Synthesis of base-modified dihydropacidamycins

Bioorganic & Medicinal Chemistry Letters
Rémy C LemoineS J Hecker

Abstract

We describe in this paper the synthesis of 1,2-di-O-acetyl-5-azido-3,5-dideoxy-alpha,beta-L-arabinofuranose, a carbohydrate donor that was used for the synthesis of 1-(5'-amino-3',5'-dideoxy-alpha-L-arabinofuranosyl)uracil, the nucleoside found in dihydropacidamycin D. The carbohydrate donor was also used for the synthesis of a set of new nucleosides that were introduced in new dihydropacidamycins. These compounds were tested for biological activity, and the results showed that uracil is the only base recognized by MraY.

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Citations

Dec 27, 2011·The Journal of Organic Chemistry·Kazuya OkamotoAkira Matsuda
Sep 10, 2011·Organic Letters·Kazuya OkamotoAkira Matsuda
Sep 9, 2016·Journal of Medicinal Chemistry·Michaela SerpiFabrizio Pertusati
Mar 5, 2015·Chemical Society Reviews·Sherif I ElshahawiJon S Thorson
Mar 23, 2020·Journal of Molecular Biology·Ellene H Mashalidis, Seok-Yong Lee
Apr 9, 2008·Organic Letters·Sanzhong LuoJin-Pei Cheng

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