6533b81ffe1ef96bd1277092

RESEARCH PRODUCT

ChemInform Abstract: SYNTHESIS OF THE GLYCOPEPTIDE PARTIAL SEQUENCE A80-A84 OF HUMAN FIBROBLAST INTERFERON

Horst KunzHerbert Waldmann

subject

TrisStereochemistryChemistryfood and beverageschemistry.chemical_elementSequence (biology)General MedicineChlorideGlycopeptideRhodiumCatalysischemistry.chemical_compoundmedicineTriphenylphosphinemedicine.drugPalladium

description

The glycopentapeptide H-(GlcNAcβ1-)Asn-Glu-Thr-Ile-Val-OH (10) representing the partial sequence A80–A84 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.

https://doi.org/10.1002/chin.198535293