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Literature DB >> 28966658

β-D-Arabinosyl 1-C-sulfonic acid^.

Abstract

A short synthetic route to β,d-arabinofuranosyl 1-C-sulfonic acid (7), a possible biomimetic for the arabinofuranosyl anomeric phosphate, is described. The furanosyl 1-C-sulfonate was prepared by buffered DMDO oxidation of an S-acetyl-1-thio-β-arabinofuranose derivative. Deprotection under mild conditions allowed isolation of the free sulfonic acid without desulfonylation.

Entities: Chemical Disease Species

Keywords: arabinogalactin; arabinosyltransferase; bioisostere; thioacetate; tuberculosis

Year: 2012 PMID： 28966658 PMCID： PMC5621591 DOI： 10.1080/17415993.2012.706814

Source DB: PubMed Journal: J Sulphur Chem ISSN： 1741-5993 Impact factor: 2.680

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References

19 in total

1. Synthesis and antituberculosis activity of C-phosphonate analogues of decaprenolphosphoarabinose, a key intermediate in the biosynthesis of mycobacterial arabinogalactan and lipoarabinomannan.

Authors: Charla A Centrone; Todd L Lowary
Journal: J Org Chem Date: 2002-12-13 Impact factor: 4.354

2. Stereoselective synthesis of 9-beta-d-arabianofuranosyl guanine and 2-amino-9-(beta-d-arabianofuranosyl)purine.

Authors: Xue-Jun Yu; Gai-Xia Li; Xiou-Xiang Qi; You-Quan Deng
Journal: Bioorg Med Chem Lett Date: 2005-02-01 Impact factor: 2.823

3. Stereocontrolled syntheses of deoxyribonucleosides via photoinduced electron-transfer deoxygenation of benzoyl-protected ribo- and arabinonucleosides.

Authors: Z Wang; D R Prudhomme; J R Buck; M Park; C J Rizzo
Journal: J Org Chem Date: 2000-09-22 Impact factor: 4.354

β-D-Arabinosyl 1-C-sulfonic acid^.

1. Synthesis and antituberculosis activity of C-phosphonate analogues of decaprenolphosphoarabinose, a key intermediate in the biosynthesis of mycobacterial arabinogalactan and lipoarabinomannan.

2. Stereoselective synthesis of 9-beta-d-arabianofuranosyl guanine and 2-amino-9-(beta-d-arabianofuranosyl)purine.

3. Stereocontrolled syntheses of deoxyribonucleosides via photoinduced electron-transfer deoxygenation of benzoyl-protected ribo- and arabinonucleosides.

4. Non-isosteric C-glycosyl analogues of natural nucleotide diphosphate sugars as glycosyltransferase inhibitors.

5. Synthesis of Arabino glycosyl triazoles as potential inhibitors of mycobacterial cell wall biosynthesis.

6. The Anomeric Pudovik Rearrangement.

7. Sulfone and phosphinic acid analogs of decaprenolphosphoarabinose as potential anti-tuberculosis agents.

8. Synthesis of S-glycosyl primary sulfonamides.

9. New glycomimetics: anomeric sulfonates, sulfenamides, and sulfonamides.

10. An efficient route for the synthesis of glycosyl phosphinic acids.