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2.5.1.15: dihydropteroate synthase

This is an abbreviated version!
For detailed information about dihydropteroate synthase, go to the full flat file.

Word Map on EC 2.5.1.15

Reaction

(7,8-dihydropterin-6-yl)methyl diphosphate
+
4-Aminobenzoate
=
diphosphate
 +
7,8-dihydropteroate

Synonyms

6-hydroxymethyl-7,8-dihydropterin pyrophosphokinase-dihydropteroate synthase, 6-hydroxymethyl-7,8-dihydropterin-pyrophosphokinase-dihydropteroate synthase, 6-hydroxymethyl-7,8-dihydropteroate synthase, 7,8-dihydropteroate synthase, 7,8-dihydropteroate synthetase, 7,8-dihydropteroic acid synthetase, BCG3672c, DHP synthase, DHPS, DHPS-HPPK, DHPS/DHPR, dihydroneopterin aldolase-dihydropterin pyrophosphokinase-dihydropteroate synthase, dihydropteroate diphosphorylase, dihydropteroate synthase, dihydropteroate synthase/hydroxymethyldihydropterin pyrophosphokinase, dihydropteroate synthetase, dihydropteroic synthetase, FolP, folP1, folP2, HPPK-DHPS, hydroxymethyldihydropterin pyrophosphokinase-dihydropteroate synthase, MbDHPS, MtDHPS, Mycobacterium tuberculosis dihydropteroate synthase, PfDHPS, pfPPK-DHPS, PPPK-DHPS, putative dihydropteroate synthase ortholog, pvdhps, PvHPPK-DHPS, PVX_123230, Rv1207, synthase, dihydropteroate

ECTree

     2 Transferases
         2.5 Transferring alkyl or aryl groups, other than methyl groups
             2.5.1 Transferring alkyl or aryl groups, other than methyl groups (only sub-subclass identified to date)
                2.5.1.15 dihydropteroate synthase

