Glutamine from Streptomyces

One example of a naturally occurring diazirine, duazomycin A (137 Scheme 11.20), has been reported, isolated in 1985 from a Streptomyces species during a screen for herbicidal compounds [196], It was fotind to inhibit de novo starch synthesis and it was suggested that this is due to direct inhibition of protein synthesis. Duazomycin A is structurally related to 6-diazo-5-oxo-L-norleucine (138), also reported as a natural product from Streptomyces [197], which acts as a glutamine antagonist and inhibits purine biosynthesis [198],... 

C5H7N3O4, Mr 173.13. Light yellow to greenish cryst., mp. 153-155°C (decomp.), [a]p +9.T (2 N HCI). A. is an antibiotic, isolated in optically active L-form, from Streptomyces species, the racemic form can be synthesized. As antagonist of glutamine it has mutagenic, bactericidal, fungicidal, and cytostatic activities. 

Nitrogen can be transferred from glutamine into many other substrates.102 Several antibiotic analogs of glutamine have been useful in studying these processes. Examples are the streptomyces antibiotics L-azaserine and 6-diazo-5-oxo-L-norleucine (DON). 

Walker, J.B., 1995, Enzymatic synthesis of aminocyclitol moieties of aminoglycoside antibiotics from inositol by Streptomyces spp. Detection of glutamine-aminocyclitol aminotransferase and diaminocyclitol aminotransferase activities in a spectinomycin producer. J. Bacteriol. 177 818-822. 

Azaserine (L-serine diazoacetate), isolated from a species of Streptomyces, is a structural analogue of glutamine... 

Nitrogen metabolism plays a critical role in the biosynthesis of the streptothricin-type antibiotic nourseothricin in Streptomyces noursei [102]. Glutamine synthetase is repressed in this organism by a high concentration of ammonium ions. After the ammonium ion is depleted from the medium, derepression of the enzyme occurs. O-aminobenzoic (anthranilic) acid stimulates nourseothricin production and has a marked effect on regulation of enzymes responsible for nitrogen metabolism [102]. 

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