DNAmod: 5-amino-6-(D-ribitylamino)uracil

Description

An aminouracil that is D-ribitol in which the hydroxy group at position 1 is substituted by the 6-amino group of 5,6-diaminouracil. Early intermediate in bacterial riboflavin synthesis.

Chemical properties

Chemical formula	Net charge	Average mass
C9H16N4O6, C9H16N4O6	0	276.24650

Nomenclature

IUPAC	SMILES	InChI	InChIKey	Synonyms
1-[(5-amino-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)amino]-1-deoxy-D-ribitol	Nc1c(NC[C@H](O)[C@H](O)[C@H](O)CO)[nH]c(=O)[nH]c1=O	InChI=1S/C9H16N4O6/c10-5-7(12-9(19)13-8(5)18)11-1-3(15)6(17)4(16)2-14/h3-4,6,14-17H,1-2,10H2,(H3,11,12,13,18,19)/t3-,4+,6-/m0/s1	XKQZIXVJVUPORE-RPDRRWSUSA-N	5-amino-6-ribitylamino-2,4-(1h,3h)pyrimidinedione 5-amino-6-(1-d-ribitylamino)uracil 6-(1-d-ribitylamino)-5-aminouracil 4-(1-d-ribitylamino)-5-amino-2,6-dihydroxypyrimidine 5-amino-2,6-dioxo-4-ribitylaminopyrimidine 5-a-ru 5-amino-6-(d-ribitylamino)uracil 6-(1-d-ribitylamino)-5-amino-2,4-dihydroxypyrimidine 5-arpd 5-amino-6-ribitylaminouracil

Database references:

CHEBI:15934

Citations

Bacher, A, et al. 1997. Biosynthesis of riboflavin: lumazine synthase and riboflavin synthase. Methods in Enzymology. 280.
Corbett, AJ, et al. 2014. T-cell activation by transitory neo-antigens derived from distinct microbial pathways. Nature. 509(7500).
Decamps, L, et al. 2012. Biosynthesis of F0, precursor of the F420 cofactor, requires a unique two radical-SAM domain enzyme and tyrosine as substrate. Journal of the American Chemical Society. 134(44).
Morgunova, E, et al. 2005. Crystal structure of lumazine synthase from Mycobacterium tuberculosis as a target for rational drug design: binding mode of a new class of purinetrione inhibitors. Biochemistry. 44(8).
Zhang, X, et al. 2001. X-ray structure analysis and crystallographic refinement of lumazine synthase from the hyperthermophile Aquifex aeolicus at 1.6 A resolution: determinants of thermostability revealed from structural comparisons. Journal of Molecular Biology. 306(5).