A New Micromonospora-Produced Macrolide Antibiotic, Rosamicin

Wagman, G. H.; Waitz, J. A.; Marquez, Joseph A.; Murawski, A.; Oden, Edwin M.; Testa, R. T.; Weinstein, Marvin

doi:10.7164/antibiotics.25.641

Cited by 83 publications

(36 citation statements)

References 2 publications

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“…Rosamicin is a new macrolide antibiotic produced by Micromonospora rosaria (8). It shares certain chemical and biological characteristics with erythromycin (8,9).…”

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confidence: 99%

Rosamicin: Evaluation In Vitro and Comparison with Erythromycin and Lincomycin

1974

Antimicrob Agents Chemother

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Rosamicin is a new. macrolide antibiotic produced by Micromonospora rosaria. It shares certain chemical and biological characteristics with erythromycin. Activity against gram-positive strains was assayed by broth dilution and compared to that of erythromycin and lincomycin. Rosamicin was bacteriostatic and inhibited most strains of Staphylococcus aureus, Staphylococcus epidermidis, enterococci, viridans streptococci, and group A streptococci in concentrations of 0.02 to 4.0 ,g/ml. Results were similar for erythromycin and for lincomycin (excluding enterococci). Cross-resistance of gram-positive organismsto these three antimicrobial agents was incomplete. Rosamicin was more active than erythromycin against Enterobacteriaceae and Pseudomonas at pH 7.2. Alkalinization of the medium enhanced the activity of both rosamicin and erythromycin; however, rosamicin was still more active than erythromycin against all gram-negative strains at pH 7.6 and 8.0. In view of the high degree of in vitro activity of rosamicin against gram-positive organisms, lack of complete cross-resistance with erythromycin and lincomycin, and the greater activity of rosamicin than erythromycin against gram-negative organisms, further investigation of this macrolide is warranted.

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“…Rosamicin is a new macrolide antibiotic produced by Micromonospora rosaria (8). It shares certain chemical and biological characteristics with erythromycin (8,9).…”

mentioning

confidence: 99%

Rosamicin: Evaluation In Vitro and Comparison with Erythromycin and Lincomycin

1974

Antimicrob Agents Chemother

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“…M. rosaria NRRL 3718 and its Ade auxotroph were maintained in lyophilized vials and used throughout this study. This strain is producer of macrolide antibiotic rosamicin (13 Enrichment of auxotrophs by ampicillin treatment. For the characterization of auxotrophs, M40 media supplemented with amino acids (30 ,ug/ml), adenine and uracil (10 ,ug/ml), and vitamins (0.1 ,ug/ml) were used.…”

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confidence: 99%

Mutagenesis of Micromonospora Rosaria Using Protoplasts and Mycelial Fragments

Ryu¹,

Kim²,

Cho³

et al. 1983

Protoplasts 1983

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“…2 Rosamicin (that is rosaramicin; Figure 1) is a 16-membered macrolide antibiotic produced by Micromonospora rosaria IFO13697 (that is NRRL 3718). 3 It contains a branched lactone and deoxyhexose sugar D-desosamine at the C-5 position. The engineered strain M. rosaria TPMA0001 carries genes involved in the D-mycinose biosynthetic pathway of Micromonospora griseorubida A11725, namely, mycCI, mycCII, mycD, mycE, mycF, mydH and mydI; this engineered strain was found to produce a mycinosyl rosamicin derivative IZI.…”

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Isolation and characterization of 23-O-mycinosyl-20-dihydro-rosamicin: a new rosamicin analogue derived from engineered Micromonospora rosaria

Anzai

Sakai

et al. 2010

J Antibiot

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Macrolides, including some of the most important antibiotics clinically used, contain deoxysugars attached to an aglycone core. These sugars often impart specific biological activity to the molecule or enhance this activity. Many genes involved in the biosynthesis of macrolide antibiotics have been cloned and sequenced; in addition, the functions of many proteins encoded by macrolide biosynthetic genes have been elucidated. With this information and experimental results, manipulation of the polyketide synthase and deoxysugar biosynthetic pathways to create novel macrolide antibiotics has become possible. 1 Therefore, a combined approach that uses genes involved in the biosynthesis of macrolactone rings and deoxysugars, and in the glycosylation of macrolactone rings has been used to modify the macrolide structure. 2 Rosamicin (that is rosaramicin; Figure 1) is a 16-membered macrolide antibiotic produced by Micromonospora rosaria IFO13697 (that is NRRL 3718). 3 It contains a branched lactone and deoxyhexose sugar D-desosamine at the C-5 position. The engineered strain M. rosaria TPMA0001 carries genes involved in the D-mycinose biosynthetic pathway of Micromonospora griseorubida A11725, namely, mycCI, mycCII, mycD, mycE, mycF, mydH and mydI; this engineered strain was found to produce a mycinosyl rosamicin derivative IZI. 4 M. griseorubida A11725 produces the 16-membered macrolide antibiotic mycinamicin II, which comprises a branched lactone and two different deoxyhexose sugars-D-desosamine and D-mycinose-at the C-5 and C-21 positions, respectively. All the genes involved in D-mycinose biosynthesis lie on the mycinamicin biosynthetic gene cluster. 5 The functions of these gene products have been elucidated through chemical, genetic and enzymatic analyses. The genes mycCI and mycCII encode a cytochrome P450 enzyme and ferredoxin, respectively, which function in combination with ferredoxin reductase to mediate the hydroxylation of mycinamicin VIII at the C-21 methyl group. On completion of this hydroxylation reaction, MycD transfers 6-deoxy-D-allose to the C-21 hydroxyl group by using dTDP-6-deoxy-D-allose as a substrate; dTDP-6-deoxy-D-allose is synthesized from dTDP-4-keto and 6-deoxy-D-glucose by MydH and MydI. The methyltransferases MycE and MycF convert the resulting compound mycinamicin VI to mycinamicin IV, which has D-mycinose attached at the C-21 position. In particular, we have recently elucidated the biochemical functions of MycCI, MycCII, MycE and MycF by using the purified form of these proteins, which were overexpressed in Escherichia coli. 6,7 In our earlier study, when EtOAc extracts obtained from culture broths of the wild-strain M. rosaria IFO13697 and the engineered strain M. rosaria TPMA0001 were compared using HPLC, two additional peaks-IZI and IZII-appeared in the chromatogram (at 285 nm) of the extract from the engineered strain. IZI was identified as a mycinosyl rosamicin derivative, 23-O-mycinosyl-20-deoxo-20-dihydro-12,13-deepoxyrosamicin. 4 Moreover, our detailed studies showed that anoth...

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A New Micromonospora-Produced Macrolide Antibiotic, Rosamicin

Cited by 83 publications

References 2 publications

Rosamicin: Evaluation In Vitro and Comparison with Erythromycin and Lincomycin

Rosamicin: Evaluation In Vitro and Comparison with Erythromycin and Lincomycin

Mutagenesis of Micromonospora Rosaria Using Protoplasts and Mycelial Fragments

Isolation and characterization of 23-O-mycinosyl-20-dihydro-rosamicin: a new rosamicin analogue derived from engineered Micromonospora rosaria

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