Disease relevance of Deoxystreptamine

• Dialyzed extracts of the gentamicin producer Micromonospora purpurea catalyze reactions which represent transaminations proposed for 2-deoxystreptamine biosynthesis [1].
• Effect of tobramycin on protein synthesis in 2-deoxystreptamine aminoglycoside-resistant clinical isolates of Haemophilus influenzae [2].
• An [3H]azidobenzyl derivative of tobramycin, a 4,6-disubstituted 2-deoxystreptamine aminoglycoside, has been synthesized, and its ability to label Escherichia coli 70-S ribosomes under photoactivation has been studied [3].
• Biosynthesis of 2-deoxystreptamine by three crucial enzymes in Streptomyces fradiae NBRC 12773 [4].

High impact information on Deoxystreptamine

• A comparative study of inhibition by different 2-deoxystreptamine analogues reveals structural features of the aminoglycoside antibiotics required for their interaction and effect on group I introns [5].
• Substitution of the C-1 atom in the 2-deoxystreptamine moiety of gentamicin C2, a broad-spectrum aminoglycoside antibiotic, by an axial hydroxymethyl group has been reported to confer protection against most clinically important bacterial enzymes inactivating aminoglycosides, while simultaneously reducing the nephrotoxic potential of this drug [6].
• The appearance of the enzyme in late-log phase, coupled with its narrow substrate specificity, indicates that it participates predominantly in 2-deoxystreptamine biosynthesis rather than in general metabolism [1].
• Chromatographic analysis of fragments from the acid hydrolysis of these derivatives showed that the preferred site of acylation was in the 2-deoxystreptamine unit of the aminoglycosides [7].
• Hygromycin B, which is a monosubstituted 2-deoxystreptamine-containing aminoglycoside, potently inhibited the elongation of nascent chains during the translation of polysomes [8].

Chemical compound and disease context of Deoxystreptamine

• Production of antibiotic SU-2 complex by a 2-deoxystreptamine idiotroph of Micromonospora sagamiensis [9].
• Confirmation of in vitro synthesis of 2-deoxy-scyllo-inosose, the earliest intermediate in the biosynthesis of 2-deoxystreptamine, using cell free preparations of Streptomyces fradiae [10].
• Isolation and characterisation of an aminoglycoside phosphotransferase from neomycin-producing Micromonospora chalcea; comparison with that of Streptomyces fradiae and other producers of 4,6-disubstituted 2-deoxystreptamine antibiotics [11].
• Utilizing a mutant of Micromonospora inyoensis which requires the addition of 2-deoxystreptamine for sisomicin production, the bioconversion of 2-deoxstreptamine containing pseudodisaccharides and pseudotrisaccharides into sisomicin was demonstrated [12].
• A mutant of Micromonospora purpurea, which produces the gentamicin complex only when 2-deoxystreptamine is added to the fermentation medium, produces a new antibiotic complex, 2-hydroxygentamicin, when streptamine or 2,4,6/3,5-pentahydroxycyclohexanone is added to the fermentation medium [13].

Biological context of Deoxystreptamine

• A part of the new biosynthetic gene cluster for 2-deoxystreptamine-containing antibiotics was identified from Streptoalloteichus hindustanus [14].
• The syntheses include four key steps, that is, transformation of 2-deoxystreptamine moiety of lividamine to 4-N,3-O-didemethyl-2-deoxyfortamine, selective 4-N-methylation of the new aminocyclitol moiety, selective attachment of a glycyl residue to the methylamino group at C-4 and selective amination at C-6' [15].

Anatomical context of Deoxystreptamine

• The anomeric aminoglycosides, RU 21886 and RU 23468, which both have a 2-deoxystreptamine residue, stabilize 70S ribosomes to similar extents at low magnesium ion concentrations [16].

Associations of Deoxystreptamine with other chemical compounds

• In an attempt to obtain genetic markers, a number of useful Saccharomyces sp. strains and some amylolytic Schwanniomyces sp. strains were tested for their susceptibility to the antibiotic Geneticin G418 , a 2-deoxystreptamine reported to be active against bacteria, yeasts, and plant and animal cells [17].
• Crystallization and X-ray analysis of 2-deoxy-scyllo-inosose synthase, the key enzyme in the biosynthesis of 2-deoxystreptamine-containing aminoglycoside antibiotics [18].

References