Studies on a new aminoglycoside antibiotic, dactimicin II. Isolation, structure and chemical degradation.

Abstract

A new aminoglycoside antibiotic, dactimicin produced by a Dactylosporangium matsuzakiense SF-2052 has been isolated by column chromatography on a cation-exchange resin and CM-Sephadex. The structure of dactimicin was determined to be 4-amino-l,4-dideoxy-3-O-(2,6-diamino-2,3,4,6,7-pentadeoxy-L-lyxo-heptopyranosyl)-1-[(N-formimidoylglycyl)methylamino]-6-O-methyl-L-chiro-inositol.

Aminoglycosides: Activity and Resistance

“…aminoglycosides only fortimicins, made of a diaminocyclitol (fortamine) and only one aminated sugar (see Fig. 2), have been studied [fortimicins lack the functions modified by APH(3Ј), ANT(2Љ), and ANT(4Ј) and are therefore sensitive only to AAC(6Ј) and AAC(3); dactimicin, a natural derivative of fortimicin A carrying a formimidoyl substitution on the amino group of the glycyl residue (76) (Fig. 2) is protected against AAC(6Ј)-I and -II but not against the bifunctional enzyme AAC(6Ј)-APH(2Љ) (29); it remains sensitive to AAC(3)].…”

The isolation of water-soluble natural products – challenges, strategies and perspectives

“…510 Some of the latest examples of aminoglycosides discovered from bacteria cultures include boholmycin ( 153 ) from cultures of Streptomyces hygroscopicus H617-25, 511 dactimicin ( 154 ) produced in culture by Dactylosporangium matsuzakiense SF-2052 (ref. 512) and the inosamycin complex of antibiotics ( e.g. , inosamycin A, 155 ).…”

Aminoglycosides and Aminocyclitols (Other Than Streptomycin)

“…Because of the latter characteristics, ASTM antibiotics have become the latest naturally occurring AGACs of clinical promise. Because the ASTM-group AGACs first discovered, except for dactimicin (Ohba et al 1981), were isolated and purified by ion exchange chromatography using ammonia for elution of the bound antibiotic, the 2"-N-formimidoylated species were not recovered. In the 1980s new analogues were discovered and characterized as 2"-N-formimidoyl derivatives of the originally reported antibiotics; i.e., 2"-//-formimidoylASTM (=dactimicin; Hotta et al 1989a), istamycins A and B (Kondo, et al 1982) and sporaricin (Umezawa et al 1987).…”