1007401-37-7Relevant academic research and scientific papers
Synthesis of a galactosylated 4-hydroxylysine building block and its incorporation into a collagen immunodominant glycopeptide
Marin, Julien,Briand, Jean-Paul,Guichard, Gilles
, p. 1005 - 1012 (2008)
An analogue of the immunodominant glycopeptide from type II collagen encompassing residues 256-270 has been prepared by substituting β-D-galactopyranosyl-(2S,4R)-4-hydroxy-L-lysyl (Gal-4-Hyl) for β-D-galactopyranosyl-(2S,5R)-5-hydroxy-L-lysyl (Gal-5-Hyl) at position 264. The synthesis of the 4-hydroxylysine aglycon started from the known (2S,4S)-4-hydroxy-6-oxo-1,2-piperidinedicarboxylate (3) and involved selective ring-opening of 3, lactone formation, and N-acylation of the lactone with glycyl esters. The resulting N-Fmoc-protected 4-hydroxylysyl-glycine dipeptide derivative was galactosylated in high yield to give a building block suitable for solid-phase peptide synthesis. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
