Reaction participants Show >> << Hide
- Name help_outline dTDP-N-hydroxy-β-L-evernosamine Identifier CHEBI:77143 Charge -2 Formula C18H29N3O14P2 InChIKeyhelp_outline SNTNNQMUKUWPMM-JGQKHYKVSA-L SMILEShelp_outline CO[C@H]1[C@H](C)O[C@@H](C[C@]1(C)NO)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 2 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline NADPH Identifier CHEBI:57783 (Beilstein: 10411862) help_outline Charge -4 Formula C21H26N7O17P3 InChIKeyhelp_outline ACFIXJIJDZMPPO-NNYOXOHSSA-J SMILEShelp_outline NC(=O)C1=CN(C=CC1)[C@@H]1O[C@H](COP([O-])(=O)OP([O-])(=O)OC[C@H]2O[C@H]([C@H](OP([O-])([O-])=O)[C@@H]2O)n2cnc3c(N)ncnc23)[C@@H](O)[C@H]1O 2D coordinates Mol file for the small molecule Search links Involved in 1,329 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline O2 Identifier CHEBI:15379 (CAS: 7782-44-7) help_outline Charge 0 Formula O2 InChIKeyhelp_outline MYMOFIZGZYHOMD-UHFFFAOYSA-N SMILEShelp_outline O=O 2D coordinates Mol file for the small molecule Search links Involved in 2,851 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 9,932 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline dTDP-2,3,6-trideoxy-3-C-methyl-4-O-methyl-3-nitroso-β-L-arabino-hexopyranose Identifier CHEBI:77142 Charge -2 Formula C18H27N3O14P2 InChIKeyhelp_outline IKOVYVWEGRIBDT-JGQKHYKVSA-L SMILEShelp_outline CO[C@H]1[C@H](C)O[C@@H](C[C@]1(C)N=O)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 3 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline NADP+ Identifier CHEBI:58349 Charge -3 Formula C21H25N7O17P3 InChIKeyhelp_outline XJLXINKUBYWONI-NNYOXOHSSA-K SMILEShelp_outline NC(=O)c1ccc[n+](c1)[C@@H]1O[C@H](COP([O-])(=O)OP([O-])(=O)OC[C@H]2O[C@H]([C@H](OP([O-])([O-])=O)[C@@H]2O)n2cnc3c(N)ncnc23)[C@@H](O)[C@H]1O 2D coordinates Mol file for the small molecule Search links Involved in 1,335 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline H2O Identifier CHEBI:15377 (CAS: 7732-18-5) help_outline Charge 0 Formula H2O InChIKeyhelp_outline XLYOFNOQVPJJNP-UHFFFAOYSA-N SMILEShelp_outline [H]O[H] 2D coordinates Mol file for the small molecule Search links Involved in 6,485 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:40563 | RHEA:40564 | RHEA:40565 | RHEA:40566 | |
|---|---|---|---|---|
| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
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Publications
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A unifying nitrososynthase involved in nitrosugar biosynthesis.
Hu Y., Al-Mestarihi A., Grimes C.L., Kahne D., Bachmann B.O.
Herein we describe the cloning, functional expression and initial characterization of ORF36 from Micromonospora carbonacae var. africana and rubN8 from Streptomyces achromogenes var. rubradiris. The purified enzymes play the same role, the double-oxidation of TDP-evernosamine to TDP-evernitrosose ... >> More
Herein we describe the cloning, functional expression and initial characterization of ORF36 from Micromonospora carbonacae var. africana and rubN8 from Streptomyces achromogenes var. rubradiris. The purified enzymes play the same role, the double-oxidation of TDP-evernosamine to TDP-evernitrosose in the everninomycin and rubradirin pathways, respectively. << Less
J. Am. Chem. Soc. 130:15756-15757(2008) [PubMed] [EuropePMC]
This publication is cited by 3 other entries.
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Structure and mechanism of ORF36, an amino sugar oxidizing enzyme in everninomicin biosynthesis.
Vey J.L., Al-Mestarihi A., Hu Y., Funk M.A., Bachmann B.O., Iverson T.M.
Everninomicin is a highly modified octasaccharide that belongs to the orthosomycin family of antibiotics and possesses potent Gram-positive antibiotic activity, including broad-spectrum efficacy against multidrug resistant enterococci and Staphylococcus aureus. Among its distinctive structural fea ... >> More
Everninomicin is a highly modified octasaccharide that belongs to the orthosomycin family of antibiotics and possesses potent Gram-positive antibiotic activity, including broad-spectrum efficacy against multidrug resistant enterococci and Staphylococcus aureus. Among its distinctive structural features is a nitro sugar, l-evernitrose, analogues of which decorate a variety of natural products. Recently, we identified a nitrososynthase enzyme encoded by orf36 from Micromonospora carbonacea var. africana that mediates the flavin-dependent double oxidation of synthetically generated thymidine diphosphate (TDP)-l-epi-vancosamine to the corresponding nitroso sugar. Herein, we utilize a five-enzyme in vitro pathway both to verify that ORF36 catalyzes oxidation of biogenic TDP-l-epi-vancosamine and to determine whether ORF36 exhibits catalytic competence for any of its biosynthetic progenitors, which are candidate substrates for nitrososynthases in vivo. Progenitors solely undergo single-oxidation reactions and terminate in the hydroxylamine oxidation state. Performing the in vitro reactions in the presence of (18)O(2) establishes that molecular oxygen, rather than oxygen from water, is incorporated into ORF36-generated intermediates and products and identifies an off-pathway product that correlates with the oxidation product of a progenitor substrate. The 3.15 Å resolution X-ray crystal structure of ORF36 reveals a tetrameric enzyme that shares a fold with acyl-CoA dehydrogenases and class D flavin-containing monooxygenases, including the nitrososynthase KijD3. However, ORF36 and KijD3 have unusually open active sites in comparison to these related enzymes. Taken together, these studies map substrate determinants and allow the proposal of a minimal monooxygenase mechanism for amino sugar oxidation by ORF36. << Less
Biochemistry 49:9306-9317(2010) [PubMed] [EuropePMC]
This publication is cited by 3 other entries.
Comments
RHEA:40563 part of RHEA:40555