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

delta-O-Glycosylated 9-fluorenylmethoxycarbonyl-hydroxylysine (Fmoc-Hyl) de rivatives have been conveniently prepared by introduction of a beta-D-galac topyranosyl group to copper-complexed Hyl[epsilon-tert-butyloxycarbonyl (Bo c)] or Hyl[epsilon-allyloxycarbonyl (Aloc)], followed by decomposition of t he copper complex and addition of an Fmoc group to the alpha-amino group. F moc-Hyl[epsilon-Boc,O-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)] was used in the solid-phase synthesis of a type IV collagen derived sequence. (C) 2000 Elsevier Science Ltd. All rights reserved.