Inhibitors

Inhibitors on EC 2.5.1.15 - dihydropteroate synthase

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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(7-amino-1-methyl-4,5-dioxo-1,4,5,6-tetrahydropyrimido[4,5-c]pyridazin-3-yl)acetic acid
-
-
(7-amino-4,5-dioxo-1,4,5,6-tetrahydropyrimido[4,5-c]pyridazin-3-yl)acetic acid
-
-
(E)-2-cyano-N-(4-[[(3,4-dimethylisoxazol-5-yl)amino]sulfonyl]phenyl)-3-(ethylamino)-3-(2',3',4',6'-tetra-O-acetyl-beta-D-glucopyranosylthio)acrylamide
(E)-2-cyano-N-(4-[[(3,4-dimethylisoxazol-5-yl)amino]sulfonyl]phenyl)-3-(ethylamino)-3-(ethylthio)-acrylamide
(E)-2-cyano-N-(4-[[(3,4-dimethylisoxazol-5-yl)amino]sulfonyl]phenyl)-3-(ethylamino)-3-mercapto-acrylamide
(E)-2-cyano-N-(4-[[(3,4-dimethylisoxazol-5-yl)amino]sulfonyl]phenyl)-3-(methylamino)-3-(2',3',4',6'-tetra-O-acetyl-beta-D-glucopyranosylthio)acrylamide
(E)-2-cyano-N-(4-[[(3,4-dimethylisoxazol-5-yl)amino]sulfonyl]phenyl)-3-mercapto-3-(methylamino)acrylamide
(E)-3-(allylamino)-2-cyano-N-(4-[[(3,4-dimethylisoxazol-5-yl) amino]sulfonyl]phenyl)-3-(2',3',4',6'-tetra-O-acetyl-beta-D-galactopyranosylthio)acrylamide
(E)-3-(allylamino)-2-cyano-N-(4-[[(3,4-dimethylisoxazol-5-yl)amino]sulfonyl]phenyl)-3-(2',3',4',6'-tetra-O-acetyl-beta-D-galactopyranosylthio)acrylamide
-
-
(E)-3-(allylamino)-2-cyano-N-(4-[[(3,4-dimethylisoxazol-5-yl)amino]sulfonyl]phenyl)-3-(2',3',4',6'-tetra-O-acetyl-beta-D-glucopyranosylthio)acrylamide
(E)-3-(allylamino)-2-cyano-N-(4-[[(3,4-dimethylisoxazol-5-yl)amino]sulfonyl]phenyl)-3-(ethylthio)-acrylamide
2-(2-amino-6-oxo-6,9-dihydro-1H-purin-8-yl)-N,N-diethylacetamide
-
2-(2-amino-6-oxo-6,9-dihydro-1H-purin-8-yl)-N,N-dimethylacetamide
-
2-(2-amino-6-oxo-6,9-dihydro-1H-purin-8-yl)-N-(2-methylpropyl)acetamide
-
2-(2-amino-6-oxo-6,9-dihydro-1H-purin-8-yl)-N-(3-methylbenzyl)acetamide
-
2-(2-amino-6-oxo-6,9-dihydro-1H-purin-8-yl)-N-butylacetamide
-
2-(2-amino-6-oxo-6,9-dihydro-1H-purin-8-yl)-N-cyclohexylacetamide
-
2-(2-amino-6-oxo-6,9-dihydro-1H-purin-8-yl)-N-cyclopropylacetamide
-
2-(2-amino-6-oxo-6,9-dihydro-1H-purin-8-yl)-N-ethyl-N-methylpropanamide
-
2-(2-amino-6-oxo-6,9-dihydro-1H-purin-8-yl)-N-methylacetamide
-
2-(2-amino-6-oxo-6,9-dihydro-1H-purin-8-yl)-N-phenylacetamide
-
2-(2-amino-6-oxo-6,9-dihydro-1H-purin-8-yl)-N-tert-butylacetamide
-
2-(7-amino-1-methyl-4,5-dioxo-1,4,5,6-tetrahydropyrimido[4,5-c]pyridazin-3-yl)propanoate
-
binding structure, interactions with the DHPS module and the HPPK module, modeling, ovverview
2-(7-amino-1-methyl-4,5-dioxo-1,4,5,6-tetrahydropyrimido[4,5-c]pyridazin-3-yl)propanoic acid
2-(7-amino-4,5-dioxo-1,4,5,6-tetrahydropyrimido[4,5-c]pyridazin-3-yl)propanoic acid
-
-
2-amino-4-hydroxy-6-hydroxymethyl-dihydropteridine
-
-
2-amino-6-[[4-(4-aminobenzene-1-sulfonyl)anilino]methyl]pteridin-4(1H)-one
-
2-amino-8-(2-hydroxyethyl)-1,9-dihydro-6H-purin-6-one
-
2-amino-8-(2-oxopropyl)-1,9-dihydro-6H-purin-6-one
-
2-amino-8-(3-hydroxypropyl)-1,9-dihydro-6H-purin-6-one
-
2-amino-8-(benzylsulfanyl)-9-methyl-1,9-dihydro-6H-purin-6-one
-
2-amino-8-(methylsulfanyl)-1,9-dihydro-6H-purin-6-one
-
2-amino-8-(morpholin-4-yl)-1,9-dihydro-6H-purin-6-one
-
2-amino-8-(phenylethynyl)-1,9-dihydro-6H-purin-6-one
-
2-amino-8-bromo-1,9-dihydro-6H-purin-6-one
-
2-amino-8-hydroxy-1,9-dihydro-6H-purin-6-one
-
2-amino-8-hydroxy-9-methyl-1,9-dihydro-6H-purin-6-one
-
2-amino-8-methyl-1,9-dihydro-6H-purin-6-one
-
2-amino-8-[(2,3-dimethylbenzyl)sulfanyl]-1,9-dihydro-6H-purin-6-one
-
2-amino-8-[(2,4-difluorobenzyl)sulfanyl]-1,9-dihydro-6H-purin-6-one
-
