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- Name help_outline Ni(II)-pyridinium-3,5-bisthiocarboxylate mononucleotide Identifier CHEBI:137373 Charge -1 Formula C12H11NNiO9PS2 InChIKeyhelp_outline GIEIRHLCPQGQDJ-WFFMJNDQSA-L SMILEShelp_outline O(C[C@H]1O[C@@H]([N+]2=CC3=C4C(=C2)C(=[S+][Ni-]4SC3=O)O)[C@@H]([C@@H]1O)O)P([O-])(=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 Ni2+ Identifier CHEBI:49786 (CAS: 14701-22-5) help_outline Charge 2 Formula Ni InChIKeyhelp_outline VEQPNABPJHWNSG-UHFFFAOYSA-N SMILEShelp_outline [Ni++] 2D coordinates Mol file for the small molecule Search links Involved in 5 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline pyridinium-3,5-bisthiocarboxylate mononucleotide Identifier CHEBI:137372 Charge -3 Formula C12H11NO9PS2 InChIKeyhelp_outline KAWCHOIDVYCQHC-ZYUZMQFOSA-K SMILEShelp_outline O(C[C@H]1O[C@@H]([N+]2=CC(=CC(=C2)C([S-])=O)C([S-])=O)[C@@H]([C@@H]1O)O)P([O-])(=O)[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
Cross-references
| RHEA:54784 | RHEA:54785 | RHEA:54786 | RHEA:54787 | |
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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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Nickel-pincer cofactor biosynthesis involves LarB-catalyzed pyridinium carboxylation and LarE-dependent sacrificial sulfur insertion.
Desguin B., Soumillion P., Hols P., Hausinger R.P.
The lactate racemase enzyme (LarA) of Lactobacillus plantarum harbors a (SCS)Ni(II) pincer complex derived from nicotinic acid. Synthesis of the enzyme-bound cofactor requires LarB, LarC, and LarE, which are widely distributed in microorganisms. The functions of the accessory proteins are unknown, ... >> More
The lactate racemase enzyme (LarA) of Lactobacillus plantarum harbors a (SCS)Ni(II) pincer complex derived from nicotinic acid. Synthesis of the enzyme-bound cofactor requires LarB, LarC, and LarE, which are widely distributed in microorganisms. The functions of the accessory proteins are unknown, but the LarB C terminus resembles aminoimidazole ribonucleotide carboxylase/mutase, LarC binds Ni and could act in Ni delivery or storage, and LarE is a putative ATP-using enzyme of the pyrophosphatase-loop superfamily. Here, we show that LarB carboxylates the pyridinium ring of nicotinic acid adenine dinucleotide (NaAD) and cleaves the phosphoanhydride bond to release AMP. The resulting biscarboxylic acid intermediate is transformed into a bisthiocarboxylic acid species by two single-turnover reactions in which sacrificial desulfurization of LarE converts its conserved Cys176 into dehydroalanine. Our results identify a previously unidentified metabolic pathway from NaAD using unprecedented carboxylase and sulfur transferase reactions to form the organic component of the (SCS)Ni(II) pincer cofactor of LarA. In species where larA is absent, this pathway could be used to generate a pincer complex in other enzymes. << Less
Proc. Natl. Acad. Sci. U.S.A. 113:5598-5603(2016) [PubMed] [EuropePMC]
This publication is cited by 9 other entries.