762275-46-7Relevant academic research and scientific papers
Galactosylated 5-hydroxylysine mimetics for glycopeptide synthesis
Marin, Julien,Violette, Aude,Briand, Jean-Paul,Guichard, Gilles
, p. 3027 - 3039 (2004)
The design and synthesis of four galactosylated 5-hydroxylysine mimetic building blocks (2-5), conveniently protected for solid-phase glycopeptide synthesis, is described. Our approach features: i) a short and divergent route to the corresponding protected amino acid aglycons 6-9 that involves selective ring-opening of enantiopure 5-hydroxylated 6-oxo-1,2-piperidinedicarboxylate 10 and 11 with sodium borohydride in ethanol with formation of the corresponding 1,2-diol; ii) a common δ-lactam precursor 12, readily accessible from Boc-Asp-OtBu (3 steps, 74% yield), that can be hydroxylated with a high level of asymmetric induction; iii) the use of tetrapivaloylated galactosyl bromide as galactosyl donor to avoid or limit orthoester formation. The four galactosylated hydroxylysine analogues 2-5 are suitable building blocks for incorporation into immunodominant peptides derived from type II collagen (CII) and for future investigations aimed at determining the fine specificity of arthritogenic T-cells in collagen-induced arthritis (CIA), a mouse model for rheumatoid arthritis (RA). Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
