Dihydropteroate

Dihydropteroate is an important intermediate in folate synthesis. It is a pterin created from para-aminobenzoic acid (PABA) by the enzyme dihydropteroate synthase.[1]

Tetrahydrofolate synthesis pathway

Dihydropteroate

Names
IUPAC name 4-{[(2-amino-4-oxo-1,4,7,8-tetrahydropteridin-6-yl)methyl]amino}benzoic acid
Identifiers
CAS Number	2134-76-1^N
3D model (JSmol)	Interactive image Interactive image
Beilstein Reference	1226443
ChEBI	CHEBI:4581^Y
ChemSpider	165^Y
KEGG	C00921^N
PubChem CID	170
CompTox Dashboard (EPA)	DTXSID40175605
InChI 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
SMILES 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
Chemical formula	C14H14N6O3
Molar mass	314.3 g/mol
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.

See also

• Dihydrofolic acid

References

1. Hevener, Kirk E; Yun, Mi-Kyung; Qi, Jianjun; Kerr, Iain D; Babaoglu, Kerim; Hurdle, Julian G; Balakrishna, Kanya; White, Stephen W; Lee, Richard E (2010). "Structural Studies of Pterin-Based Inhibitors of Dihydropteroate Synthase". Journal of Medicinal Chemistry. 53 (1): 166–177. doi:10.1021/jm900861d. PMC 2804029. PMID 19899766.