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Synthese von L ‐Prolin‐haltigen O‐Glycopeptiden
Author(s) -
Paulsen Hans,
Merz Gunnar,
Brockhausen Inka
Publication year - 1990
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.1990199001138
Subject(s) - chemistry , glycopeptide , proline , steric effects , stereochemistry , pyranose , threonine , amino acid , biochemistry , enzyme , serine , antibiotics
Synthesis of L ‐Proline‐Containing O‐Glycopeptides The synthesis of a number of L ‐proline‐containing O‐glycopeptides in which 2‐acetamido‐2‐deoxy‐α‐ D ‐ galacto ‐pyranose is α‐glycosidically linked to L ‐threonine is described. For N‐terminal extension with amino acids the building block 3 is preferred. For C‐terminal extension a new intermediate is developed, that includes the Aloc/tBu combination of protective groups which can be synthesized with high yield and stereoselectivity. The Aloc group shows a low steric hindrance and is very stable. Therefore, the carbohydrate‐containing compound 68 can also be coupled C‐terminally with low‐reactive L ‐proline derivatives in good yields. The synthesized O‐glycopeptides shall be used in the investigation of the dependence of the protein structure on the glycosyltransferase activity of the biosyntheses of mucins.