Synthesis of N-epsilon-lithocholyl-L-lysine, a component of tissue-bound lithocholic acid, via lithocholyl-N-hydroxysuccinimide.
N-epsilon-lithocholyl-l-lysine is a lithocholic acid modified lysine residue found in proteins from tissues. This paper describes the synthesis of this compound as well as that of the isomeric N-alpha-lithocholyl-l-lysine and the di-substituted N-alpha-epsilon-bis-lithocholyl-l-lysine. The procedure involves the initial coupling of lithocholyl-N-hydroxysuccinimide to the appropriate N-alpha- or N-epsilon-CBZ (carbobenzloxy) protected lysine derivative followed by hydrogenolysis with palladium black of the CBZ group using formic acid as the hydrogen donor.
D002855:Chromatography, Thin Layer; D008095:Lithocholic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D013388:Succinimides
D013388:Succinimides; C047106:lithocholyl-N-hydroxysuccinimide; D008095:Lithocholic Acid; C044419:N-epsilon-lithocholyllysine