239806-29-2Relevant articles and documents
C-Glycosyl Tyrosines. Synthesis and Incorporation into C-Glycopeptides
Pearce, Alan J.,Ramaya, Sharn,Thorn, Simon N.,Bloomberg, Graham B.,Walter, Daryl S.,Gallagher, Timothy
, p. 5453 - 5462 (2007/10/03)
The synthesis of the Fmoc-protected C-glycosyl tyrosines 1 and 2, together with two other related C-glycosyl tyrosines, has been achieved. Key reactions involved (i) the reaction of a glycal with an organozinc reagent (carrying an aryl iodide function) in the presence of a Lewis acid to establish the C-glycosyl linkage and (ii) subsequent cross coupling of the aryl iodide to an alanyl zinc reagent (in the presence of a Pd(0) catalyst) to complete the construction of the α-amino acid moiety. Using solid-phase peptide synthesis methods, two units of the mannosyl derivative 1 (shown as L-Tyr-[C-Ac4-α-D-Man]) have been incorporated (with four units of glycine) into the linear hexapeptide 3 which was then converted to the C2-symmetric cyclic oligopeptide 4.