2.02012-07-30 14:54:47 -06002015-06-03 17:20:49 -0600ECMDB21182M2MDB0015916-Hydroxymethyl-dihydropterin pyrophosphate6-hydroxymethyl-dihydropterin pyrophosphate is a member of the chemical class known as Pterins and Derivatives. These are polycyclic aromatic compounds containing a pterin moeity, which consist of a pteridine ring bearing a ketone and an amine group to form 2-aminopteridin-4(3H)-one. (2-amino-4-hydroxy-7,8-dihydropteridin-6-yl)methyl diphosphate(2-amino-4-Hydroxy-7,8-dihydropteridin-6-yl)methyl diphosphoric acid2-Amino-7,8-dihydro-4-hydroxy-6-(diphosphooxymethyl)-pteridine6-hydroxymethyl-dihydropterin pyrophosphate6-Hydroxymethyl-dihydropterin pyrophosphoric acidAHHMeDHPDPDihydropterin-CH2OH-diphosphateDihydropterin-CH2OH-diphosphoric acidDihydropterin-CH2OH-ppC7H8N5O8P2352.1146351.9848102816-({[hydroxy(phosphonooxy)phosphoryl]oxy}methyl)-2-imino-1,2,7,8-tetrahydropteridin-4-olate6-({[hydroxy(phosphonooxy)phosphoryl]oxy}methyl)-2-imino-7,8-dihydro-1H-pteridin-4-olateOP(=O)(OCC1=NC2=C(NC1)NC(=N)N=C2[O-])OP([O-])([O-])=OInChI=1S/C7H11N5O8P2/c8-7-11-5-4(6(13)12-7)10-3(1-9-5)2-19-22(17,18)20-21(14,15)16/h1-2H2,(H,17,18)(H2,14,15,16)(H4,8,9,11,12,13)/p-3FCQGJGLSOWZZON-UHFFFAOYSA-KCytosollogp-1.10logs-1.83solubility5.96e+00 g/llogp-2.6pka_strongest_acidic2.07pka_strongest_basic1.48iupac6-({[hydroxy(phosphonooxy)phosphoryl]oxy}methyl)-2-imino-1,2,7,8-tetrahydropteridin-4-olateaverage_mass352.1146mono_mass351.984810281smilesOP(=O)(OCC1=NC2=C(NC1)NC(=N)N=C2[O-])OP([O-])([O-])=OformulaC7H8N5O8P2inchiInChI=1S/C7H11N5O8P2/c8-7-11-5-4(6(13)12-7)10-3(1-9-5)2-19-22(17,18)20-21(14,15)16/h1-2H2,(H,17,18)(H2,14,15,16)(H4,8,9,11,12,13)/p-3inchikeyFCQGJGLSOWZZON-UHFFFAOYSA-Kpolar_surface_area214.64refractivity98.72polarizability26.84rotatable_bond_count5acceptor_count11donor_count4physiological_charge-2formal_charge-3Folate biosynthesisThe biosynthesis of folic acid begins with a product of purine nucleotides de novo biosynthesis pathway, GTP. This compound is involved in a reaction with water through a GTP cyclohydrolase 1 protein complex, resulting in a hydrogen ion, formic acid and 7,8-dihydroneopterin 3-triphosphate. The latter compound is dephosphatased through a dihydroneopterin triphosphate pyrophosphohydrolase resulting in the release of a pyrophosphate, hydrogen ion and 7,8-dihydroneopterin 3-phosphate. The latter compound reacts with water spontaneously resulting in the release of a phosphate and a 7,8 -dihydroneopterin. This compound reacts with a dihydroneopterin aldolase, releasing a glycoaldehyde and 6-hydroxymethyl-7,9-dihydropterin. The latter compound is phosphorylated with a ATP-driven 6-hydroxymethyl-7,8-dihydropterin pyrophosphokinase resulting in a (2-amino-4-hydroxy-7,8-dihydropteridin-6-yl)methyl diphosphate.
