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

Jane B. Laursen, Lars Petersen, K.J. Jensen, John Nielsen

Research output: Contribution to journalJournal articleResearchpeer-review

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.
Original languageEnglish
JournalOrganic & Biomolecular Chemistry
Volume1
Issue number18
Pages (from-to)3147-3153
ISSN1477-0520
Publication statusPublished - 2003

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