Enzymes
| UniProtKB help_outline | 1 proteins |
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- Name help_outline dTDP-β-L-daunosamine Identifier CHEBI:85417 Charge -1 Formula C16H26N3O13P2 InChIKeyhelp_outline CEQVCLWWGAYCPR-QUTCXQLSSA-M SMILEShelp_outline C[C@@H]1O[C@@H](C[C@H]([NH3+])[C@@H]1O)OP([O-])(=O)OP([O-])(=O)OC[C@H]1O[C@H](C[C@@H]1O)n1cc(C)c(=O)[nH]c1=O 2D coordinates Mol file for the small molecule Search links Involved in 1 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline ε-rhodomycinone Identifier CHEBI:75291 (CAS: 21288-60-8) help_outline Charge 0 Formula C22H20O9 InChIKeyhelp_outline PYFOXRACBORDCT-GOSXWKPOSA-N SMILEShelp_outline CC[C@@]1(O)C[C@H](O)c2c(O)c3C(=O)c4c(O)cccc4C(=O)c3c(O)c2[C@H]1C(=O)OC 2D coordinates Mol file for the small molecule Search links Involved in 2 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline rhodomycin D Identifier CHEBI:77073 Charge 1 Formula C28H32NO11 InChIKeyhelp_outline CADJZGPRUYOSGU-QWWLYEKJSA-O SMILEShelp_outline CC[C@@]1(O)C[C@H](O[C@H]2C[C@H]([NH3+])[C@H](O)[C@H](C)O2)c2c(O)c3C(=O)c4c(O)cccc4C(=O)c3c(O)c2[C@H]1C(=O)OC 2D coordinates Mol file for the small molecule Search links Involved in 2 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline dTDP Identifier CHEBI:58369 Charge -3 Formula C10H13N2O11P2 InChIKeyhelp_outline UJLXYODCHAELLY-XLPZGREQSA-K SMILEShelp_outline Cc1cn([C@H]2C[C@H](O)[C@@H](COP([O-])(=O)OP([O-])([O-])=O)O2)c(=O)[nH]c1=O 2D coordinates Mol file for the small molecule Search links Involved in 35 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline H+ Identifier CHEBI:15378 Charge 1 Formula H InChIKeyhelp_outline GPRLSGONYQIRFK-UHFFFAOYSA-N SMILEShelp_outline [H+] 2D coordinates Mol file for the small molecule Search links Involved in 9,717 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:45760 | RHEA:45761 | RHEA:45762 | RHEA:45763 | |
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| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
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Publications
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A two-plasmid system for the glycosylation of polyketide antibiotics: bioconversion of epsilon-rhodomycinone to rhodomycin D.
Olano C., Lomovskaya N., Fonstein L., Roll J.T., Hutchinson C.R.
<h4>Background</h4>The biological activity of many microbial products requires the presence of one or more deoxysugar molecules attached to agylcone. This is especially prevalent among polyketides and is an important reason that the antitumor anthracycline antibiotics are avid DNA-binding drugs. T ... >> More
<h4>Background</h4>The biological activity of many microbial products requires the presence of one or more deoxysugar molecules attached to agylcone. This is especially prevalent among polyketides and is an important reason that the antitumor anthracycline antibiotics are avid DNA-binding drugs. The ability to make different deoxyaminosugars and attach them to the same or different aglycones in vivo would facilitate the synthesis of new anthracyclines and the quest for antitumor drugs. This is feasible using the numerous bacterial genes for deoxysugar biosynthesis that are now available.<h4>Results</h4>Production of thymidine diphospho (TDP)-L-daunosamine (dnm), the aminodeoxysugar present in the anthracycline antitumor drugs daunorubicin (DNR) and doxorubicin (DXR), and its attachment to epsilon-rhodomycinone to generate rhodomycin D has been achieved by bioconversion with a strain of Streptomyces lividans that bears two plasmids. One contained the Streptomyces peucetius dnmJVUZTQS genes plus dnmW (previously named dpsH and considered to be a polyketide cyclase gene), dnrH, which is not required for the formation of rhodomycin D, and dnrI, a regulatory gene required for expression of the dnm and drr genes. The other plasmid had genes encoding glucose-1-phosphate thymidylyltransferase and TDP-glucose-4,6-dehydratase (dnmL and dnmM, respectively, or mtmDE, their homologs from Streptomyces agrillaceus) plus the drrAB DNR/DXR resistance genes.<h4>Conclusions</h4>The high-yielding glycosylation of the aromatic polyketide epsilon-rhodomycinone using plasmid-borne deoxysugar biosynthesis genes proves that the minimal information for L-daunosamine biosynthesis and attachment in the heterologous host is encoded by the dnmLMJVUTS genes. This is a general approach to making both known and new glycosides of anthracyclines, several of which have medically important antitumor activity. << Less
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Cloning and characterization of the Streptomyces peucetius dnrQS genes encoding a daunosamine biosynthesis enzyme and a glycosyl transferase involved in daunorubicin biosynthesis.
Otten S.L., Liu X., Ferguson J., Hutchinson C.R.
The dnrQS genes from the daunorubicin producer Streptomyces peucetius were characterized by DNA sequencing, complementation analysis, and gene disruption. The dnrQ gene is required for daunosamine biosynthesis, and dnrS appears to encode a glycosyltransferase for the addition of the 2,3,6-trideoxy ... >> More
The dnrQS genes from the daunorubicin producer Streptomyces peucetius were characterized by DNA sequencing, complementation analysis, and gene disruption. The dnrQ gene is required for daunosamine biosynthesis, and dnrS appears to encode a glycosyltransferase for the addition of the 2,3,6-trideoxy-3-aminohexose, daunosamine, to epsilon-rhodomycinone. << Less