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. 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.
Laursen
Jane B
JB
Department of Chemistry, The Royal Veterinary and Agricultural University DK-1871 Frederiksberg C, Denmark.
Petersen
Lars
L
Jensen
Knud J
KJ
Nielsen
John
J
D002625:Chemistry, Organic / Q000379:methods*; D002851:Chromatography, High Pressure Liquid; D006031:Glycosylation; D008956:Models, Chemical; D010619:Phenazines / Q000138:chemical synthesis* / Q000494:pharmacology; D012459:Salicylates / Q000737:chemistry*; D013302:Streptomyces / Q000378:metabolism
D010619:Phenazines; D012459:Salicylates; C027011:3,5-dinitrosalicylic acid; C036716:saphenamycin