Stereoselective synthesis of β-linked TBDMS-protected chitobiose-asparagine:: a versatile building block for amyloidogenic glycopeptides

A simple and efficient synthesis of a Fmoc-L-Asn[beta -chitobiose(TBDMS)(5)]-OH with selectivity for the beta -linked carbohydrate is described. The Utility Of this building block is illustrated in the synthesis of a glycosylated amyloidogenic peptide representing the 175-195(+) fragment of the mouse prion protein (PrPGP). (C) 2001 Elsevier Science Ltd. All rights reserved.