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A Novel Allylic Anchor for Solid‐Phase Synthesis—Synthesis of Protected and Unprotected O‐Glycosylated Mucin‐Type Glycopeptides
Author(s) -
Seitz Oliver,
Kunz Horst
Publication year - 1995
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199508031
Subject(s) - glycopeptide , allylic rearrangement , combinatorial chemistry , chemistry , mucin , catalysis , stereochemistry , organic chemistry , biochemistry , antibiotics
An efficient solid‐phase synthesis of glycopeptides is achieved with the new anchor HYCRON, which combines an allylic ester with the flexible, solubilizing triethyleneglycol spacer. Acid‐ and base‐stability of the allylic anchor enables both Fmoc and Boc strategies to be used. The partially protected glycopeptides can be cleaved from the support by Pd 0 catalysis under virtually neutral conditions in high yields (about 95%) and purity (>95%). AMPS = aminomethylpolystyrene.