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Synthesis of a Galactosylated 4‐Hydroxylysine Building Block and Its Incorporation into a Collagen Immunodominant Glycopeptide
Author(s) -
Marin Julien,
Briand JeanPaul,
Guichard Gilles
Publication year - 2008
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200700806
Subject(s) - chemistry , hydroxylysine , dipeptide , glycopeptide , stereochemistry , acylation , tripeptide , pentapeptide repeat , peptide , derivative (finance) , glycine , yield (engineering) , peptide synthesis , ring (chemistry) , lysine , amino acid , biochemistry , organic chemistry , catalysis , antibiotics , financial economics , economics , materials science , metallurgy
An analogue of the immunodominant glycopeptide from type II collagen encompassing residues 256–270 has been prepared by substituting β‐ D ‐galactopyranosyl‐(2 S ,4 R )‐4‐hydroxy‐ L ‐lysyl (Gal‐4‐Hyl) for β‐ D ‐galactopyranosyl‐(2 S ,5 R )‐5‐hydroxy‐ L ‐lysyl (Gal‐5‐Hyl) at position 264. The synthesis of the 4‐hydroxylysine aglycon started from the known (2 S ,4 S )‐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, 69451 Weinheim, Germany, 2008)
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