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[Au]/[Ag]-catalysed expedient synthesis of branched heneicosafuranosyl arabinogalactan motif of Mycobacterium tuberculosis cell wall

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  • Shivaji A. Thadke

    (Indian Institute of Science Education and Research)

  • Bijoyananda Mishra

    (Indian Institute of Science Education and Research)

  • Maidul Islam

    (Indian Institute of Science Education and Research)

  • Sandip Pasari

    (Indian Institute of Science Education and Research)

  • Sujit Manmode

    (Indian Institute of Science Education and Research)

  • Boddu Venkateswara Rao

    (Indian Institute of Science Education and Research)

  • Mahesh Neralkar

    (Indian Institute of Science Education and Research)

  • Ganesh P. Shinde

    (Indian Institute of Science Education and Research)

  • Gulab Walke

    (Indian Institute of Science Education and Research)

  • Srinivas Hotha

    (Indian Institute of Science Education and Research)

Abstract

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.

Suggested Citation

  • Shivaji A. Thadke & Bijoyananda Mishra & Maidul Islam & Sandip Pasari & Sujit Manmode & Boddu Venkateswara Rao & Mahesh Neralkar & Ganesh P. Shinde & Gulab Walke & Srinivas Hotha, 2017. "[Au]/[Ag]-catalysed expedient synthesis of branched heneicosafuranosyl arabinogalactan motif of Mycobacterium tuberculosis cell wall," Nature Communications, Nature, vol. 8(1), pages 1-9, April.
    • Handle: RePEc:nat:natcom:v:8:y:2017:i:1:d:10.1038_ncomms14019
    DOI: 10.1038/ncomms14019
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