2-amino-8-[(2,5-dimethylbenzyl)sulfanyl]-1,9-dihydro-6H-purin-6-one
-
2-amino-8-[(2-bromobenzyl)sulfanyl]-1,9-dihydro-6H-purin-6-one
-
2-amino-8-[(2-chlorobenzyl)sulfanyl]-1,9-dihydro-6H-purin-6-one
-
2-amino-8-[(2-fluoro-3-methylbenzyl)sulfanyl]-1,9-dihydro-6H-purin-6-one
-
2-amino-8-[(2-fluoro-5-methylbenzyl)sulfanyl]-9-methyl-1,9-dihydro-6H-purin-6-one
-
2-amino-8-[(2-fluorobenzyl)sulfanyl]-1,9-dihydro-6H-purin-6-one
-
2-amino-8-[(2-methylbenzyl)sulfanyl]-1,9-dihydro-6H-purin-6-one
-
2-amino-8-[(2-nitrobenzyl)sulfanyl]-1,9-dihydro-6H-purin-6-one
-
2-amino-8-[(3,4-difluorobenzyl)sulfanyl]-1,9-dihydro-6H-purin-6-one
-
2-amino-8-[(3,5-dimethylbenzyl)sulfanyl]-1,9-dihydro-6H-purin-6-one
-
2-amino-8-[(3-methoxybenzyl)sulfanyl]-1,9-dihydro-6H-purin-6-one
-
2-amino-8-[(3-methylbenzyl)sulfanyl]-1,9-dihydro-6H-purin-6-one
-
2-amino-8-[(4-fluoro-2-methylbenzyl)sulfanyl]-1,9-dihydro-6H-purin-6-one
-
2-amino-8-[(4-fluoro-3-methylbenzyl)sulfanyl]-1,9-dihydro-6H-purin-6-one
-
2-amino-8-[(4-fluorobenzyl)sulfanyl]-1,9-dihydro-6H-purin-6-one
-
2-amino-8-[(naphthalen-1-ylmethyl)sulfanyl]-1,9-dihydro-6H-purin-6-one
-
2-amino-8-[(naphthalen-2-ylmethyl)sulfanyl]-1,9-dihydro-6H-purin-6-one
-
2-amino-8-[(pyridin-4-ylmethyl)sulfanyl]-1,9-dihydro-6H-purin-6-one
-
2-amino-8-[2-(4-bromophenyl)-2-oxoethyl]-1,9-dihydro-6H-purin-6-one
-
2-amino-8-[2-(4-methoxyphenyl)-2-oxoethyl]-1,9-dihydro-6H-purin-6-one
-
2-amino-8-[2-(morpholin-4-yl)-2-oxoethyl]-1,9-dihydro-6H-purin-6-one
-
2-amino-8-[[(6,6-difluorocyclohexa-2,4-dien-1-yl)methyl]sulfanyl]-1,9-dihydro-6H-purin-6-one
-
2-amino-9-benzyl-8-sulfanyl-1,9-dihydro-6H-purin-6-one
-
2-amino-9-ethyl-8-sulfanyl-1,9-dihydro-6H-purin-6-one
-
2-amino-9-methyl-1,9-dihydro-6H-purin-6-one
-
2-amino-9-methyl-8-sulfanyl-1,9-dihydro-6H-purin-6-one
-
2-amino-9-phenyl-8-sulfanyl-1,9-dihydro-6H-purin-6-one
-
2-[(2-amino-6-oxo-6,9-dihydro-1H-purin-8-yl)sulfanyl]-N-(3-chlorobenzyl)acetamide
-
2-[(2-amino-9-methyl-6-oxo-6,9-dihydro-1H-purin-8-yl)sulfanyl]-N-phenylacetamide
-
2-[[(2-amino-6-oxo-6,9-dihydro-1H-purin-8-yl)sulfanyl]methyl]benzonitrile
-
3-(7-amino-1-methyl-4,5-dioxo-1,4,5,6-tetrahydropyrimido[4,5-c]pyridazin-3-yl)butanoic acid
-
-
3-(7-amino-1-methyl-4,5-dioxo-1,4,5,6-tetrahydropyrimido[4,5-c]pyridazin-3-yl)propanoic acid
-
-
3-(7-amino-4,5-dioxo-1,4,5,6-tetrahydropyrimido[4,5-c]pyridazin-3-yl)propanoic acid
-
-
3-[[(2-amino-6-oxo-6,9-dihydro-1H-purin-8-yl)sulfanyl]methyl]benzonitrile
-
4,4-Diaminodiphenyl sulfone
-
-
4-[2-[(2-amino-6-oxo-6,9-dihydro-1H-purin-8-yl)sulfanyl]ethyl]benzenesulfonamide
-
4-[[(2-amino-4-oxo-1,4-dihydropteridin-6-yl)methyl]amino]-N-(2,6-dimethoxypyrimidin-4-yl)benzene-1-sulfonamide
-
4-[[(2-amino-4-oxo-1,4-dihydropteridin-6-yl)methyl]amino]-N-(3,4-dimethyl-1,2-oxazol-5-yl)benzene-1-sulfonamide
-
4-[[(2-amino-4-oxo-1,4-dihydropteridin-6-yl)methyl]amino]-N-(5,6-dimethoxypyrimidin-4-yl)benzene-1-sulfonamide
-
4-[[(2-amino-4-oxo-1,4-dihydropteridin-6-yl)methyl]amino]-N-(5-methyl-1,2-oxazol-3-yl)benzene-1-sulfonamide
-
4-[[(2-amino-4-oxo-1,4-dihydropteridin-6-yl)methyl]amino]-N-(pyridin-2-yl)benzene-1-sulfonamide
-
4-[[(2-amino-4-oxo-1,4-dihydropteridin-6-yl)methyl]amino]-N-(pyrimidin-2-yl)benzene-1-sulfonamide
-
4-[[(2-amino-4-oxo-3,4-dihydropteridin-6-yl)methyl]amino]-N-(3,4-dimethyl-1,2-oxazol-5-yl)benzene-1-sulfonamide
5-nitro-6-methylamino-isocytosine
-
6-hydroxymethylpterin monophosphate
6HMP, competitive inhibitor, 6-hydroxymethyl-7,8-dihydropterin diphosphate analogue
6-methylamino-5-nitrosoisocytosine
-
7,8-dihydropteroate
-
-
