Enzymes
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Reaction participants Show >> << Hide
- Name help_outline (S)-phenylacetylcarbinol Identifier CHEBI:149670 (CAS: 53439-91-1) help_outline Charge 0 Formula C9H10O2 InChIKeyhelp_outline ZBFFNPODXBJBPW-SECBINFHSA-N SMILEShelp_outline C=1C=CC=CC1[C@@H](C(C)=O)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 NAD+ Identifier CHEBI:57540 (Beilstein: 3868403) help_outline Charge -1 Formula C21H26N7O14P2 InChIKeyhelp_outline BAWFJGJZGIEFAR-NNYOXOHSSA-M 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](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 1,207 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline 1-phenyl-1,2-propanedione Identifier CHEBI:63552 (CAS: 579-07-7) help_outline Charge 0 Formula C9H8O2 InChIKeyhelp_outline BVQVLAIMHVDZEL-UHFFFAOYSA-N SMILEShelp_outline CC(=O)C(=O)c1ccccc1 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 NADH Identifier CHEBI:57945 (Beilstein: 3869564) help_outline Charge -2 Formula C21H27N7O14P2 InChIKeyhelp_outline BOPGDPNILDQYTO-NNYOXOHSSA-L 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](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 1,136 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 9,836 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:64060 | RHEA:64061 | RHEA:64062 | RHEA:64063 | |
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| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
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Related reactions help_outline
More general form(s) of this reaction
Publications
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Biodegradation of Ephedrine Isomers by <i>Arthrobacter</i> sp. Strain TS-15: Discovery of Novel Ephedrine and Pseudoephedrine Dehydrogenases.
Shanati T., Ansorge-Schumacher M.B.
The Gram-positive soil bacterium <i>Arthrobacter</i> sp. strain TS-15 (DSM 32400), which is capable of metabolizing ephedrine as a sole source of carbon and energy, was isolated. According to 16S rRNA gene sequences and comparative genomic analysis, <i>Arthrobacter</i> sp. TS-15 is closely related ... >> More
The Gram-positive soil bacterium <i>Arthrobacter</i> sp. strain TS-15 (DSM 32400), which is capable of metabolizing ephedrine as a sole source of carbon and energy, was isolated. According to 16S rRNA gene sequences and comparative genomic analysis, <i>Arthrobacter</i> sp. TS-15 is closely related to <i>Arthrobacter aurescens</i> Distinct from all known physiological paths, ephedrine metabolism by <i>Arthrobacter</i> sp. TS-15 is initiated by the selective oxidation of the hydroxyl function at the α-C atom, yielding methcathinone as the primary degradation product. Rational genome mining revealed a gene cluster potentially encoding the novel pathway. Two genes from the cluster, which encoded putative short-chain dehydrogenases, were cloned and expressed in <i>Escherichia coli</i> The obtained enzymes were strictly NAD<sup>+</sup> dependent and catalyzed the oxidation of ephedrine to methcathinone. Pseudoephedrine dehydrogenase (PseDH) selectively converted (<i>S,S</i>)-(+)-pseudoephedrine and (<i>S,R</i>)-(+)-ephedrine to (<i>S</i>)- and (<i>R</i>)-methcathinone, respectively. Ephedrine dehydrogenase (EDH) exhibited strict selectivity for the oxidation of the diastereomers (<i>R</i>,<i>S</i>)-(-)-ephedrine and (<i>R</i>,<i>R</i>)-(-)-pseudoephedrine.<b>IMPORTANCE</b><i>Arthrobacter</i> sp. TS-15 is a newly isolated bacterium with the unique ability to degrade ephedrine isomers. The initiating steps of the novel metabolic pathway are described. <i>Arthrobacter</i> sp. TS-15 and its isolated ephedrine-oxidizing enzymes have potential for use in decontamination and synthetic applications. << Less
Appl Environ Microbiol 86:e02487-19(2020) [PubMed] [EuropePMC]
This publication is cited by 2 other entries.
Comments
Published in: Shanati, T., Lockie, C., Beloti, L., Grogan, G. and Ansorge-Schumacher, M.B. Two enantiocomplementary ephedrine dehydrogenases from Arthrobacter sp. TS-15 with broad substrate specificity. ACS Catal. 9 (2019) 6202–6211. DOI:10.1021/acscatal.9b00621