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Synthesis of the Glycopeptide Partial Sequence A 80 –A 84 of Human Fibroblast Interferon
Author(s) -
Kunz Horst,
Waldmann Herbert
Publication year - 1985
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19850680314
Subject(s) - chemistry , triphenylphosphine , glycopeptide , sequence (biology) , fibroblast , glycoprotein , rhodium , peptide , catalysis , palladium , chloride , stereochemistry , medicinal chemistry , organic chemistry , biochemistry , in vitro , antibiotics
The glycopentapeptide H‐(GlcNAcβ1‐)Asn‐Glu‐Thr‐Ile‐Val‐OH ( 10 ) representing the partial sequence A 80 –A 84 of human fibroblast interferon was synthesized using the newly developed allyl‐ester protection of carboxy functions. The allyl esters, which are stable to acids and to bases, can be cleaved under very mild, neutral conditions using tris(triphenylphosphine)rhodium(I) chloride or tetrakis(triphenylphosphine)palladium(0) as a catalyst. This synthetic method opens up a preparative route to glycopeptide model structures of glycoproteins of high biological interest.