Issue 18, 2003
From the journal:

Organic & Biomolecular Chemistry

Efficient synthesis of glycosylated phenazine natural products and analogs with DISAL (methyl 3,5-dinitrosalicylate) glycosyl donors†

Jane B. Laursen,ab   Lars Petersen,b   Knud J. Jensen*a  and  John Nielsen*a  

* Corresponding authors

a Department of Chemistry, The Royal Veterinary and Agricultural University, DK-1871 Frederiksberg C, Denmark
E-mail: kjj@kvl.dk, jn@kvl.dk
Fax: +45 35 28 23 98
Tel: +45 35 28 24 28

b Department of Chemistry, Technical University of Denmark, DK-2800 Kgs. Lyngby, Denmark

Abstract

Inspired by the occurrence and function of phenazines in natural products, new glycosylated analogs were designed and synthesized. DISAL (methyl 3,5-dinitrosalicylate) glycosyl donors were used in an efficient and easily-handled glycosylation protocol compatible with combinatorial chemistry. Benzoylated D-glucose, D-galactose and L-quinovose DISAL glycosyl donors were synthesized in high yields and used under mild conditions to glycosylate methyl saphenate and 2-hydroxyphenazine. The glycosides were screened for biological activity and one compound showed inhibitory activity towards topoisomerase II.

Graphical abstract: Efficient synthesis of glycosylated phenazine natural products and analogs with DISAL (methyl 3,5-dinitrosalicylate) glycosyl donors

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Article information

DOI
https://doi.org/10.1039/B306789K
Article type
Paper
Submitted
18 Jun 2003
Accepted
05 Aug 2003
First published
15 Aug 2003

Org. Biomol. Chem., 2003,1, 3147-3153

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Efficient synthesis of glycosylated phenazine natural products and analogs with DISAL (methyl 3,5-dinitrosalicylate) glycosyl donors

J. B. Laursen, L. Petersen, K. J. Jensen and J. Nielsen, Org. Biomol. Chem., 2003, 1, 3147 DOI: 10.1039/B306789K

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