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[Au]/[Ag]-catalysed expedient synthesis of branched heneicosafuranosyl arabinogalactan motif of Mycobacterium tuberculosis cell wall
Emergence of multidrug-resistant and extreme-drug-resistant strains of Mycobacterium tuberculosis (MTb) can cause serious socioeconomic burdens. Arabinogalactan present on the cellular envelope of MTb is unique and is required for its survival; access to arabinogalactan is essential for understandin...
Autores principales: | , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Nature Publishing Group
2017
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5288502/ https://www.ncbi.nlm.nih.gov/pubmed/28120821 http://dx.doi.org/10.1038/ncomms14019 |
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author | Thadke, Shivaji A. Mishra, Bijoyananda Islam, Maidul Pasari, Sandip Manmode, Sujit Rao, Boddu Venkateswara Neralkar, Mahesh Shinde, Ganesh P. Walke, Gulab Hotha, Srinivas |
author_facet | Thadke, Shivaji A. Mishra, Bijoyananda Islam, Maidul Pasari, Sandip Manmode, Sujit Rao, Boddu Venkateswara Neralkar, Mahesh Shinde, Ganesh P. Walke, Gulab Hotha, Srinivas |
author_sort | Thadke, Shivaji A. |
collection | PubMed |
description | Emergence of multidrug-resistant and extreme-drug-resistant strains of Mycobacterium tuberculosis (MTb) can cause serious socioeconomic burdens. Arabinogalactan present on the cellular envelope of MTb is unique and is required for its survival; access to arabinogalactan is essential for understanding the biosynthetic machinery that assembles it. Isolation from Nature is a herculean task and, as a result, chemical synthesis is the most sought after technique. Here we report a convergent synthesis of branched heneicosafuranosyl arabinogalactan (HAG) of MTb. Key furanosylations are performed using [Au]/[Ag] catalysts. The synthesis of HAG is achieved by the repetitive use of three reactions namely 1,2-trans furanoside synthesis by propargyl 1,2-orthoester donors, unmasking of silyl ether, and conversion of n-pentenyl furanosides into 1,2-orthoesters. Synthesis of HAG is achieved in 47 steps (with an overall yield of 0.09%) of which 21 are installation of furanosidic linkages in a stereoselective manner. |
format | Online Article Text |
id | pubmed-5288502 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2017 |
publisher | Nature Publishing Group |
record_format | MEDLINE/PubMed |
spelling | pubmed-52885022017-02-10 [Au]/[Ag]-catalysed expedient synthesis of branched heneicosafuranosyl arabinogalactan motif of Mycobacterium tuberculosis cell wall Thadke, Shivaji A. Mishra, Bijoyananda Islam, Maidul Pasari, Sandip Manmode, Sujit Rao, Boddu Venkateswara Neralkar, Mahesh Shinde, Ganesh P. Walke, Gulab Hotha, Srinivas Nat Commun Article Emergence of multidrug-resistant and extreme-drug-resistant strains of Mycobacterium tuberculosis (MTb) can cause serious socioeconomic burdens. Arabinogalactan present on the cellular envelope of MTb is unique and is required for its survival; access to arabinogalactan is essential for understanding the biosynthetic machinery that assembles it. Isolation from Nature is a herculean task and, as a result, chemical synthesis is the most sought after technique. Here we report a convergent synthesis of branched heneicosafuranosyl arabinogalactan (HAG) of MTb. Key furanosylations are performed using [Au]/[Ag] catalysts. The synthesis of HAG is achieved by the repetitive use of three reactions namely 1,2-trans furanoside synthesis by propargyl 1,2-orthoester donors, unmasking of silyl ether, and conversion of n-pentenyl furanosides into 1,2-orthoesters. Synthesis of HAG is achieved in 47 steps (with an overall yield of 0.09%) of which 21 are installation of furanosidic linkages in a stereoselective manner. Nature Publishing Group 2017-01-25 /pmc/articles/PMC5288502/ /pubmed/28120821 http://dx.doi.org/10.1038/ncomms14019 Text en Copyright © 2017, The Author(s) http://creativecommons.org/licenses/by/4.0/ This work is licensed under a Creative Commons Attribution 4.0 International License. The images or other third party material in this article are included in the article's Creative Commons license, unless indicated otherwise in the credit line; if the material is not included under the Creative Commons license, users will need to obtain permission from the license holder to reproduce the material. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/ |
spellingShingle | Article Thadke, Shivaji A. Mishra, Bijoyananda Islam, Maidul Pasari, Sandip Manmode, Sujit Rao, Boddu Venkateswara Neralkar, Mahesh Shinde, Ganesh P. Walke, Gulab Hotha, Srinivas [Au]/[Ag]-catalysed expedient synthesis of branched heneicosafuranosyl arabinogalactan motif of Mycobacterium tuberculosis cell wall |
title | [Au]/[Ag]-catalysed expedient synthesis of branched heneicosafuranosyl arabinogalactan motif of Mycobacterium tuberculosis cell wall |
title_full | [Au]/[Ag]-catalysed expedient synthesis of branched heneicosafuranosyl arabinogalactan motif of Mycobacterium tuberculosis cell wall |
title_fullStr | [Au]/[Ag]-catalysed expedient synthesis of branched heneicosafuranosyl arabinogalactan motif of Mycobacterium tuberculosis cell wall |
title_full_unstemmed | [Au]/[Ag]-catalysed expedient synthesis of branched heneicosafuranosyl arabinogalactan motif of Mycobacterium tuberculosis cell wall |
title_short | [Au]/[Ag]-catalysed expedient synthesis of branched heneicosafuranosyl arabinogalactan motif of Mycobacterium tuberculosis cell wall |
title_sort | [au]/[ag]-catalysed expedient synthesis of branched heneicosafuranosyl arabinogalactan motif of mycobacterium tuberculosis cell wall |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5288502/ https://www.ncbi.nlm.nih.gov/pubmed/28120821 http://dx.doi.org/10.1038/ncomms14019 |
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