urinary uric acid. The latter authors also described one gouty patient who incorporated excessive quantities of glycine-N'5 into urinary uric acid on two of three occasions despite a normal urinary urate excretion. These studies, therefore, demonstrated that overproduction of uric acid was present in some gouty subjects, but failed to give a clear indication of the cause of hyperuricemia in another, perhaps predominant group of the gouty population.Recently, we have administered glycine-1-C'4 to control and gouty patients in order to label urinary purines, as part of a study of intermediates in urate synthesis (7). The first two gouty patients both exhibited excessive incorporation of C14 into urinary urate, one despite a normal urate excretion (7,8). It was therefore decided to re-investigate the problem of the rate of generation of uric acid in gout, employing tracer doses of glycine-1-C"4 rather than large doses of glycine-N'5 as were required in previous studies.In the present study, glycine-1-C'4 was administered orally in 2.5 to 25 uc. doses to control and gouty subjects, and the concentration and cumulative incorporation of isotope into urinary uric acid were determined. This paper presents data indicating that overincorporation of glycine-1-C'4 into uric acid is a consistent finding in primary gout, and that the failure of the glycine-N'5 technique to disclose overincorporation in some gouty subjects may have been the result of the large dose of glycine employed. These results have been interpreted as showing that the hyperuricemia of primary gout is due to overproduction of uric acid in the majority if not all gouty subjects. METHODSGlycine-1-C'4, specific activity 1 to 2 mc. per mM, was purchased from Nuclear Instrument and Chemical Company. Uric acid determinations were performed by differential spectrophotometry according to Praetorius (9), employing purified uricase purchased from Worthington Bio...

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“…Eiweißreiche Kost erhöht diese endogene Harnsäurequote [54][55][56][57][58]. Durch Isotopenversuche, be sonders des Arbeitskreises von Buchanan [59][60][61][62][63] und anderen [64][65][66][67], wurde die H erkunft der einzelnen Atome des Harnsäureskelettes aufgeklärt: Die Aminosäure Glykokoll wird als Ganzes eingebaut (CAtom in Stellung 4 und 5, N-Atom in Stellung 7); dann kommen die drei N-Atome in Stellung 1, 3 und 9 aus dem allgemeinen «Amino säurepool» von Asparaginsäure und Säureamidgruppe des Glutamins und die drei noch fehlenden C-Atome (Stellung 2, 6 und 8) entstam men der Ameisen-und Kohlensäure. Dam it wäre also die Verknüp fung des Purinstoffwechsels m it dem Aminosäurestoffwechsel bewie sen und die einzelnen Schritte der Synthese sind auch genau bekannt [3].…”

Section: T Agung 204unclassified

Die Gicht

Schwarting¹

1962

Digestion

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GLYCINE RIBOTIDE INTERMEDIATES IN THE de novo SYNTHESIS OF INOSINIC ACID¹

Cited by 66 publications

References 1 publication

New chemical synthesis of 5′-phosphoribosyl-N-formylglycineamide

New chemical synthesis of 5′-phosphoribosyl-N-formylglycineamide

Overproduction of Uric Acid as the Cause of Hyperuricemia in Primary Gout

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GLYCINE RIBOTIDE INTERMEDIATES IN THE de novo SYNTHESIS OF INOSINIC ACID1

Cited by 66 publications

References 1 publication

New chemical synthesis of 5′-phosphoribosyl-N-formylglycineamide

New chemical synthesis of 5′-phosphoribosyl-N-formylglycineamide

Overproduction of Uric Acid as the Cause of Hyperuricemia in Primary Gout

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GLYCINE RIBOTIDE INTERMEDIATES IN THE de novo SYNTHESIS OF INOSINIC ACID¹