Synthesis and antioxidant capacity of novel stable 5-tellurofuranose derivatives

Elton L Borges; Marta T Ignasiak; Yuliia Velichenko; Gelson Perin; Craig A Hutton; Michael J Davies; Carl H Schiesser

doi:10.1039/c8cc00565f

Synthesis and antioxidant capacity of novel stable 5-tellurofuranose derivatives

Chem Commun (Camb). 2018 Mar 25;54(24):2990-2993. doi: 10.1039/c8cc00565f. Epub 2018 Mar 5.

Authors

Elton L Borges¹, Marta T Ignasiak², Yuliia Velichenko³, Gelson Perin⁴, Craig A Hutton³, Michael J Davies⁵, Carl H Schiesser⁶

Affiliations

¹ Dept. of Biomedical Sciences, University of Copenhagen, Panum Institute, Blegdamsvej 3, DK-2200, Copenhagen, Denmark. davies@sund.ku.dk and School of Chemistry and Bio21 Molecular Science and Biotechnology Institute, The University of Melbourne, Victoria 3010, Australia and Laboratório de Síntese Orgânica Limpa-LASOL, Universidade Federal de Pelotas, P.O. Box 354, 96010-900, Pelotas, RS, Brazil.
² Dept. of Biomedical Sciences, University of Copenhagen, Panum Institute, Blegdamsvej 3, DK-2200, Copenhagen, Denmark. davies@sund.ku.dk.
³ School of Chemistry and Bio21 Molecular Science and Biotechnology Institute, The University of Melbourne, Victoria 3010, Australia.
⁴ Laboratório de Síntese Orgânica Limpa-LASOL, Universidade Federal de Pelotas, P.O. Box 354, 96010-900, Pelotas, RS, Brazil.
⁵ Dept. of Biomedical Sciences, University of Copenhagen, Panum Institute, Blegdamsvej 3, DK-2200, Copenhagen, Denmark. davies@sund.ku.dk and Seleno Therapeutics Pty. Ltd, Brighton East, Victoria 3187, Australia. chschiesser@gmail.com.
⁶ Seleno Therapeutics Pty. Ltd, Brighton East, Victoria 3187, Australia. chschiesser@gmail.com.

PMID: 29505059
DOI: 10.1039/c8cc00565f

Abstract

Novel stable tellurium-containing carbohydrate derivatives are prepared from hexitols and pentitols through a double nucleophilic substitution with NaHTe in PEG-400. These tellurosugars react at very high rates with two-electron oxidants, including hypochlorous and peroxynitrous acid, formed at sites of inflammation, and show considerable promise as protective agents against oxidative damage.