Abstract
| - Synthetic glycoclusters are extensively used as mimetics of naturally occurring, multivalentcarbohydrate ligands in various glycobiological applications. Their preparation, however, is far fromtrivial, and it still is a limiting factor in the study of carbohydrate binding. We herein report thesynthesis of an orthogonally protected building block, N-Alloc-N‘-Boc-N‘ ‘-Fmoc-α,α-bis(aminomethyl)-β-alanine (1), and its use in the preparation of triantennary peptide glycoclusters (21−24)on a solid support. The assembly of the clusters involves removal of the amino protections of thesolid-supported branching unit 1 in the order Fmoc, Boc, and Alloc, and subsequent coupling ofperacetylated O-(glycopyranosyl)-N-Fmoc-l-serine pentafluorophenyl esters (galactose, glucose,mannose, and ribose) to each amino group exposed.
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