<b>The Chemistry of Bluensomycin. I.<sup>1a</sup>The Structure of Bluensidine</b>

Bannister, B.; Argoudelis, A. D.

doi:10.1021/ja00884a033

Cited by 23 publications

(3 citation statements)

References 2 publications

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“…Bluensomycin (79), isolated from Streptomyces sp., is a streptomycin derivative in which one of the guanidine functions is replaced by a carbamate (170,(182)(183)(184).…”

Section: Streptomycin and Related Antibioticsmentioning

confidence: 99%

“…Biosynthetic studies on the arphamenines showed that arginine, acetic acid and phenylalanine are well incorporated into arphamenine A, and arginine, acetic acid and tyrosine into arphamenine B (398). Further biosynthetic experiments (399,400) have shown that ~-phenylpyruvic (181), benzylmalic (182), benzylfumaric (183) and benzylsuccinic (184) acids are intermediates in the biosynthesis of arphamenine A, thus establishing its complete biogenetic pathway (Scheme 14). phenylalanine - (183) ~~ (181) ftCCOS CoA (182) ~2r rgr.~~ Two unusual arginine derivatives, fosfazinomycins A (185) and B (186), were isolated from Streptomyces lavendofoliae (401).…”

Section: Macrocyclic Lactone Antibioticsmentioning

confidence: 99%

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Some Aspects of Guanidine Secondary Metabolites

Berlinck

1995

Fortschritte Der Chemie Organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products

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“…Bluensomycin (79), isolated from Streptomyces sp., is a streptomycin derivative in which one of the guanidine functions is replaced by a carbamate (170,(182)(183)(184).…”

Section: Streptomycin and Related Antibioticsmentioning

confidence: 99%

Section: Macrocyclic Lactone Antibioticsmentioning

confidence: 99%

Some Aspects of Guanidine Secondary Metabolites

Berlinck

1995

Fortschritte Der Chemie Organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products

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“…Bluensomycin (glebomycin) (Fig 1, II) differs structurally from dihydrostreptomycin in having an O-carbamoyl group at position 1 rather than a second guanidino group (1,2,13,17), and hence it is a logical candidate for the postulated progenitor compound. Previous studies revealed that extracts of the bluensomycin producer Streptomyces hygroscopicus form glebosus ATCC 14607 (S. glebosus) catalyzed reactions C, D, F, G, and K of Fig.…”

mentioning

confidence: 99%

Possible evolutionary relationships between streptomycin and bluensomycin biosynthetic pathways: detection of novel inositol kinase and O-carbamoyltransferase activities

Walker

1990

J Bacteriol

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Bluensomycin (glebomycin) is an aminocyclitol antibiotic that differs structurally from dihydrostreptomycin in having bluensidine (lD-1-O-carbamoyl-3-guanidinodeoxy-scyllo-inositol) rather than streptidine (1,3-diguanidino-1,3-dideoxy-scyllo-inositol) as its aminocyclitol moiety. Extracts of the bluensomycin producer Streptomyces hygroscopicus form glebosus ATCC 14607 (S. glebosus) were found to have aminodeoxy-scylloinositol kinase activity but to lack 1D-1-guanidino-3-amino-1,3-dideoxy-scyllo-inositol kinase activity, showing for the first time that these two reactions in streptomycin producers must be catalyzed by different enzymes.S. glebosus extracts therefore possess the same five enzymes required for synthesis of guanidinodeoxy-scylloinositol from myo-inositol that are found in streptomycin producers but lack the next three of the four enzymes found in streptomycin producers that are required to synthesize the second guanidino group of streptidine-P.In place of a second guanidino group, S. glebosus extracts were found to catalyze a Mg2e-dependent carbamoylation of guanidinodeoxy-scyllo-inositol to form bluensidine, followed by a phosphorylation to form bluensidine-P. The novel carbamoyl-P:guanidinodeoxy-scyllo-inositol O-carbamoyltransferase and ATP:bluensidine phosphotransferase activities were not detected in streptomycin producers or in S. glebosus during its early rapid growth phase. Free bluensidine appears to be a normal intermediate in bluensomycin biosynthesis, in contrast to the case of streptomycin biosynthesis; in the latter, although exogenous streptidine can enter the pathway via streptidine-P, free streptidine is not an intermediate in the endogenous biosynthetic pathway. Comparison of the streptomycin and bluensomycin biosynthetic pathways provides a unique opportunity to evaluate those proposed mechanisms for the evolutionary acquisition of new biosynthetic capabilities that involve gene duplication and subsequent mutational changes in one member of the pair. In this model, there are at least five pairs of enzymes catalyzing analogous reactions that can be analyzed for homology at both the protein and DNA levels, including two putative pairs of inositol kinases detected in this study.Actinomycete soil bacteria have a large excess of DNA in their genomes over that required for growth and morphological differentiation. Much of this excess DNA codes for enzymes responsible for the unique biosynthetic abilities of actinomycetes, which as a group produce 70% of the known antibiotics plus numerous other idiolites (secondary metabolites). The mechanisms and selection procedures by which the diverse pathways for idiolite biosynthesis have evolved and are maintained are problems of both theoretical and practical interest. Model systems for addressing these problems must be amenable to both enzymatic and genetic analysis. The streptomycin biosynthetic pathway fulfills these two requirements for a model system (32).Enzymatic studies on biosynthesis of the streptidine moiety of dihydrostreptomycin (Fi...

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Antibiotics

1965

Biotech & Bioengineering

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The Chemistry of Bluensomycin. I.^1aThe Structure of Bluensidine

Cited by 23 publications

References 2 publications

Some Aspects of Guanidine Secondary Metabolites

Some Aspects of Guanidine Secondary Metabolites

Possible evolutionary relationships between streptomycin and bluensomycin biosynthetic pathways: detection of novel inositol kinase and O-carbamoyltransferase activities

Antibiotics

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The Chemistry of Bluensomycin. I.1aThe Structure of Bluensidine

Cited by 23 publications

References 2 publications

Some Aspects of Guanidine Secondary Metabolites

Some Aspects of Guanidine Secondary Metabolites

Possible evolutionary relationships between streptomycin and bluensomycin biosynthetic pathways: detection of novel inositol kinase and O-carbamoyltransferase activities

Antibiotics

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The Chemistry of Bluensomycin. I.^1aThe Structure of Bluensidine