Synthesis of the pentasaccharide core structure of asparagine-linked glycoprotein oligosaccharides by the glycal assembly method Conference Paper
| Authors: | Seeberger, P. H.; Cirillo, P. F.; Hu, S.; Beebe, X.; Bilodeau, M. T.; Danishefsky, S. J. |
| Title: | Synthesis of the pentasaccharide core structure of asparagine-linked glycoprotein oligosaccharides by the glycal assembly method |
| Conference Title: | 7th International Symposium on Chiral Discrimination (ISCD) |
| Abstract: | The "core" pentasaccharide region of high mannose asparagine-linked glycoproteins was synthesized using thioethyl donors and methyl triflate to promote coupling. All monosaccharide units were prepared from glycals. The central mannose residue was installed by inversion of the C2 hydroxyl of a glucosyl precursor. The protecting group scheme employed allows for the extension of the pentasaccharide through the terminal mannose units and a peptide can be coupled through transformation of the glycal. © 1996 OPA(Overseas Publishers Association) Amsterdam B.V. Published in The Netherlands under license by Gordon and Breach Science Publishers. |
| Keywords: | mass spectrometry; chemistry; magnetic resonance spectroscopy; nuclear magnetic resonance spectroscopy; polysaccharide; polysaccharides; glycoproteins; glycoprotein; thin layer chromatography; infrared spectroscopy; synthesis; asparagine; mesylates; thiol derivative; oligosaccharide synthesis; spectroscopy, fourier transform infrared; n-linked glycoproteins; sulfhydryl compounds; mannose; glycal assembly method; chromatography, thin layer; optical rotation; article; high mannose core structure; thiodonor couplings; mesylic acid derivative; trifluoromethanesulfonic acid methyl ester |
| Journal Title | Enantiomer |
| Volume: | 1 |
| Issue: | 4-6 |
| Conference Dates: | 1995 Nov 12-16 |
| Conference Location: | Jerusalem, Israel |
| ISBN: | 1024-2430 |
| Publisher: | Taylor & Francis Group |
| Date Published: | 1996-01-01 |
| Start Page: | 311 |
| End Page: | 323 |
| Language: | English |
| PUBMED: | 9676275 |
| PROVIDER: | scopus |
| DOI/URL: | |
| Notes: | Article -- Export Date: 22 November 2017 -- Source: Scopus |
