carubicin and rhodomycinone

carubicin has been researched along with rhodomycinone* in 2 studies

Other Studies

2 other study(ies) available for carubicin and rhodomycinone

Article	Year
In vivo and in vitro bioconversion of epsilon-rhodomycinone glycoside to doxorubicin: functions of DauP, DauK, and DoxA. Journal of bacteriology, 1997, Volume: 179, Issue:8 We recently determined the function of the gene product of Streptomyces sp. strain C5 doxA, a cytochrome P-450-like protein, to be daunorubicin C-14 hydroxylase (M. L. Dickens and W. R. Strohl, J. Bacteriol. 178: 3389-3395, 1996). In the present study, we show that DoxA also catalyzes the hydroxylation of 13-deoxycarminomycin and 13-deoxydaunorubicin to 13-dihydrocarminomycin and 13-dihydrodaunorubicin, respectively, as well as oxidizing the 13-dihydro-anthracyclines to their respective 13-keto forms. The Streptomyces sp. strain C5 dauP gene product also was shown unequivocally to remove the carbomethoxy group of the epsilon-rhodomycinone-glycoside (rhodomycin D) to form 10-carboxy-13-deoxycarminomycin. Additionally, Streptomyces sp. strain C5 DauK was found to methylate the anthracyclines rhodomycin D, 10-carboxy-13-deoxycarminomycin, and 13-deoxy-carminomycin, at the 4-hydroxyl position, indicating a broader substrate specificity than was previously known. The products of Streptomyces sp. strain C5 doxA, dauK, and dauP were sufficient and necessary to confer on Streptomyces lividans TK24 the ability to convert rhodomycin D, the first glycoside in daunorubicin and doxorubicin biosynthesis, to doxorubicin. Topics: Anthracyclines; Bacterial Proteins; Carubicin; Cytochrome P-450 Enzyme System; Daunorubicin; Doxorubicin; Esterases; Genes, Bacterial; Hydroxylation; Methyltransferases; Models, Chemical; Multigene Family; Recombinant Fusion Proteins; Restriction Mapping; Streptomyces; Substrate Specificity	1997
8-Hydroxyanthracyclinones from epsilon-rhodomycinone. Journal of medicinal chemistry, 1980, Volume: 23, Issue:11 epsilon-Rhodomycinone was converted into 8,9-dehydro-zeta-rhodomycinone, which gave a cis diol with osmium tetroxide and a pair of epimeric epoxides with m-chloroperbenzoic acid. Acid-catalyzed opening of the epoxides gave the corresponding trans diols. In contrast, acid treatment of the trimethyl ethers of these epoxides gave predominantly a lactone and an eta-rhodomycinone derivative, with only small amounts of the diols. None of the new rhodomycinones were active against Bacillus subtilis, but 8,9-dehydro-zeta-rhodomycinone was active in the induction of lytic phage in Escherichia coli. Topics: Anthracyclines; Bacillus subtilis; Coliphages; Naphthacenes; Virus Activation	1980

Article

Year

In vivo and in vitro bioconversion of epsilon-rhodomycinone glycoside to doxorubicin: functions of DauP, DauK, and DoxA.

Journal of bacteriology, 1997, Volume: 179, Issue:8

We recently determined the function of the gene product of Streptomyces sp. strain C5 doxA, a cytochrome P-450-like protein, to be daunorubicin C-14 hydroxylase (M. L. Dickens and W. R. Strohl, J. Bacteriol. 178: 3389-3395, 1996). In the present study, we show that DoxA also catalyzes the hydroxylation of 13-deoxycarminomycin and 13-deoxydaunorubicin to 13-dihydrocarminomycin and 13-dihydrodaunorubicin, respectively, as well as oxidizing the 13-dihydro-anthracyclines to their respective 13-keto forms. The Streptomyces sp. strain C5 dauP gene product also was shown unequivocally to remove the carbomethoxy group of the epsilon-rhodomycinone-glycoside (rhodomycin D) to form 10-carboxy-13-deoxycarminomycin. Additionally, Streptomyces sp. strain C5 DauK was found to methylate the anthracyclines rhodomycin D, 10-carboxy-13-deoxycarminomycin, and 13-deoxy-carminomycin, at the 4-hydroxyl position, indicating a broader substrate specificity than was previously known. The products of Streptomyces sp. strain C5 doxA, dauK, and dauP were sufficient and necessary to confer on Streptomyces lividans TK24 the ability to convert rhodomycin D, the first glycoside in daunorubicin and doxorubicin biosynthesis, to doxorubicin.

Topics: Anthracyclines; Bacterial Proteins; Carubicin; Cytochrome P-450 Enzyme System; Daunorubicin; Doxorubicin; Esterases; Genes, Bacterial; Hydroxylation; Methyltransferases; Models, Chemical; Multigene Family; Recombinant Fusion Proteins; Restriction Mapping; Streptomyces; Substrate Specificity

1997

8-Hydroxyanthracyclinones from epsilon-rhodomycinone.

Journal of medicinal chemistry, 1980, Volume: 23, Issue:11

epsilon-Rhodomycinone was converted into 8,9-dehydro-zeta-rhodomycinone, which gave a cis diol with osmium tetroxide and a pair of epimeric epoxides with m-chloroperbenzoic acid. Acid-catalyzed opening of the epoxides gave the corresponding trans diols. In contrast, acid treatment of the trimethyl ethers of these epoxides gave predominantly a lactone and an eta-rhodomycinone derivative, with only small amounts of the diols. None of the new rhodomycinones were active against Bacillus subtilis, but 8,9-dehydro-zeta-rhodomycinone was active in the induction of lytic phage in Escherichia coli.

Topics: Anthracyclines; Bacillus subtilis; Coliphages; Naphthacenes; Virus Activation

1980