10.1021/ja0491836.s001
J. David Warren
J. David
Warren
Justin S. Miller
Justin S.
Miller
Stacy J. Keding
Stacy J.
Keding
Samuel J. Danishefsky
Samuel J.
Danishefsky
Toward Fully Synthetic Glycoproteins by Ultimately Convergent Routes: A
Solution to a Long-Standing Problem
American Chemical Society
2004
bifunctional glycopeptide
convergent technique
acyl donor
approach centers
Synthetic Glycoproteins
convergent segment
acid residue
glycosylated peptides
convergent synthesis
2004-06-02 00:00:00
Journal contribution
https://acs.figshare.com/articles/journal_contribution/Toward_Fully_Synthetic_Glycoproteins_by_Ultimately_Convergent_Routes_A_Solution_to_a_Long_Standing_Problem/3337237
A method is disclosed for the convergent synthesis of multiply glycosylated peptides. The approach centers on a convergent technique for generating masked, complex glycopeptide-containing C-terminal acyl donors. Activation of the latent donor in situ and use directly in segment coupling with a second peptide bearing a complex carbohydrate produces a completely unprotected, bifunctional glycopeptide. The system demonstrates a minimum level of hydrolysis and epimerization at the C-terminal amino acid residue of the acyl donor during fully convergent segment coupling and is therefore a powerful tool for the synthesis of glycoproteins.