The trehalose glycolipid C18Brar promotes antibody and T-cell immune responses to Mannheimia haemolytica and Mycoplasma ovipneumoniae whole cell antigens in sheep
Fig 2
Illustration showing synthesis of C18Brar.
To prepare C18Brar, 2,2’,3,3’,4,4’-hexa-O-trimethylsilyl-α,α’-D-trehalose S1 [56] and 4-octadecyloxy-benzoic acid S2 [38] were treated with N-ethyl-N’-(3-dimethyaminopropyl)carbodiimide (EDCI) and 4-dimethylaminopyridine (DMAP), to form the diester S3 in an 59% yield. The trimethylsilyl ether protecting groups were subsequently removed with acidic Dowex to give C18Brar in 95% yield. Characterization data was consistent with that previously reported [38].