2.02012-05-31 14:54:13 -06002015-09-13 12:56:14 -0600ECMDB21007M2MDB001426L-AllothreonineAllothreonine is the substrate of the enzyme Serine hydroxymethyltransferase1 (SHMT, EC 2.1.2.1). SHMT uses pyridoxal 5'-phosphate (PLP) and tetrahydropteroylglutamate (H4PteGlu) as coenzymes and catalyzes the reversible interconversion of serine and glycine. In addition to these physiological reactions, SHMT also catalyzes, in the absence of H4PteGlu, the retroaldol cleavage of several 3-hydroxyamino acids, such as allothreonine. (2S,3S)-2-amino-3-hydroxybutanoate(2S,3S)-2-amino-3-hydroxybutanoic acidAllo-L-threonineD-AllothreonineL-Allo-ThreonineC4H9NO3119.1192119.058243159(2S,3S)-2-amino-3-hydroxybutanoic acidL-allothreonine24830-94-2C[C@H](O)[C@H](N)C(O)=OInChI=1S/C4H9NO3/c1-2(6)3(5)4(7)8/h2-3,6H,5H2,1H3,(H,7,8)/t2-,3-/m0/s1AYFVYJQAPQTCCC-HRFVKAFMSA-NSolidCytosollogp-3.01logs0.60solubility4.77e+02 g/lmelting_point256 oClogp-3.5pka_strongest_acidic2.21pka_strongest_basic9iupac(2S,3S)-2-amino-3-hydroxybutanoic acidaverage_mass119.1192mono_mass119.058243159smilesC[C@H](O)[C@H](N)C(O)=OformulaC4H9NO3inchiInChI=1S/C4H9NO3/c1-2(6)3(5)4(7)8/h2-3,6H,5H2,1H3,(H,7,8)/t2-,3-/m0/s1inchikeyAYFVYJQAPQTCCC-HRFVKAFMSA-Npolar_surface_area83.55refractivity26.46polarizability11.08rotatable_bond_count2acceptor_count4donor_count3physiological_charge0formal_charge0Pyrimidine metabolismThe metabolism of pyrimidines begins with L-glutamine interacting with water molecule and a hydrogen carbonate through an ATP driven carbamoyl phosphate synthetase resulting in a hydrogen ion, an ADP, a phosphate, an L-glutamic acid and a carbamoyl phosphate. The latter compound interacts with an L-aspartic acid through a aspartate transcarbamylase resulting in a phosphate, a hydrogen ion and a N-carbamoyl-L-aspartate. The latter compound interacts with a hydrogen ion through a dihydroorotase resulting in the release of a water molecule and a 4,5-dihydroorotic acid. This compound interacts with an ubiquinone-1 through a dihydroorotate dehydrogenase, type 2 resulting in a release of an ubiquinol-1 and an orotic acid. The orotic acid then interacts with a phosphoribosyl pyrophosphate through a orotate phosphoribosyltransferase resulting in a pyrophosphate and an orotidylic acid. The latter compound then interacts with a hydrogen ion through an orotidine-5 '-phosphate decarboxylase, resulting in an release of carbon dioxide and an Uridine 5' monophosphate. The Uridine 5' monophosphate process to get phosphorylated by an ATP driven UMP kinase resulting in the release of an ADP and an Uridine 5--diphosphate.
Uridine 5-diphosphate can be metabolized in multiple ways in order to produce a Deoxyuridine triphosphate.
1.-Uridine 5-diphosphate interacts with a reduced thioredoxin through a ribonucleoside diphosphate reductase 1 resulting in the release of a water molecule and an oxidized thioredoxin and an dUDP. The dUDP is then phosphorylated by an ATP through a nucleoside diphosphate kinase resulting in the release of an ADP and a DeoxyUridine triphosphate.
2.-Uridine 5-diphosphate interacts with a reduced NrdH glutaredoxin-like protein through a Ribonucleoside-diphosphate reductase 1 resulting in a release of a water molecule, an oxidized NrdH glutaredoxin-like protein and a dUDP. The dUDP is then phosphorylated by an ATP through a nucleoside diphosphate kinase resulting in the release of an ADP and a DeoxyUridine triphosphate.
