Synthesis of N-glycan oxazolines: donors for endohexosaminidase catalysed glycosylation.
Oxazoline mono-, di-, tri- and hexasaccharides, corresponding to the core components of N-linked glycoprotein high mannose glycans, are synthesised as potential glycosyl donors for endohexosaminidase catalysed glycosylation of glycopeptides and glycoprotein remodelling. The crucial beta-D-Manp-(1--&...
| Main Authors: | , , , , , |
|---|---|
| Format: | Journal article |
| Language: | English |
| Published: |
2006
|
| _version_ | 1826260919888379904 |
|---|---|
| author | Rising, T Claridge, T Davies, N Gamblin, D Moir, J Fairbanks, A |
| author_facet | Rising, T Claridge, T Davies, N Gamblin, D Moir, J Fairbanks, A |
| author_sort | Rising, T |
| collection | OXFORD |
| description | Oxazoline mono-, di-, tri- and hexasaccharides, corresponding to the core components of N-linked glycoprotein high mannose glycans, are synthesised as potential glycosyl donors for endohexosaminidase catalysed glycosylation of glycopeptides and glycoprotein remodelling. The crucial beta-D-Manp-(1-->4)-D-GlcpNAc linkage is synthesised via epimerisation of gluco disaccharide substrates by sequential triflation and nucleophilic substitution. Oxazolines are formed directly from the anomeric OPMP protected N-acetyl glucosamine derivatives. Efficient endohexosaminidase catalysed glycosylation of a synthetic beta-D-GlcpNAcAsn glycosyl amino acid is demonstrated with the trisaccharide oxazoline donor. |
| first_indexed | 2024-03-06T19:13:22Z |
| format | Journal article |
| id | oxford-uuid:1788f38e-fa72-4331-b296-64936d90497a |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-06T19:13:22Z |
| publishDate | 2006 |
| record_format | dspace |
| spelling | oxford-uuid:1788f38e-fa72-4331-b296-64936d90497a2022-03-26T10:37:52ZSynthesis of N-glycan oxazolines: donors for endohexosaminidase catalysed glycosylation.Journal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:1788f38e-fa72-4331-b296-64936d90497aEnglishSymplectic Elements at Oxford2006Rising, TClaridge, TDavies, NGamblin, DMoir, JFairbanks, AOxazoline mono-, di-, tri- and hexasaccharides, corresponding to the core components of N-linked glycoprotein high mannose glycans, are synthesised as potential glycosyl donors for endohexosaminidase catalysed glycosylation of glycopeptides and glycoprotein remodelling. The crucial beta-D-Manp-(1-->4)-D-GlcpNAc linkage is synthesised via epimerisation of gluco disaccharide substrates by sequential triflation and nucleophilic substitution. Oxazolines are formed directly from the anomeric OPMP protected N-acetyl glucosamine derivatives. Efficient endohexosaminidase catalysed glycosylation of a synthetic beta-D-GlcpNAcAsn glycosyl amino acid is demonstrated with the trisaccharide oxazoline donor. |
| spellingShingle | Rising, T Claridge, T Davies, N Gamblin, D Moir, J Fairbanks, A Synthesis of N-glycan oxazolines: donors for endohexosaminidase catalysed glycosylation. |
| title | Synthesis of N-glycan oxazolines: donors for endohexosaminidase catalysed glycosylation. |
| title_full | Synthesis of N-glycan oxazolines: donors for endohexosaminidase catalysed glycosylation. |
| title_fullStr | Synthesis of N-glycan oxazolines: donors for endohexosaminidase catalysed glycosylation. |
| title_full_unstemmed | Synthesis of N-glycan oxazolines: donors for endohexosaminidase catalysed glycosylation. |
| title_short | Synthesis of N-glycan oxazolines: donors for endohexosaminidase catalysed glycosylation. |
| title_sort | synthesis of n glycan oxazolines donors for endohexosaminidase catalysed glycosylation |
| work_keys_str_mv | AT risingt synthesisofnglycanoxazolinesdonorsforendohexosaminidasecatalysedglycosylation AT claridget synthesisofnglycanoxazolinesdonorsforendohexosaminidasecatalysedglycosylation AT daviesn synthesisofnglycanoxazolinesdonorsforendohexosaminidasecatalysedglycosylation AT gamblind synthesisofnglycanoxazolinesdonorsforendohexosaminidasecatalysedglycosylation AT moirj synthesisofnglycanoxazolinesdonorsforendohexosaminidasecatalysedglycosylation AT fairbanksa synthesisofnglycanoxazolinesdonorsforendohexosaminidasecatalysedglycosylation |