Convenient synthesis of glycosylated hydroxylysine derivatives for use in solid-phase peptide synthesis

Abstract

δ- O-Glycosylated 9-fluorenylmethoxycarbonyl-hydroxylysine (Fmoc-Hyl) derivatives have been conveniently prepared by introduction of a β- d-galactopyranosyl group to copper-complexed Hyl[ε- tert-butyloxycarbonyl (Boc)] or Hyl[ε-allyloxycarbonyl (Aloc)], followed by decomposition of the copper complex and addition of an Fmoc group to the α-amino group. Fmoc-Hyl[ε-Boc, O-(2,3,4,6-tetra- O-acetyl-β- d-galactopyranosyl)] was used in the solid-phase synthesis of a type IV collagen derived sequence.