A Rational Synthesis of a Branched Decaarabinofuranoside Related to the Fragments of Mycobacterial Polysaccharides
A rational synthesis of the branched decaarabinofuranoside with 4-(2-azidoethoxy)phenyl aglycone (a Janus aglycone) related to the non-reducing terminal fragments of the arabinogalactan and lipoarabinomannan from <i>Mycobacterium tuberculosis</i> was proposed. Since the most challenging...
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| Format: | Article |
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2025-08-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/30/15/3295 |
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| author | Polina I. Abronina Nelly N. Malysheva Maxim Y. Karpenko Dmitry S. Novikov Alexander I. Zinin N. G. Kolotyrkina Leonid O. Kononov |
| author_facet | Polina I. Abronina Nelly N. Malysheva Maxim Y. Karpenko Dmitry S. Novikov Alexander I. Zinin N. G. Kolotyrkina Leonid O. Kononov |
| author_sort | Polina I. Abronina |
| collection | DOAJ |
| description | A rational synthesis of the branched decaarabinofuranoside with 4-(2-azidoethoxy)phenyl aglycone (a Janus aglycone) related to the non-reducing terminal fragments of the arabinogalactan and lipoarabinomannan from <i>Mycobacterium tuberculosis</i> was proposed. Since the most challenging step is the formation of a 1,2-<i>cis</i> glycosidic linkage, we have significantly simplified access to a library of oligoarabinofuranosides derived from <i>Mycobacterium tuberculosis</i> polysaccharides using a silylated Ara-β-(1→2)-Ara disaccharide as the glycosyl donor. The application of a Janus aglycone also allowed us to reduce the number of reaction steps in glycoside synthesis. The obtained arabinans can be useful to further prepare conjugates as antigens for creating tuberculosis screening assays. |
| format | Article |
| id | doaj-art-222913d3ee0c434fa59e6abcf1be7300 |
| institution | DOAJ |
| issn | 1420-3049 |
| language | English |
| publishDate | 2025-08-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj-art-222913d3ee0c434fa59e6abcf1be73002025-08-20T03:04:43ZengMDPI AGMolecules1420-30492025-08-013015329510.3390/molecules30153295A Rational Synthesis of a Branched Decaarabinofuranoside Related to the Fragments of Mycobacterial PolysaccharidesPolina I. Abronina0Nelly N. Malysheva1Maxim Y. Karpenko2Dmitry S. Novikov3Alexander I. Zinin4N. G. Kolotyrkina5Leonid O. Kononov6N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prosp., 47, Moscow 119991, RussiaN.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prosp., 47, Moscow 119991, RussiaN.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prosp., 47, Moscow 119991, RussiaN.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prosp., 47, Moscow 119991, RussiaN.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prosp., 47, Moscow 119991, RussiaN.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prosp., 47, Moscow 119991, RussiaN.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prosp., 47, Moscow 119991, RussiaA rational synthesis of the branched decaarabinofuranoside with 4-(2-azidoethoxy)phenyl aglycone (a Janus aglycone) related to the non-reducing terminal fragments of the arabinogalactan and lipoarabinomannan from <i>Mycobacterium tuberculosis</i> was proposed. Since the most challenging step is the formation of a 1,2-<i>cis</i> glycosidic linkage, we have significantly simplified access to a library of oligoarabinofuranosides derived from <i>Mycobacterium tuberculosis</i> polysaccharides using a silylated Ara-β-(1→2)-Ara disaccharide as the glycosyl donor. The application of a Janus aglycone also allowed us to reduce the number of reaction steps in glycoside synthesis. The obtained arabinans can be useful to further prepare conjugates as antigens for creating tuberculosis screening assays.https://www.mdpi.com/1420-3049/30/15/3295glycosylation<span style="font-variant: small-caps">d</span>-arabinofuranoseJanus aglyconesilyl group<i>Mycobacterium tuberculosis</i> |
| spellingShingle | Polina I. Abronina Nelly N. Malysheva Maxim Y. Karpenko Dmitry S. Novikov Alexander I. Zinin N. G. Kolotyrkina Leonid O. Kononov A Rational Synthesis of a Branched Decaarabinofuranoside Related to the Fragments of Mycobacterial Polysaccharides Molecules glycosylation <span style="font-variant: small-caps">d</span>-arabinofuranose Janus aglycone silyl group <i>Mycobacterium tuberculosis</i> |
| title | A Rational Synthesis of a Branched Decaarabinofuranoside Related to the Fragments of Mycobacterial Polysaccharides |
| title_full | A Rational Synthesis of a Branched Decaarabinofuranoside Related to the Fragments of Mycobacterial Polysaccharides |
| title_fullStr | A Rational Synthesis of a Branched Decaarabinofuranoside Related to the Fragments of Mycobacterial Polysaccharides |
| title_full_unstemmed | A Rational Synthesis of a Branched Decaarabinofuranoside Related to the Fragments of Mycobacterial Polysaccharides |
| title_short | A Rational Synthesis of a Branched Decaarabinofuranoside Related to the Fragments of Mycobacterial Polysaccharides |
| title_sort | rational synthesis of a branched decaarabinofuranoside related to the fragments of mycobacterial polysaccharides |
| topic | glycosylation <span style="font-variant: small-caps">d</span>-arabinofuranose Janus aglycone silyl group <i>Mycobacterium tuberculosis</i> |
| url | https://www.mdpi.com/1420-3049/30/15/3295 |
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