A highly convergent total synthetic route to glycopeptides carrying a high-mannose core pentasaccharide domain N-linked to a natural peptide motif Journal Article

  


Authors: Danishefsky, S. J.; Hu, S.; Cirillo, P. F.; Eckhardt, M.; Seeberger, P. H.
Article Title: A highly convergent total synthetic route to glycopeptides carrying a high-mannose core pentasaccharide domain N-linked to a natural peptide motif
Abstract: N-Linked glycopeptides were synthesized by condensation of a high-mannose anomeric amine bearing a pentasaccharide with aspartic-acid-containing tri- and pentapeptides through the agency of IIDQ. The pentasaccharide portion, corresponding to the 'core' region of all asparagine-linked glycoproteins, was assembled by means of glycal-derived thioethyl donors and glycal acceptors. The central mannose residue was established by inversion of the C2 hydroxyl of a glucosyl precursor in the pentasaccharide. The protecting-group scheme employed allows the extension of the pentasaccharide through the terminal mannose units. While a fully convergent coupling of the high-mannose carbohydrate to the peptide domain has thus been accomplished for the first time with a fully synthetic sugar, the stereochemical integrity of the anomeric center of the carbohydrate domain was not maintained and a mixture of glycopeptides was obtained.
Keywords: glycosylations; glycopeptides; oligosaccharides; glycals; β-mannosides
Journal Title: Chemistry - A European Journal
Volume: 3
Issue: 10
ISSN: 0947-6539
Publisher: Wiley V C H Verlag Gmbh  
Date Published: 1997-01-01
Start Page: 1617
End Page: 1628
Language: English
PROVIDER: scopus
DOI/URL:

https://www.scopus.com/inward/record.uri?eid=2-s2.0-0030768522&partnerID=40&md5=5c0f1f33af3a146a92b93f22200067bc
Notes: Article -- Export Date: 17 March 2017 -- Source: Scopus