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

Modify Date: 2024-01-02 19:59:51

5-amino-6-(D-ribitylamino)uracil Structure
5-amino-6-(D-ribitylamino)uracil structure
Common Name 5-amino-6-(D-ribitylamino)uracil
CAS Number 17014-74-3 Molecular Weight 276.24700
Density 1.7±0.1 g/cm3 Boiling Point N/A
Molecular Formula C9H16N4O6 Melting Point N/A
MSDS N/A Flash Point N/A

 Use of 5-amino-6-(D-ribitylamino)uracil


5-Amino-6-(D-ribitylamino)uracil (5-A-RU) is a precursor of bacterial Riboflavin. 5-Amino-6-(D-ribitylamino)uracil is a mucosal-associated invariant T (MAIT) cells activator. 5-Amino-6-(D-ribitylamino)uracil forms potent MAIT-activating antigens via non-enzymatic reactions with small molecules, such as glyoxal and methylglyoxal, which are derived from other metabolic pathways[1][2][3].

 Names

Name 5-amino-6-(D-ribitylamino)uracil
Synonym More Synonyms

 5-amino-6-(D-ribitylamino)uracil Biological Activity

Description 5-Amino-6-(D-ribitylamino)uracil (5-A-RU) is a precursor of bacterial Riboflavin. 5-Amino-6-(D-ribitylamino)uracil is a mucosal-associated invariant T (MAIT) cells activator. 5-Amino-6-(D-ribitylamino)uracil forms potent MAIT-activating antigens via non-enzymatic reactions with small molecules, such as glyoxal and methylglyoxal, which are derived from other metabolic pathways[1][2][3].
Related Catalog
In Vitro The MAIT antigens formed by the reactions between 5-Amino-6-(D-ribitylamino)uracil and glyoxal/methylglyoxal are simple adducts, 5-(2-oxoethylideneamino)-6-D-ribitylaminouracil (5-OE-RU) and 5-(2-oxopropylideneamino)-6-D-ribitylaminouracil (5-OP-RU), respectively, which bound to MR1 as shown by crystal structures of MAIT TCR ternary complexes[1]. 5-A-RU presents in diverse bacteria and yeast as well as plants. 5-A-RU plays an important role in MAIT cell activation, MR1 could not be refolded efficiently with 5-ARU alone. 5-A-RU is a precursor for MAIT cell ligand[2]. 5-A-RU can react extemporaneously with glyoxal and methylglyoxal to generate pyrimidine adducts that activate mouse MAIT cells from STg (iVa19) and DTg (iVa19Vb6) animals[3].
In Vivo 5-A-RU (100 nM; i.p.; 18 hours) and methylglyoxal (MeG) are mixed extemporaneously, MAIT cells are activated in iVa19 Cα-/- Tg mice (generated on the C57BL/6 background)[3].
References

[1]. Corbett AJ, et al. T-cell activation by transitory neo-antigens derived from distinct microbial pathways. Nature. 2014 May 15;509(7500):361-5.

[2]. Eckle SB, et al. Recognition of Vitamin B Precursors and Byproducts by Mucosal Associated Invariant T Cells.

[3]. Soudais C, et al. In Vitro and In Vivo Analysis of the Gram-Negative Bacteria-Derived Riboflavin PrecursorDerivatives Activating Mouse MAIT Cells. J Immunol. 2015 May 15;194(10):4641-9.

 Chemical & Physical Properties

Density 1.7±0.1 g/cm3
Molecular Formula C9H16N4O6
Molecular Weight 276.24700
Exact Mass 276.10700
PSA 184.69000
LogP -3.84
Index of Refraction 1.676

 Synonyms

1-[(5-Amino-2,6-dioxo-1,2,3,6-tetrahydro-4-pyrimidinyl)amino]-1-deoxy-D-ribitol
D-Ribitol, 1-[(5-amino-1,2,3,6-tetrahydro-2,6-dioxo-4-pyrimidinyl)amino]-1-deoxy-