Dihydropteroate

Dihydropteroate is an important intermediate in folate synthesis. It is a pterin created from para-aminobenzoic acid (PABA) by the enzyme dihydropteroate synthase.

Dihydropteroate
Names
IUPAC name
4-{[(2-amino-4-oxo-1,4,7,8-tetrahydropteridin-6-yl)methyl]amino}benzoic acid
Identifiers
3D model (JSmol)
1226443
ChEBI
ChemSpider
KEGG
UNII
  • InChI=1S/C14H14N6O3/c15-14-19-11-10(12(21)20-14)18-9(6-17-11)5-16-8-3-1-7(2-4-8)13(22)23/h1-4,16H,5-6H2,(H,22,23)(H4,15,17,19,20,21) Y
    Key: WBFYVDCHGVNRBH-UHFFFAOYSA-N Y
  • InChI=1/C14H14N6O3/c15-14-19-11-10(12(21)20-14)18-9(6-17-11)5-16-8-3-1-7(2-4-8)13(22)23/h1-4,16H,5-6H2,(H,22,23)(H4,15,17,19,20,21)
    Key: WBFYVDCHGVNRBH-UHFFFAOYAH
  • O=C(O)c1ccc(cc1)NCC/2=N/C=3C(=O)\N=C(/NC=3NC\2)N
  • C1C(=NC2=C(N1)NC(=NC2=O)N)CNC3=CC=C(C=C3)C(=O)O
Properties
C14H14N6O3
Molar mass 314.3 g/mol
Hazards
GHS labelling:
Danger
H300
P264, P301+P310
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Bacteriostatic agents such as sulfonamides target dihydropteroate synthetase. The effect of dihydropteroate synthetase inhibition is comparable to that of dihydrofolate reductase inhibition by trimethoprim, another bacteriostatic agent. Combinations of these two drug types, such as the combination trimethoprim/sulfamethoxazole (TMP-SMX]), are commonly used to treat recurrent urinary tract, Shigella, Salmonella, and Pneumocystis jivoreci infections.

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