Reaction participants Show >> << Hide
- Name help_outline (Z)-2-aminoethene-1-sulfonate Identifier CHEBI:231959 Charge -1 Formula C2H4NO3S InChIKeyhelp_outline UQFVJYBZUXFXKK-UPHRSURJSA-M SMILEShelp_outline N\C=C/S([O-])(=O)=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 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 2-oxoethane-1-sulfonamide Identifier CHEBI:231960 (CAS: 856194-12-2) help_outline Charge 0 Formula C2H5NO3S InChIKeyhelp_outline OWTUSYDFBOOMLH-UHFFFAOYSA-N SMILEShelp_outline [H]C(=O)CS(N)(=O)=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
Cross-references
| RHEA:82023 | RHEA:82024 | RHEA:82025 | RHEA:82026 | |
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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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Aminoacyl sulfonamide assembly in SB-203208 biosynthesis.
Hu Z., Awakawa T., Ma Z., Abe I.
Sulfonamide is present in many important drugs, due to its unique chemical and biological properties. In contrast, naturally occurring sulfonamides are rare, and their biosynthetic knowledge are scarce. Here we identify the biosynthetic gene cluster of sulfonamide antibiotics, altemicidin, SB-2032 ... >> More
Sulfonamide is present in many important drugs, due to its unique chemical and biological properties. In contrast, naturally occurring sulfonamides are rare, and their biosynthetic knowledge are scarce. Here we identify the biosynthetic gene cluster of sulfonamide antibiotics, altemicidin, SB-203207, and SB-203208, from Streptomyces sp. NCIMB40513. The heterologous gene expression and biochemical analyses reveal unique aminoacyl transfer reactions, including the tRNA synthetase-like enzyme SbzA-catalyzed L-isoleucine transfer and the GNAT enzyme SbzC-catalyzed β-methylphenylalanine transfer. Furthermore, we elucidate the biogenesis of 2-sulfamoylacetic acid from L-cysteine, by the collaboration of the cupin dioxygenase SbzM and the aldehyde dehydrogenase SbzJ. Remarkably, SbzM catalyzes the two-step oxidation and decarboxylation of L-cysteine, and the subsequent intramolecular amino group rearrangement leads to N-S bond formation. This detailed analysis of the aminoacyl sulfonamide antibiotics biosynthetic machineries paves the way toward investigations of sulfonamide biosynthesis and its engineering. << Less
Nat Commun 10:184-184(2019) [PubMed] [EuropePMC]
This publication is cited by 7 other entries.
Comments
RHEA:82023 part of RHEA:81871 This reaction can occur spontaneously. (Z)-2-aminoethene-1-sulfonate is unstable and undergoes an intramolecular rearrangement in which the amino group moves onto the oxidized sulfur atom, displacing an oxygen atom in the form of a water molecule and forming an SN bond. Another water molecule (not shown in the reaction) donates an oxygen atom that replaces the nitrogen at the other end of the molecule.