Uracil-4-carboxylic acid

The most interesting and important member of this series is orotic acid or uracil 6-carboxylic acid, (I). This compound was synthesized in 1897 by the condensa-... 

A common intermediate for all the nucleotides is 5-phosphoribosyl-l-diphosphate (PRPP), produced by successive ATP-dependent phosphorylations of ribose. This has an a-diphosphate leaving group that can be displaced in Sn2 reactions. Similar Sn2 reactions have been seen in glycoside synthesis (see Section 12.4) and biosynthesis (see Box 12.4), and for the synthesis of aminosugars (see Section 12.9). For pyrimidine nucleotide biosynthesis, the nucleophile is the 1-nitrogen of uracil-6-carboxylic acid, usually called orotic acid. The product is the nucleotide orotidylic acid, which is subsequently decarboxylated to the now recognizable uridylic acid (UMP). 

Orotic acid (uracil-6-carboxylic acid), first isolated147 from milk, has been amply demonstrated to be an effective precursor of nucleic acid and nu-... 

When treated with sodium metaperiodate, the barium salt of orotidine consumes one mole of oxidant per mole without the liberation of formic acid, in accord with a pentofuranosyl structure.119 The structure of orotidine, therefore, is certainly l-(D-ribofuranosyl)uracil-6-carboxylic acid (XXXII). 

Of 2,4-dialkoxypyrimidines, only 2,4di-tert-butoxy pyrimidine19 and 5-nitro-2,4-dimethoxypyrimidine20 failed to react in the normal Hilbert-Johnson fashion, and anomalous O-2-glycosyl derivatives have been obtained21 with a 2,4-dialkoxypyrimidine substituted in position 6, namely, with 2,4-diethoxy-6-meth3dpyrimidine anomeric 2-tetra-0-acetyl-D-glucopyranosyloxy-4-ethoxy-6-methylpyrimidines (18) resulted. Unsuccessful attempts to synthesize an X-l-ribo-furanosyl derivative of orotic acid (uracil-6 carboxylic acid) have been reported.22... 

UR 12592 rupatadine. uracil-6-carboxylic acid oroticadd. uracil mustard uramustine. uralenic acid enoxolone. 

Orotic Acid. l,2,3,6.Tetrahydro-2,6-dioxo-4-py-nmidinecartroxyhc acid uracil-6-carboxylic acid whey factor animal galactose factor Oropur Orotyl. CjH.N.O, mol wt 156.10. C 38.47%. H 2.58%, N 17.95%. O 41.00%. A pyrimidine precursor in animal organisms, found in milk Bachstez. Ber. 64, 2683 (1931) Hilbert, J. Am. Chem. Soc. 54, 2082 (1932) Johnson, Schroeder, ibid. 2942. Synthesis from aspartic acid Nye. Mitchell, ibid. 69, 1382 (1947). Prepn by condensation of urea with monoethyl ester of ox -alacetic acid in methanol Scriabine, U.S. pat. 2,937,175... 

Orotic acid Uracil-6-carboxylic acid C5HAO. 156.10 2.4 9.5 >13 0.18 (18°C)... 

Uracil-6-carboxylic acid (orotic acid) (C H O N ) (Values on Vol.3,... 

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