Acide 3-uréidoisobutyrique

Identification
Acide 3-uréidoisobutyrique

Structure de l'acide 3-uréidoisobutyrique
Nom UICPA	acide 3-(carbamoylamino)-2-méthylpropanoïque
Synonymes	acide β-uréidoisobutyrique
N^o CAS	2905-86-4 (RS)
N^o ECHA	100.236.960
ChEBI	1670
SMILES	CC(CNC(=O)N)C(=O)O PubChem, vue 3D
InChI	Std. InChI : vue 3D InChI=1S/C5H10N2O3/c1-3(4(8)9)2-7-5(6)10/h3H,2H2,1H3,(H,8,9)(H3,6,7,10) Std. InChIKey : PHENTZNALBMCQD-UHFFFAOYSA-N
Propriétés chimiques
Formule	C₅H₁₀N₂O₃ [Isomères]
Masse molaire^[1]	146,144 5 ± 0,006 g/mol C 41,09 %, H 6,9 %, N 19,17 %, O 32,84 %,

Unités du SI et CNTP, sauf indication contraire.
modifier

L’acide 3-uréidoisobutyrique, également appelé acide β-uréidoisobutyrique, est un intermédiaire métabolique de la dégradation de la thymine. Chez l'humain, elle s'accumule dans l'urine des patients souffrant d'un déficit en bêta-uréidopropionase^[2] (EC 3.5.1.6), ce qui permet de dépister les anomalies dans le métabolisme des pyrimidines et prévenir l'usage du 5-fluorouracile comme néoplasique lorsqu'il pourrait s'avérer gravement toxique pour l'organisme^[3].

Stéréochimie

L'acide 3-uréidoisobutyrique possède un atome de carbone asymétrique. Il est donc chiral et se présente sous la forme d'une paire d'énantiomères R et S.

Notes et références

↑ Masse molaire calculée d’après « Atomic weights of the elements 2007 », sur www.chem.qmul.ac.uk.
↑ (en) Morimasa Ohse, Masafumi Matsuo, Akihito Ishida et Tomiko Kuhara, « Screening and diagnosis of β-ureidopropionase deficiency by gas chromatographic/mass spectrometric analysis of urine », Journal of Mass Spectrometry, vol. 37, n^o 9,‎ septembre 2002, p. 954-962 (lire en ligne) DOI 10.1002/jms.354 PMID 12271438
↑ (en) Ute Hofmann, Matthias Schwab, Sonja Seefried, Claudia Marx, Ulrich M. Zanger, Michel Eichelbaum, Thomas E. Mürdter, « Sensitivemethod for the quantification of urinary pyrimidine metabolites in healthy adults by gas chromatography – tandem mass spectrometry », Journal of Chromatography B, vol. 791, n^os 1-2,‎ 5 juillet 2002, p. 371-380 (lire en ligne) DOI 10.1016/S1570-0232(03)00251-4 PMID 12798197

v · m

Intermédiaires du métabolisme des nucléotides

Purines

Anabolisme	R5P → IMP : PRPP PRA GAR FGAR FGAM AIR CAIR SAICAR AICAR FAICAR IMP → AMP : acide adénylosuccinique IMP → GMP : xanthosine monophosphate (XMP)
Catabolisme	hypoxanthine xanthine acide urique acide 5-hydroxyisourique

Pyrimidines

Anabolisme	carbamyl-phosphate acide uréidosuccinique acide 4,5-dihydroorotique acide orotique orotidine monophosphate (OMP) uridine monophosphate (UMP)
Catabolisme	uracile : 5,6-dihydrouracile N-Carbamyl-β-alanine β-alanine thymine : 5,6-dihydrothymine acide 3-uréidoisobutyrique acide 3-aminoisobutyrique

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