7,8-Dihydropteroic acid
7-amino-1-methyl-4,5-dioxo-1,4,5,6-tetrahydropyrimido[4,5-c]pyridazine-3-carboxylic acid
-
-
7-amino-3-(1-carboxyethyl)-1-methyl-pyrimido (4,5-c)-pyridazine-4,5(1H,6H)-dione
8-mercaptoguanine
-
chloramphenicol
-
dapson
KD: 0.2 microM according to molecular modelling
dapsone
dihydrofolate
dihydrofolate monoglutamate
-
-
Guanidine HCl
-
0.25 M, 50% inhibition
KCl
-
above 0.4 M
N-(4-(trifluoromethyl)-benzylidene)-1-(4-(trifluoromethyl))benzylamine
N-(4-[[(2-amino-4-oxo-1,4-dihydropteridin-6-yl)methyl]amino]benzene-1-sulfonyl)acetamide
-
NaCl
-
above 0.2 M
p-Aminobenzoate
-
-
p-aminobenzoylglutamate
-
weak
p-Aminosalicylate
p-Aminosalicylic acid
phosphanilic acid
potassium 4-([(2-amino-4-oxo-3,4-dihydro-pyrido[2,3-d]pyrimidin-6-yl)-(2-phosphonoethyl)-amino]-methyl)-benzoate
-
the oxidized analogue shows significant DHPS inhibition and significant antimicrobial activity
potassium 4-([(2-amino-4-oxo-3,4-dihydro-pyrido[2,3-d]pyrimidin-6-yl)-(3-phosphonopropyl)-amino]-methyl)-benzoate
-
the oxidized analogue shows significant DHPS inhibition and significant antimicrobial activity
Pteroate
inhibition of dihydropteroate synthase activity
Pteroic acid
PTA, product analog, binds pterin- and 4-aminobenzoate-binding regions
pyrimethamine
sulfacetamide
sulfachloropyridazine
sulfachlorpyridazine
-
Sulfadiazine
sulfadimethoxine
sulfadoxine
sulfadoxine-pyrimethamine
-
Sulfaguanidine
-
-
sulfamerazine
sulfamethazine
inhibition of dihydropteroate synthase activity
sulfamethoxazole
sulfamethoxypyridazine
sulfamonomethoxine
inhibition of dihydropteroate synthase activity
sulfamoxisole
-
effective against wild-type enzyme and mutant enzymes A437G/K540E, A437G, S436F/A437G/A613S and S436F/A437G/A613T. Ineffective against A437G/A581G
-
sulfamoxole
sulfanilamide
Sulfanilic acid
-
-
sulfapyridine
sulfaquinoxaline
sulfaquinoxazoline
-
-
sulfathiazole
sulfisomidine
sulfisoxazole
sulfonamide
Sulfonamides
-
act as competitive inhibitors with respect to the 4-amino benzoic acid substrate within the DHPS enzyme active site. The 4-amino benzoic acid/sulfonamide binding site is formed close to the protein surface by flexible protein loops facilitating rapid development of sulfonamide resistance. Study of inhibitors designed to target the conserved central pterin binding site within DHPS, molecular dynamics simulation and molecular modeling, overview. Design and synthesis of transition state analogues with ability to mimic the intermediate transient carbocation by the incorporation of a basic amine at the 6-position of the pterin ring
sulfpyridine
-
effective against wild-type enzyme. Ineffective against mutants A437G, A437G/A581G, A437G/K540E, S436F/A437G/A613S and S436F/A437G/A613T
-
tert-butyl (2-amino-6-oxo-6,9-dihydro-1H-purin-8-yl)acetate
-
tert-butyl 2-(2-amino-6-oxo-6,9-dihydro-1H-purin-8-yl)propanoate
-
tetrahydrofolate monoglutamate
-
-
tetrahydrofolate-Glu
-
-
trimethoprim-sulfamethoxazole
-
trimethroprim
-
Trp-Lys
WK, highly potent with KD: 0.23 nM according to structure-based molecular modelling and docking, overlaps with pterin monophosphate and pteroic acid binding regions, highly selective for microbial DHPS compared to human pterin and folate-binding enzymes (dihydrofolate reductase, thymidylate synthase)
Urea
-
0.9 M, 50% inhibition
[(2-amino-6-oxo-6,9-dihydro-1H-purin-8-yl)sulfanyl](phenyl)acetic acid
-
[(2-amino-6-oxo-6,9-dihydro-1H-purin-8-yl)sulfanyl]acetic acid
-
[(2-amino-9-methyl-6-oxo-6,9-dihydro-1H-purin-8-yl)sulfanyl]acetic acid
-
additional information
-