Convergent synthesis of the pentasaccharide repeating unit of the biofilms produced by Klebsiella pneumoniae
A pentasaccharide repeating unit containing α-linked D-glucuronic acid, β-linked D-mannose, corresponding to the repeating unit of biofilms produced by Klebsiella pneumoniae, has been synthesized using a stereoselective [2 + 3] convergent glycosylation strategy. The β-D-mannosidic moiety has been sy...
| Main Authors: | , , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2019-02-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.15.37 |
| _version_ | 1819179854460878848 |
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| author | Arin Gucchait Angana Ghosh Anup Kumar Misra |
| author_facet | Arin Gucchait Angana Ghosh Anup Kumar Misra |
| author_sort | Arin Gucchait |
| collection | DOAJ |
| description | A pentasaccharide repeating unit containing α-linked D-glucuronic acid, β-linked D-mannose, corresponding to the repeating unit of biofilms produced by Klebsiella pneumoniae, has been synthesized using a stereoselective [2 + 3] convergent glycosylation strategy. The β-D-mannosidic moiety has been synthesized using a D-mannose-derived thioglycoside by a two-step activation process. Late stage TEMPO-mediated oxidation of the pentasaccharide derivative using phase-transfer reaction conditions furnished the target compound in satisfactory yield. |
| first_indexed | 2024-12-22T22:05:04Z |
| format | Article |
| id | doaj.art-c8d7e3fbac7f443295f3970e8358c187 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-22T22:05:04Z |
| publishDate | 2019-02-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-c8d7e3fbac7f443295f3970e8358c1872022-12-21T18:11:01ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972019-02-0115143143610.3762/bjoc.15.371860-5397-15-37Convergent synthesis of the pentasaccharide repeating unit of the biofilms produced by Klebsiella pneumoniaeArin Gucchait0Angana Ghosh1Anup Kumar Misra2Bose Institute, Division of Molecular Medicine, P-1/12, C.I.T. Scheme VII M, Kolkata 700054, IndiaBose Institute, Division of Molecular Medicine, P-1/12, C.I.T. Scheme VII M, Kolkata 700054, IndiaBose Institute, Division of Molecular Medicine, P-1/12, C.I.T. Scheme VII M, Kolkata 700054, IndiaA pentasaccharide repeating unit containing α-linked D-glucuronic acid, β-linked D-mannose, corresponding to the repeating unit of biofilms produced by Klebsiella pneumoniae, has been synthesized using a stereoselective [2 + 3] convergent glycosylation strategy. The β-D-mannosidic moiety has been synthesized using a D-mannose-derived thioglycoside by a two-step activation process. Late stage TEMPO-mediated oxidation of the pentasaccharide derivative using phase-transfer reaction conditions furnished the target compound in satisfactory yield.https://doi.org/10.3762/bjoc.15.37beta-D-mannosidebiofilmsD-glucuronic acidglycosylationKlebsiella pneumoniaepentasaccharidepolysaccharide |
| spellingShingle | Arin Gucchait Angana Ghosh Anup Kumar Misra Convergent synthesis of the pentasaccharide repeating unit of the biofilms produced by Klebsiella pneumoniae Beilstein Journal of Organic Chemistry beta-D-mannoside biofilms D-glucuronic acid glycosylation Klebsiella pneumoniae pentasaccharide polysaccharide |
| title | Convergent synthesis of the pentasaccharide repeating unit of the biofilms produced by Klebsiella pneumoniae |
| title_full | Convergent synthesis of the pentasaccharide repeating unit of the biofilms produced by Klebsiella pneumoniae |
| title_fullStr | Convergent synthesis of the pentasaccharide repeating unit of the biofilms produced by Klebsiella pneumoniae |
| title_full_unstemmed | Convergent synthesis of the pentasaccharide repeating unit of the biofilms produced by Klebsiella pneumoniae |
| title_short | Convergent synthesis of the pentasaccharide repeating unit of the biofilms produced by Klebsiella pneumoniae |
| title_sort | convergent synthesis of the pentasaccharide repeating unit of the biofilms produced by klebsiella pneumoniae |
| topic | beta-D-mannoside biofilms D-glucuronic acid glycosylation Klebsiella pneumoniae pentasaccharide polysaccharide |
| url | https://doi.org/10.3762/bjoc.15.37 |
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