166668-33-3Relevant articles and documents
HYCRON, an Allylic Anchor for High-Efficiency Solid Phase Synthesis of Protected Peptides and Glycopeptides
Seitz, Oliver,Kunz, Horst
, p. 813 - 826 (2007/10/03)
The recently developed allylic HYCRON anchor1 exhibits excellent properties for the solid phase synthesis of protected peptides and glycopeptides. Model reactions with analogous low molecular weight compounds assessed the acid- and base-stability of the polar and flexible HYCRON linkage. The new anchor is available in a two-step synthesis and allows the use of both the Boc- and the Fmoc-strategy, which can even be combined within one synthesis. Protected glycopeptides are released under almost neutral conditions, taking advantage of the Pd(0)-catalyzed allyl transfer to a weakly basic nucleophile such as N-methylaniline. The highly efficient synthesis of O-αGalNAc-(TN)-peptides of the MUC-1 repeating unit is described. Acid- and base-stability of the allyl ester linkage enabled the synthesis of an O-glucosylated peptide by first removing a threonine tert-butyl group on the solid phase and subsequently glycosylating the liberated resin-bound hydroxyl component.
Ein neuer allylischer Anker fuer die Festphasensynthese - Synthese von geschuetzten und ungeschuetzten O-Glycopeptiden des Mucintyps
Seitz, Oliver,Kunz, Horst
, p. 901 - 904 (2007/10/02)
Stichworte: Festphasensynthese * Glycopeptide * Peptide