Chorismate is metabolized by reacting with L-glutamine through a 4-amino-4-deoxychorismate synthase resulting in L-glutamic acid and 4-amino-4-deoxychorismate. The latter compound then reacts through an aminodeoxychorismate lyase resulting in pyruvic acid,hydrogen ion and p-aminobenzoic acid.
(2-amino-4-hydroxy-7,8-dihydropteridin-6-yl)methyl diphosphate and p-aminobenzoic acid react through a dihydropteroate synthase resulting in pyrophosphate and 7,8-dihydropteroic acid. This compound reacts with L-glutamic acid through an ATP driven bifunctional folylpolyglutamate synthetase / dihydrofolate synthetase resulting in a 7,8-dihydrofolate monoglutamate. This compound is reduced through an NADPH mediated dihydrofolate reductase resulting in a tetrahydrofate.
This product goes on to a one carbon pool by folate pathway.
PW000908ec00790MetabolicGTP degradationGTP, produced in the nucleotide de novo biosyntheis pathway, interacts with a water molecule through a GTP cyclohydrolase resulting in a formate, hydrogen ion and a 7,8-dihydroneopterin 3'-triphosphate. The latter compound interacts with a water molecule through a dihydroneopterin triphosphate pyrophosphohydrolase resulting in the release of a pyrophosphate, a hydrogen ion and a 7,8-dihydroneopterin 3'-phosphate. The latter compound interacts with water spontaneously resulting in the release of a phosphate and a 7,8 dihydroneopterin. The latter compound interacts with a dihydroneopterin aldolase resulting in the release of a glycolaldehyde and a 6-hydroxymethyl-7,8-dihydropterin. This compound then is then diphosphorylated by reacting with a ATP driven 6-hydroxymethyl-7,8-dihydropterin pyrophosphokinase resulting in the release of a hydrogen ion, an AMP and 6-hydroxymethyl-7,8-dihydropterin diphosphate.
GTP interacts with a cyclic pyranopterin monophosphate synthase resulting in the release of a diphosphate and a cyclic pyranopterin phosphate. The latter compound interacts with a thiocarboxylated small subunit of molybdopterin synthase (a protein) and a water molecule through a molybdopterin synthase resulting in the release of 4 hydrogen ions, 2 small subunits of molybdopterin synthase and a molybdopterin. The molybdopterin interacts with an ATP and a hydrogen ion through a molybdopterin adenylyltransferase resulting in the release of a diphosphate and a molybdopterin adenine dinucleotide.PW001888Metabolic6-hydroxymethyl-dihydropterin diphosphate biosynthesis IPWY-6147tetrahydrofolate biosynthesisPWY-6614Specdb::MsMs27800Specdb::MsMs27801Specdb::MsMs27802Specdb::MsMs34358Specdb::MsMs34359Specdb::MsMs343602524407424784870C0480757602DIHYDROPTERIN-CH2OH-PPKeseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590.21097882Dihydropteroate synthaseP0AC13DHPS_ECOLIfolPhttp://ecmdb.ca/proteins/P0AC13.xml2-amino-4-hydroxy-6-hydroxymethyldihydropteridine pyrophosphokinaseP26281HPPK_ECOLIfolKhttp://ecmdb.ca/proteins/P26281.xml6-Hydroxymethyl dihydropterin + Adenosine triphosphate > 6-Hydroxymethyl-dihydropterin pyrophosphate + Adenosine monophosphate + Hydrogen ionH2PTERIDINEPYROPHOSPHOKIN-RXNp-Aminobenzoic acid + 6-Hydroxymethyl-dihydropterin pyrophosphate > 7,8-Dihydropteroic acid + PyrophosphateH2PTEROATESYNTH-RXN6-Hydroxymethyl-dihydropterin pyrophosphate + p-Aminobenzoic acid > Pyrophosphate + 7,8-Dihydropteroic acidPW_R003401