Reaction participants Show >> << Hide
- Name help_outline (7,8-dihydropterin-6-yl)methyl diphosphate Identifier CHEBI:72950 Charge -3 Formula C7H8N5O8P2 InChIKeyhelp_outline FCQGJGLSOWZZON-UHFFFAOYSA-K SMILEShelp_outline Nc1nc2NCC(COP([O-])(=O)OP([O-])([O-])=O)=Nc2c(=O)[nH]1 2D coordinates Mol file for the small molecule Search links Involved in 4 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline 4-aminosalicylate Identifier CHEBI:137598 Charge -1 Formula C7H6NO3 InChIKeyhelp_outline WUBBRNOQWQTFEX-UHFFFAOYSA-M SMILEShelp_outline C1=C(N)C=C(O)C(C([O-])=O)=C1 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 2-hydroxy-7,8-dihydropteroate Identifier CHEBI:137600 Charge -1 Formula C14H13N6O4 InChIKeyhelp_outline GIQHIMWSWCCNJG-UHFFFAOYSA-M SMILEShelp_outline C12=C(NCC(=N1)CNC3=CC=C(C([O-])=O)C(=C3)O)N=C(N)NC2=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 diphosphate Identifier CHEBI:33019 (Beilstein: 185088) help_outline Charge -3 Formula HO7P2 InChIKeyhelp_outline XPPKVPWEQAFLFU-UHFFFAOYSA-K SMILEShelp_outline OP([O-])(=O)OP([O-])([O-])=O 2D coordinates Mol file for the small molecule Search links Involved in 1,129 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:53732 | RHEA:53733 | RHEA:53734 | RHEA:53735 | |
|---|---|---|---|---|
| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
| UniProtKB help_outline |
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Publications
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Para-aminosalicylic acid acts as an alternative substrate of folate metabolism in Mycobacterium tuberculosis.
Chakraborty S., Gruber T., Barry C.E. III, Boshoff H.I., Rhee K.Y.
Folate biosynthesis is an established anti-infective target, and the antifolate para-aminosalicylic acid (PAS) was one of the first anti-infectives introduced into clinical practice on the basis of target-based drug discovery. Fifty years later, PAS continues to be used to treat tuberculosis. PAS ... >> More
Folate biosynthesis is an established anti-infective target, and the antifolate para-aminosalicylic acid (PAS) was one of the first anti-infectives introduced into clinical practice on the basis of target-based drug discovery. Fifty years later, PAS continues to be used to treat tuberculosis. PAS is assumed to inhibit dihydropteroate synthase (DHPS) in Mycobacterium tuberculosis by mimicking the substrate p-aminobenzoate (PABA). However, we found that sulfonamide inhibitors of DHPS inhibited growth of M. tuberculosis only weakly because of their intracellular metabolism. In contrast, PAS served as a replacement substrate for DHPS. Products of PAS metabolism at this and subsequent steps in folate metabolism inhibited those enzymes, competing with their substrates. PAS is thus a prodrug that blocks growth of M. tuberculosis when its active forms are generated by enzymes in the pathway they poison. << Less
Science 339:88-91(2013) [PubMed] [EuropePMC]
This publication is cited by 1 other entry.