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Issue 18, 2003
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Efficient synthesis of glycosylated phenazine natural products and analogs with DISAL (methyl 3,5-dinitrosalicylate) glycosyl donors

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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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Publication details

The article was received on 18 Jun 2003, accepted on 05 Aug 2003 and first published on 15 Aug 2003


Article type: Paper
DOI: 10.1039/B306789K
Citation: 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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