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4.6.1.12: 2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase

This is an abbreviated version!
For detailed information about 2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase, go to the full flat file.

Word Map on EC 4.6.1.12

Reaction

2-phospho-4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol
=
2-C-methyl-D-erythritol 2,4-cyclodiphosphate
+
CMP

Synonyms

MECDP-synthase, MECPS, MCS, YgbB protein, MECDP synthase, IspDF, IspE, MEC synthase, 2C-methyl-D-erythrol-2,4-cyclodiphosphate synthase, MECS, MECP, cMEPP synthase, IspF, 2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase, YGBB, 2-methylerythritol 2,4-cyclodiphosphate synthase, 2C-methyl-D-erythritol-2,4-cyclodiphosphate synthase, ME-CPP synthase, 2C-methyl-D-erythritol 2,4-cyclodiphosphate synthase, MDS, 2-C-methyl-D-erythritol-2,4-cyclodiphosphate synthase

ECTree

     4 Lyases
         4.6 Phosphorus-oxygen lyases
             4.6.1 Phosphorus-oxygen lyases (only sub-subclass identified to date)
                4.6.1.12 2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase

Inhibitors

Inhibitors on EC 4.6.1.12 - 2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase

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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(+)-(S)-ethyl (2Z)-5-(1-benzofuran-2-yl)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
(+/-)-(2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-5,7-dimethyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylic acid
(+/-)-(2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylic acid
(+/-)-benzyl (2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
(+/-)-benzyl 6-methyl-4-(2-thienyl)-2-thioxo-1,2,3,4-tetra-hydropyrimidine-5-carboxylate
(+/-)-ethyl (2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-5-(4-methoxyphenyl)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
(+/-)-ethyl (2Z)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
(+/-)-ethyl (2Z)-2-(3,5-difluoro-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
(+/-)-ethyl (2Z)-2-(3-bromo-4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
(+/-)-ethyl (2Z)-2-(4-hydroxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
(+/-)-ethyl (2Z)-2-(4-methoxybenzylidene)-7-methyl-3-oxo-5-(2-thienyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
(+/-)-ethyl (2Z)-2-[4-(acetyloxy)-3,5-dibromobenzylidene]-5-(1-benzofuran-2-yl)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo-[3,2-a]pyrimidine-6-carboxylate
(+/-)-ethyl (2Z)-5-(1-benzofuran-2-yl)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
(+/-)-ethyl (2Z)-5-(1-benzofuran-2-yl)-2-(3,5-dichloro-4-hydroxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
(+/-)-ethyl 4-(4-methoxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylate
(-)-(R)-ethyl (2Z)-5-(1-benzofuran-2-yl)-2-(3,5-dibromo-4-hydroxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
2-amino-N-hydroxy-3-(1-H-indol-3-yl)-propionimidic acid
highest affinity of all the ligands examined, due to Zn2+-hydroxamate coordination, KD value of 0.0019 mM
4-amino-1-(3-O-phosphono-a-D-lyxofuranosyl)pyrimidin-2(1H)-one
-
4-amino-1-[(2S,3aS,4S,6R,6aR)-2-hydroxy-6-(hydroxymethyl)-2-oxidotetrahydrofuro[3,4-d][1,3,2]dioxaphosphol-4-yl]pyrimidin-2(1H)-one
KD value of 20.5 mM
4-amino-1-[(4aR,6R,7R,7aS)-2,7-dihydroxy-2-oxidotetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl]pyrimidin-2(1H)-one
KD value of 0.925 mM
5-fluorocytidine
KD value of 2.02 mM
Cidofovir
KD value of ca. 40 mM
Cytosine arabinoside monophosphate
KD value of 18.91 mM
EDTA
5 mM. Activity can be restored by the addition of Mg2+ to a concentration of 10 mM
N-([4-[(4-amino-2-oxopyrimidin-1(2H)-yl)methyl]-1-naphthyl]methyl)-4-chlorobenzamide
1 mM, 52% inhibition
N-([4-[(4-amino-2-oxopyrimidin-1(2H)-yl)methyl]-1-naphthyl]methyl)benzamide
1 mM, 59% inhibition
N-[4-[(6-aminopyridin-3-yl)amino]-3-methylbenzyl]-4-(trifluoromethyl)benzamide
1 mM, 60% inhibition
additional information
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