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

5-A-RU-PABC-Val-Cit-Fmoc is the prodrug of 5-A-RU. 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.

Product information

Molecular Weight: 903.93

Formula: C43H53N9O13

Chemical Name: (9H-fluoren-9-yl)methyl N-[(1S)-1-{[(1S)-4-(carbamoylamino)-1-{[4-({[(2,4-dioxo-6-{[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]amino}-1,2,3,4-tetrahydropyrimidin-5-yl)carbamoyl]oxy}methyl)phenyl]carbamoyl}butyl]carbamoyl}-2-methylpropyl]carbamate

Smiles: CC(C)[C@H](NC(=O)OCC1C2C=CC=CC=2C2C=CC=CC=21)C(=O)N[C@@H](CCCNC(N)=O)C(=O)NC1=CC=C(COC(=O)NC2=C(NC[C@H](O)[C@H](O)[C@H](O)CO)NC(=O)NC2=O)C=C1

InChiKey: HGSKBBAITCBDNC-FAEFUHMUSA-N

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

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: DMSO : 150 mg/mL (165.94 mM; Need ultrasonic)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥12 months if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

In Vitro:

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.

References:

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.
2. 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.
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.

Products are for research use only. Not for human use.