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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2019/06/17 18:46:41」(JST)

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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

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.

References

^ 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.

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1. 尿酸腎結石症uric acid nephrolithiasis [show details]
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4. 妊娠中の葉酸補充folic acid supplementation in pregnancy [show details]
…consume some folic acid as folate is a natural component of a variety of foods, and grain products in many countries are fortified with folic acid. This topic will discuss the role of folic acid supplementation …
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… Valproic acid (2-propylpentanoic acid; VPA) is a branched-chain carboxylic acid introduced as an anti-epileptic drug in 1978 in the United States. It is used to treat partial and generalized seizures …

English Journal

Anti-folates potentiate bactericidal effects of other antimicrobial agents.

Li K, Wang XD, Yang SS, Gu J, Deng JY, Zhang XE.
The Journal of antibiotics. 2017 Mar;70(3)285-291.
Synergies between sulfonamides and other antimicrobial agents have long been reported, but the reason still remains unclear. Previously, Vilchèze et al. found that, sulfamethoxazole (SMX) could potentiate the bacterialcidal activity of isoniazid (INH) and rifampin (RIF) in Mycobacterium tuberculosi
PMID 28074051

Folate-synthesizing enzyme system as target for development of inhibitors and inhibitor combinations against Candida albicans-synthesis and biological activity of new 2,4-diaminopyrimidines and 4'-substituted 4-aminodiphenyl sulfones.

Otzen T, Wempe EG, Kunz B, Bartels R, Lehwark-Yvetot G, Hänsel W, Schaper KJ, Seydel JK.
Journal of medicinal chemistry. 2004 Jan;47(1)240-53.
The paper describes the design, synthesis, and testing of inhibitors of folate-synthesizing enzymes and of whole cell cultures of Candida albicans. The target enzymes used were dihydropteroic acid synthase (SYN) and dihydrofolate reductase (DHFR). Several series of new 2,4-diaminopyrimidines were sy
PMID 14695838

Cytotoxicity of dihydropteroate in Saccharomyces cerevisiae.

Bayly AM, Macreadie IG.
FEMS microbiology letters. 2002 Aug;213(2)189-92.
Microbes and plants synthesise folate using a unique biosynthetic pathway that is absent in animals. The end product, tetrahydrofolate, is utilised by all forms of life. In this study, an intermediate in this synthesis, dihydropteroic acid, was found to be toxic to Saccharomyces cerevisiae. Further
PMID 12167536

Japanese Journal

Nutritional requirements for folate compounds and some enzyme activities involved in the folate biosynthesis.

岩井和夫,池田雅充,藤野舜一
Ｊｏｕｒｎａｌ　ｏｆ　Ｎｕｔｒｉｔｉｏｎａｌ　Ｓｃｉｅｎｃｅ　ａｎｄ　Ｖｉｔａｍｉｎｏｌｏｇｙ 23(2), 95-100, 1977
… cerevisiae, which require essentially pteroylglutamic acid as a nutrient for growth showed no detectable dihydrofolate synthetase activity. … R, which can replace pteroylglutamic acid with pteroic acid as a nutrient for growth, had little dihydropteroate synthetase activity but showed normal dihydro-folate synthetase activity. …
NAID 130001372374

Purification and properties of the dihydrofolate synthetase from serratia indica.

池田雅充,岩井和夫
Ｊｏｕｒｎａｌ　ｏｆ　Ｎｕｔｒｉｔｉｏｎａｌ　Ｓｃｉｅｎｃｅ　ａｎｄ　Ｖｉｔａｍｉｎｏｌｏｇｙ 22(3), 235-248, 1976
… 12) responsible for catalyzing the synthesis of dihydrofolic acid from dihydropteroic acid and L-glutamic acid was purified about 130-fold from extracts of Serratia indica … γ-L-GlutamylL-glutamic acid cannot replace L-glutamic acid as the substrate. … Neither pteroic acid nor tetrahydropteroic acid can be used as the substrate. …
NAID 130001372517

Purification and properties of the dihydrofolate synthetase from pea seedlings.

岩井和夫,池田雅充
Ｊｏｕｒｎａｌ　ｏｆ　Ｎｕｔｒｉｔｉｏｎａｌ　Ｓｃｉｅｎｃｅ　ａｎｄ　Ｖｉｔａｍｉｎｏｌｏｇｙ 21(1), 7-18, 1975
… The enzyme was specific for dihydropteroic acid as the substrate. … This suggests that the product from ATP in the reaction is composed of ADP+Pi. Thus, it is proposed that this enzyme catalyzes the following reaction: Dihydropteroic acid+L-glutamic acid+ATP Mg2+ … or Rb+) Dihydrofolic acid+ADP+Pi. …
NAID 130001372699

「ジヒドロプテロイン酸」

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 ;
3D model (JSmol)	Interactive image; Interactive image;
Beilstein Reference	1226443
ChEBI	CHEBI:4581 ;
ChemSpider	165 ;
KEGG	C00921 ;
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) Key: WBFYVDCHGVNRBH-UHFFFAOYSA-N ; 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).
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	Infobox references

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英: dihydropteroate, dihydropteroic acid
関: プテリン

[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.

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dihydropteroic acid