Ureidopropionic acid

Sparidans RW, Bosch TM, Jorger M et al. Liquid chromatography-tandem mass spectrometric assay for the analysis of uracif 5,6-dihydrouracil and beta-ureidopropionic acid in urine for the mesurement of the aetivities of the pyrimidine catabolic etaymes. J Chromatogr B Analyt Technol BiomedLife Sci 2006 839 45-53. 

The above directions are based upon the methods of Hoogewerff and Van Doip, as modified by Holm and by Hale and Honan. -Alanine has also been prepared by the action of h3q)obromite upon succinimide and hydrolysis of the resulting /3-ureidopropionic acid by the action of ammonia upon /3-iodo-propionic acid by the hydrolysis of methyl carbomethoxy-/8-aminopropionate, obtained by the action of sodiiun methoxide on succinbromimide by the reduction of 3-nitrosopropionic acid by heating ethyl acrylate with alcoholic ammonia from succinyl-glycine ester by the azide synthesis and by the action of liquid ammonia upon methyl acrylate. ... 

Figure 1.30 Catabolic pathway of capecitabine from 19F NMR analysis of patients urine. All the compounds are represented in neutral form. CAP, capecitabine 5 dFCR, 5 -deoxy-5-fluorocytidine FC, 5-fluorocytosine OHFC, hydroxy-5-fluorocytosine 5 dFUR, 5 -deoxy-5-fluorouridine FU, 5-fluorouracil FUH2/ 5,6-dihydro-5-fluorouracil FUPA, a-fluoro-fi-ureidopropionic acid FBAL, u-fluoro-fi-alanine I, fluoride ion FHPA, 2-fluoro-3-hydroxypropanoic acid FAC, fluoroacetic acid. Metabolites identified for the first time in urine of patients with 19F NMR are represented in ellipses.

Dihydrouracil + H20 <=> / -Ureidopropionic Acid (catalyzed by Hydropyrimidine Hydratase)... 

Pathways for pyrimidine catabolism are shown in Figure 22.11. Pyrimidine bases are broken down through a common uracil intermediate, which is subsequently converted to dihydrouracil, followed by / -ureidopropionic acid, and finally / -alanine, ammonia and C02. ... 

Ureidopropionase is an enzyme in pyrimidine catabolism that catalyzes the reaction that follows / -Ureidopropionic acid + H2O <=> Alanine + NH4+ + CO2... 

Trifluoropentanoic acid 3-Ureidopropionic acid 3-(2-Nitropbenyl)pFopionic acid i/ a/ij-2-Metbylcinnamic acid... 

Fluorouracil is catabolized in an analogous manner to uracil, forming the following degradative products dihydrofluorouraci1, a-fluoro-6-ureidopropionic acid, a-fluoro-3-guanidopropionic acid, a-fluoro-3-alanine, urea, and CO2 (16). 

Albizziin (L-a-amino-/8-ureidopropionic acid, LXXVII), which accompanies willardiine in the seeds [420] bears a formal resemblance to willardiine. These two amino acids may well be biogenetically related. 

Anisomyces odoratus has been reported to produce odoriferous simple aromatic compounds, terpenes and lanostadienoic acids (22). The unusual amino acid 2-amino-4-N-ureidopropionic acid and its oxalyl derivative were recently isolated from Coniophora puteana (23). 

Evans, C.S., P.J. Burns, M. Dutton, S.Brown 2-Amino-4-N-ureidopropionic acid (albizzine) and its oxalyl derivative in hyphae of Coniophora puteana. Phytochem. 29, 2159 (1990). 

In this chapter, quisqualic acid, isolated from the fruits of Quisqualis indica, is described. Quisqualic acid is biosynthesized from 2,3-diaminopropionic acid. On the other hand, it can be said that quisqualic acid is biosynthesized from 2-amino-3-ureidopropionic acid, which is a derivative of 2,3-diaminopropionic acid. The former amino acid (2-amino-3-ureidopropionic acid) was isolated from the seeds of the silk tree Albizzia julibrissin) (Fabaceae) and was named albizziin. 

Regarding the biosynthesis of quisqualic acid, it is considered that 2,3-diaminopropionic acid or 2-amino-3-ureidopropionic acid, a derivative of the former amino acid, is a precursor. The latter amino acid structure was attributed to albizziin (2-amino-3-ureidopropionic acid or 3-((aminocarbonyl)-amino-L-alanine)), which was isolated from the seeds of the silk tree Albizzia julibrissiri) (Fabaceae) [9,10]. 

Carbamoyl phosphate HjN-COO PO3H2, an energy-rich phosphoiylated carbamate and an important metabolic intermediate. Carbamic acid, NHjCOOH, is unstable in fi ee form. Carbamate removed hydrolytically fi om carbamyl compounds, e.g. ureidopropionic acid (see Pyrimidine degradation), decomposes immediately into COj and NHj. Cp. is a specific precursor of arginine and urea (see Urea cycle), and of pyrimidines via orotic acid (see Pyrimidine biosynthesis). 

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