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Eine neue Strategie zur Festphasensynthese von O ‐Glycopeptiden über 2‐Azidoglycopeptide
Author(s) -
Paulsen Hans,
Bielfeldt Tim,
Peters Stefan,
Meldal Morten,
Bock Klaus
Publication year - 1994
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.199419940410
Subject(s) - glycopeptide , chemistry , residue (chemistry) , solid phase synthesis , hydrate , hydrazine (antidepressant) , cleavage (geology) , chromatography , combinatorial chemistry , organic chemistry , peptide , biochemistry , geotechnical engineering , fracture (geology) , engineering , antibiotics
A New Strategy for the Solid‐Phase Synthesis of O ‐Glycopeptides via 2‐Azido‐glycopeptides The building blocks Fmoc‐Thr(α‐ D ‐GalN 3 Ac 3 )‐OPfp ( 8 ) and Fmoc‐Ser(α‐ D ‐GalN 3 Ac 3 )‐OPfp ( 9 ) were synthesized. Both building blocks are active esters which can directly be used for the solid‐phase synthesis of O ‐glycopeptides. The obtained glycopeptides carry an 2‐azido‐2‐deoxy‐ D ‐galactosyl residue α‐linked to Thr or Ser. The conversion of the 2‐azido into the 2‐acetamido groups was achieved with thioacetic acid on solid support, and subsequently the sugar residues of the polymer bound glycopeptides were deacetylated with hydrazine hydrate in methanol. The subsequent cleavage from the resin with TFA/water gave after RP‐HPLC purification directly the desired deprotected O ‐glycopeptides.