ISSN:
0947-6539
Keywords:
glycals
;
glycopeptides
;
glycosylations
;
β-mannosides
;
oligosaccharides
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
N-Linked glycopeptides were synthesized by condensation of a highmannose 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.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/chem.19970031011
Permalink
