5-A-RU-PABC-Val-Cit-Fmoc

• CAT Number: I045765
• CAS Number: 2677841-58-4
• Molecular Formula: C43H53N9O13
• Molecular Weight: 903.93
• Purity: ≥95%
• Synonyms: 9H-fluoren-9-ylmethyl N-[(2S)-1-[[(2S)-5-(carbamoylamino)-1-[4-[[2,4-dioxo-6-[[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]amino]-1H-pyrimidin-5-yl]carbamoyloxymethyl]anilino]-1-oxopentan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]carbamate
• InChI: InChI=1S/C43H53N9O13/c1-22(2)33(49-42(62)65-21-29-27-10-5-3-8-25(27)26-9-4-6-11-28(26)29)38(58)48-30(12-7-17-45-40(44)60)37(57)47-24-15-13-23(14-16-24)20-64-43(63)50-34-36(51-41(61)52-39(34)59)46-18-31(54)35(56)32(55)19-53/h3-6,8-11,13-16,22,29-33,35,53-56H,7,12,17-21H2,1-2H3,(H,47,57)(H,48,58)(H,49,62)(H,50,63)(H3,44,45,60)(H3,46,51,52,59,61)/t30-,31-,32+,33-,35-/m0/s1
• InChIKey: HGSKBBAITCBDNC-FAEFUHMUSA-N
• SMILES: CC(C)C(C(=O)NC(CCCNC(=O)N)C(=O)NC1=CC=C(C=C1)COC(=O)NC2=C(NC(=O)NC2=O)NCC(C(C(CO)O)O)O)NC(=O)OCC3C4=CC=CC=C4C5=CC=CC=C35

5-A-RU-PABC-Val-Cit-Fmoc is the proagent of 5-A-RU[1]. 5-A-RU, a precursor of bacterial Riboflavin, is a mucosal-associated invariant T (MAIT) cells activator. 5-A-RU forms potent MAIT-activating antigens via non-enzymatic reactions with small molecules, such as glyoxal and methylglyoxal, which are derived from other metabolic pathways[2][3][4].
When added to MAIT cell cultures, 5-A-RU-PABC-Val-Cit-Fmoc (Compound 10) induces higher levels of mucosal-associated invariant T (MAIT) cell activation than 5-A-RU alone[1].

Reference

[1]. Joshua Lange, et al. The Chemical Synthesis, Stability, and Activity of MAIT Cell Prodrug Agonists That Access MR1 in Recycling Endosomes. ACS Chem Biol. 2020 Feb 21;15(2):437-445.
 [Content Brief]

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

[3]. Eckle SB, et al. Recognition of Vitamin B Precursors and Byproducts by Mucosal Associated Invariant T Cells. J Biol Chem. 2015 Dec 18;290(51):30204-11.
 [Content Brief]

[4]. 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.
 [Content Brief]