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

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. Benzoyl...

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Veröffentlicht in:	Organic & biomolecular chemistry 2003-09, Vol.1 (18), p.3147-3153
Hauptverfasser:	Laursen, Jane B, Petersen, Lars, Jensen, Knud J, Nielsen, John
Format:	Artikel
Sprache:	eng
Schlagworte:	Chemistry, Organic - methods Chromatography, High Pressure Liquid Glycosylation Models, Chemical Phenazines - chemical synthesis Phenazines - pharmacology Salicylates - chemistry Streptomyces - metabolism
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description	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.
doi_str_mv	10.1039/b306789k
format	Article
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source	Royal Society of Chemistry Journals Archive (1841-2007); MEDLINE; Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection
subjects	Chemistry, Organic - methods Chromatography, High Pressure Liquid Glycosylation Models, Chemical Phenazines - chemical synthesis Phenazines - pharmacology Salicylates - chemistry Streptomyces - metabolism
title	Efficient synthesis of glycosylated phenazine natural products and analogs with DISAL (methyl 3,5-dinitrosalicylate) glycosyl donors
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