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

Shivaji A. Thadke, Bijoyananda Mishra, Maidul Islam, Sandip Pasari, Sujit Manmode, Boddu Venkateswara Rao, Mahesh Neralkar, Ganesh P. Shinde, Gulab Walke and Srinivas Hotha ()
Additional contact information
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

Nature Communications, 2017, vol. 8, issue 1, 1-9

Abstract: 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.

Date: 2017
References: Add references at CitEc
Citations:

Downloads: (external link)
https://www.nature.com/articles/ncomms14019 Abstract (text/html)

Related works:
This item may be available elsewhere in EconPapers: Search for items with the same title.

Export reference: BibTeX RIS (EndNote, ProCite, RefMan) HTML/Text

Persistent link: https://EconPapers.repec.org/RePEc:nat:natcom:v:8:y:2017:i:1:d:10.1038_ncomms14019

Ordering information: This journal article can be ordered from
https://www.nature.com/ncomms/

DOI: 10.1038/ncomms14019

Access Statistics for this article

Nature Communications is currently edited by Nathalie Le Bot, Enda Bergin and Fiona Gillespie

More articles in Nature Communications from Nature
Bibliographic data for series maintained by Sonal Shukla () and Springer Nature Abstracting and Indexing ().