Synthesis, stabilization, and characterization of the MR1 ligand precursor 5-amino-6-D-ribitylaminouracil (5-A-RU)

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  • Li, K.
    • Affiliation: Eshelman School of Pharmacy, Division of Chemical Biology and Medicinal Chemistry
  • Vorkas, C.K.
    • Other Affiliation: Sloan Kettering Institute
  • Chaudhry, A.
    • Other Affiliation: Sloan Kettering Institute
  • Bell, D.L.
    • Other Affiliation: Emory University School of Medicine
  • Willis, R.A.
    • Other Affiliation: Memorial Sloan Kettering Cancer Center
  • Rudensky, A.
    • Other Affiliation: Sloan Kettering Institute
  • Altman, J.D.
    • Other Affiliation: Emory University School of Medicine
  • Glickman, M.S.
    • Other Affiliation: Sloan Kettering Institute
  • Aubé, J.
    • Affiliation: Eshelman School of Pharmacy, Division of Chemical Biology and Medicinal Chemistry
Abstract
  • Mucosal-associated invariant T (MAIT) cells are an abundant class of innate T cells restricted by the MHC I-related molecule MR1. MAIT cells can recognize bacterially-derived metabolic intermediates from the riboflavin pathway presented by MR1 and are postulated to play a role in innate antibacterial immunity through production of cytokines and direct bacterial killing. MR1 tetramers, typically stabilized by the adduct of 5-amino-6-D-ribitylaminour-acil (5-A-RU) and methylglyoxal (MeG), are important tools for the study of MAIT cells. A long-standing problem with 5-A-RU is that it is unstable upon storage. Herein we report an efficient synthetic approach to the HCl salt of this ligand, which has improved stability during storage. We also show that synthetic 5-A-RU•HCl produced by this method may be used in protocols for the stimulation of human MAIT cells and production of both human and mouse MR1 tetramers for MAIT cell identification.
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  • Article
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  • In Copyright
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  • Attribution 4.0 International
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  • PLoS ONE
Journal volume
  • 13
Journal issue
  • 2
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  • English
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  • 1932-6203
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  • Public Library of Science

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