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Synthesis of the Staphylococcus aureus Strain M Capsular Polysaccharide Repeating Unit
[Image: see text] The synthesis of the Staphylococcus aureus strain M capsular polysaccharide repeating unit is reported. A postglycosylation oxidation strategy was utilized for the construction of the α-galactosaminuronic acid linkages, relying on a stereoselective 2-azido-4,6-O-di-tert-butylsilyli...
| Autores principales: | , , , , , |
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| Formato: | Online Artículo Texto |
| Lenguaje: | English |
| Publicado: |
American Chemical Society
2017
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| Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5442609/ https://www.ncbi.nlm.nih.gov/pubmed/28485610 http://dx.doi.org/10.1021/acs.orglett.7b00747 |
| _version_ | 1783238432657506304 |
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| author | Hagen, Bas van Dijk, J. Hessel M. Zhang, Qingju Overkleeft, Herman S. van der Marel, Gijsbert A. Codée, Jeroen D. C. |
| author_facet | Hagen, Bas van Dijk, J. Hessel M. Zhang, Qingju Overkleeft, Herman S. van der Marel, Gijsbert A. Codée, Jeroen D. C. |
| author_sort | Hagen, Bas |
| collection | PubMed |
| description | [Image: see text] The synthesis of the Staphylococcus aureus strain M capsular polysaccharide repeating unit is reported. A postglycosylation oxidation strategy was utilized for the construction of the α-galactosaminuronic acid linkages, relying on a stereoselective 2-azido-4,6-O-di-tert-butylsilylidene galactopyranoside donor, for which the selectivity was assessed by model glycosylations. The α-fucosamine linkage was installed stereoselectively, using a reactive 2-azidofucosyl donor. An unexpected glycosidic bond cleavage during the TEMPO/PhI(OAc)(2)-mediated oxidation of a disaccharide intermediate was circumvented by a TEMPO/PhI(OAc)(2)–Pinnick oxidation protocol. |
| format | Online Article Text |
| id | pubmed-5442609 |
| institution | National Center for Biotechnology Information |
| language | English |
| publishDate | 2017 |
| publisher | American Chemical Society |
| record_format | MEDLINE/PubMed |
| spelling | pubmed-54426092017-05-26 Synthesis of the Staphylococcus aureus Strain M Capsular Polysaccharide Repeating Unit Hagen, Bas van Dijk, J. Hessel M. Zhang, Qingju Overkleeft, Herman S. van der Marel, Gijsbert A. Codée, Jeroen D. C. Org Lett [Image: see text] The synthesis of the Staphylococcus aureus strain M capsular polysaccharide repeating unit is reported. A postglycosylation oxidation strategy was utilized for the construction of the α-galactosaminuronic acid linkages, relying on a stereoselective 2-azido-4,6-O-di-tert-butylsilylidene galactopyranoside donor, for which the selectivity was assessed by model glycosylations. The α-fucosamine linkage was installed stereoselectively, using a reactive 2-azidofucosyl donor. An unexpected glycosidic bond cleavage during the TEMPO/PhI(OAc)(2)-mediated oxidation of a disaccharide intermediate was circumvented by a TEMPO/PhI(OAc)(2)–Pinnick oxidation protocol. American Chemical Society 2017-05-09 2017-05-19 /pmc/articles/PMC5442609/ /pubmed/28485610 http://dx.doi.org/10.1021/acs.orglett.7b00747 Text en Copyright © 2017 American Chemical Society This is an open access article published under a Creative Commons Non-Commercial No Derivative Works (CC-BY-NC-ND) Attribution License (http://pubs.acs.org/page/policy/authorchoice_ccbyncnd_termsofuse.html) , which permits copying and redistribution of the article, and creation of adaptations, all for non-commercial purposes. |
| spellingShingle | Hagen, Bas van Dijk, J. Hessel M. Zhang, Qingju Overkleeft, Herman S. van der Marel, Gijsbert A. Codée, Jeroen D. C. Synthesis of the Staphylococcus aureus Strain M Capsular Polysaccharide Repeating Unit |
| title | Synthesis of the Staphylococcus aureus Strain M Capsular Polysaccharide Repeating Unit |
| title_full | Synthesis of the Staphylococcus aureus Strain M Capsular Polysaccharide Repeating Unit |
| title_fullStr | Synthesis of the Staphylococcus aureus Strain M Capsular Polysaccharide Repeating Unit |
| title_full_unstemmed | Synthesis of the Staphylococcus aureus Strain M Capsular Polysaccharide Repeating Unit |
| title_short | Synthesis of the Staphylococcus aureus Strain M Capsular Polysaccharide Repeating Unit |
| title_sort | synthesis of the staphylococcus aureus strain m capsular polysaccharide repeating unit |
| url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5442609/ https://www.ncbi.nlm.nih.gov/pubmed/28485610 http://dx.doi.org/10.1021/acs.orglett.7b00747 |
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