A derivative of uracil and precursor to riboflavin
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5-Amino-6-(D-ribitylamino)uracil (hydrochloride)

Item No. 39898

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1-[(5-amino-1,2,3,6-tetrahydro-2,6-dioxo-4-pyrimidinyl)amino]-1-deoxy-D-ribitol, monohydrochloride
CAS Number
134452-11-2
Synonyms
  • 5-Amino-6-ribitylamino-2,4(1H,3H)-Pyrimidinedione
  • 5-Amino-ribityl-Uracil
  • 5-A-RU
Molecular Formula
C9H16N4O6 • HCl
Formula Weight
312.7
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Acetonitrile: Slightly solubleWater: Soluble
SMILES
O=C(C(N)=C(NC[C@H](O)[C@H](O)[C@H](O)CO)N1)NC1=O
InChi Code
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
InChi Key
XKQZIXVJVUPORE-RPDRRWSUSA-N
Shipping & Storage Information
Storage
-80°C
Shipping
Dry ice in continental US; may vary elsewhere
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    500 µg

    $129

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    1 mg

    $245

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    5 mg

    $710

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    Product Description

    5-Amino-6-(D-ribitylamino)uracil (5-A-RU) is a derivative of uracil (Item No. 26088) and a precursor to riboflavin.1,2 It reacts non-enzymatically with dihydroxy acetone, methylglyoxal, or glyoxal to activate mucosal-associated invariant T (MAIT) cells isolated from iVα19-Tg and iVα19Vβ6-DTg mice.2 5-A-RU (100 nmol/animal, i.p.), when administered in combination with methylglyoxal, activates MAIT cells in iVα19 Cα-/--Tg mice. It is also a substrate for F0 synthase, an enzyme involved in the biosynthesis of the energy metabolism cofactor F420 in archaea, bacteria, and eukaryotes.1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Decamps, L., Philmus, B., Benjdia, A., et al. Biosynthesis of F0, precursor of the F420 cofactor, requires a unique two radical-SAM domain enzyme and tyrosine as substrate. J. Am. Chem. Soc. 134(44), 18173-18176 (2012).

    2. Soudais, C., Samassa, F., Sarkis, M., et al. In vitro and in vivo analysis of the gram-negative bacteria-derived riboflavin precursor derivatives activating mouse MAIT cells. J. Immunol. 194(10), 4641-4649 (2015).