Reaction participants Show >> << Hide
- Name help_outline mithramycin DK Identifier CHEBI:81906 Charge 0 Formula C52H74O24 InChIKeyhelp_outline GXBYLUZTDNFHPE-HBTOKZPTSA-N SMILEShelp_outline [H]C1(CC2=CC3=CC(OC4OC(C)C(O)C(OC5OC(C)C(O)C(O)C5)C4)=C(C(O)=C3C(O)=C2C(=O)C1OC6OC(C)C(O)C(OC7OC(C)C(O)C(OC8OC(C)C(O)C(O)(C)C8)C7)C6)C)C(OC)C(=O)C(O)C(=O)C 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 1,365 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 10,232 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline iso-mithramycin Identifier CHEBI:234324 Charge 0 Formula C52H76O24 InChIKeyhelp_outline CFCUWKMKBJTWLW-HVYJJLEASA-N SMILEShelp_outline [H]C1(CC2=CC3=CC(OC4OC(C)C(O)C(OC5OC(C)C(O)C(O)C5)C4)=C(C(O)=C3C(O)=C2C(=O)C1OC6OC(C)C(O)C(OC7OC(C)C(O)C(OC8OC(C)C(O)C(O)(C)C8)C7)C6)C)C(OC)C(=O)C(O)C(O)C 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 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 1,372 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:85451 | RHEA:85452 | RHEA:85453 | RHEA:85454 | |
|---|---|---|---|---|
| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
| UniProtKB help_outline |
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Related reactions help_outline
More general form(s) of this reaction
Publications
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Discovery of a Cryptic Intermediate in Late Steps of Mithramycin Biosynthesis.
Wheeler R., Yu X., Hou C., Mitra P., Chen J.M., Herkules F., Ivanov D.N., Tsodikov O.V., Rohr J.
MtmOIV and MtmW catalyze the final two reactions in the mithramycin (MTM) biosynthetic pathway, the Baeyer-Villiger opening of the fourth ring of premithramycin B (PMB), creating the C3 pentyl side chain, strictly followed by reduction of the distal keto group on the new side chain. Unexpectedly t ... >> More
MtmOIV and MtmW catalyze the final two reactions in the mithramycin (MTM) biosynthetic pathway, the Baeyer-Villiger opening of the fourth ring of premithramycin B (PMB), creating the C3 pentyl side chain, strictly followed by reduction of the distal keto group on the new side chain. Unexpectedly this results in a C2 stereoisomer of mithramycin, iso-mithramycin (iso-MTM). Iso-MTM undergoes a non-enzymatic isomerization to MTM catalyzed by Mg<sup>2+</sup> ions. Crystal structures of MtmW and its complexes with co-substrate NADPH and PEG, suggest a catalytic mechanism of MtmW. The structures also show that a tetrameric assembly of this enzyme strikingly resembles the ring-shaped β subunit of a vertebrate ion channel. We show that MtmW and MtmOIV form a complex in the presence of PMB and NADPH, presumably to hand over the unstable MtmOIV product to MtmW, yielding iso-MTM, as a potential self-resistance mechanism against MTM toxicity. << Less
Angew Chem Int Ed Engl 59:826-832(2020) [PubMed] [EuropePMC]
This publication is cited by 1 other entry.