3.-Uridine 5-diphosphate is phosphorylated by an ATP-driven nucleoside diphosphate kinase resulting in an ADP and an Uridinetriphosphate. The latter compound interacts with a reduced flavodoxin through ribonucleoside-triphosphate reductase resulting in the release of an oxidized flavodoxin, a water molecule and a Deoxyuridine triphosphate
4.-Uridine 5-diphosphate is phosphorylated by an ATP-driven nucleoside diphosphate kinase resulting in an ADP and an Uridinetriphosphate The uridine triphosphate interacts with a L-glutamine and a water molecule through an ATP driven CTP synthase resulting in an ADP, a phosphate, a hydrogen ion, an L-glutamic acid and a cytidine triphosphate. The cytidine triphosphate interacts with a reduced flavodoxin through a ribonucleoside-triphosphate reductase resulting in the release of a water molecule, an oxidized flavodoxin and a dCTP. The dCTP interacts with a water molecule and a hydrogen ion through a dCTP deaminase resulting in a release of an ammonium molecule and a Deoxyuridine triphosphate.
5.-Uridine 5-diphosphate is phosphorylated by an ATP-driven nucleoside diphosphate kinase resulting in an ADP and an Uridinetriphosphate The uridine triphosphate interacts with a L-glutamine and a water molecule through an ATP driven CTP synthase resulting in an ADP, a phosphate, a hydrogen ion, an L-glutamic acid and a cytidine triphosphate. The cytidine triphosphate then interacts spontaneously with a water molecule resulting in the release of a phosphate, a hydrogen ion and a CDP. The CDP then interacts with a reduced NrdH glutaredoxin-like protein through a ribonucleoside-diphosphate reductase 2 resulting in the release of a water molecule, an oxidized NrdH glutaredoxin-like protein and a dCDP. The dCDP is then phosphorylated through an ATP driven nucleoside diphosphate kinase resulting in an ADP and a dCTP. The dCTP interacts with a water molecule and a hydrogen ion through a dCTP deaminase resulting in a release of an ammonium molecule and a Deoxyuridine triphosphate.
6.-Uridine 5-diphosphate is phosphorylated by an ATP-driven nucleoside diphosphate kinase resulting in an ADP and an Uridinetriphosphate The uridine triphosphate interacts with a L-glutamine and a water molecule through an ATP driven CTP synthase resulting in an ADP, a phosphate, a hydrogen ion, an L-glutamic acid and a cytidine triphosphate. The cytidine triphosphate then interacts spontaneously with a water molecule resulting in the release of a phosphate, a hydrogen ion and a CDP. The CDP interacts with a reduced thioredoxin through a ribonucleoside diphosphate reductase 1 resulting in a release of a water molecule, an oxidized thioredoxin and a dCDP. The dCDP is then phosphorylated through an ATP driven nucleoside diphosphate kinase resulting in an ADP and a dCTP. The dCTP interacts with a water molecule and a hydrogen ion through a dCTP deaminase resulting in a release of an ammonium molecule and a Deoxyuridine triphosphate.
The deoxyuridine triphosphate then interacts with a water molecule through a nucleoside triphosphate pyrophosphohydrolase resulting in a release of a hydrogen ion, a phosphate and a dUMP. The dUMP then interacts with a methenyltetrahydrofolate through a thymidylate synthase resulting in a dihydrofolic acid and a 5-thymidylic acid. Then 5-thymidylic acid is then phosphorylated through a nucleoside diphosphate kinase resulting in the release of an ADP and thymidine 5'-triphosphate.PW000942ec00240MetabolicGlycine, serine and threonine metabolismec00260Specdb::CMs873Specdb::CMs3335Specdb::CMs30801Specdb::CMs31722Specdb::CMs31723Specdb::CMs38691Specdb::CMs168754Specdb::NmrOneD1987Specdb::NmrOneD41322Specdb::NmrOneD41323Specdb::NmrOneD41324Specdb::NmrOneD41325Specdb::NmrOneD41326Specdb::NmrOneD41327Specdb::NmrOneD41328Specdb::NmrOneD41329Specdb::NmrOneD41330Specdb::NmrOneD41331Specdb::NmrOneD41332Specdb::NmrOneD41333Specdb::NmrOneD41334Specdb::NmrOneD41335Specdb::NmrOneD41336Specdb::NmrOneD41337Specdb::NmrOneD41338Specdb::NmrOneD41339Specdb::NmrOneD41340Specdb::NmrOneD41341Specdb::MsMs6410Specdb::MsMs6411Specdb::MsMs6412Specdb::MsMs6413Specdb::MsMs6423Specdb::MsMs6424Specdb::MsMs438491Specdb::MsMs438492Specdb::MsMs438493Specdb::MsMs438494Specdb::MsMs439090Specdb::MsMs439187Specdb::MsMs2227172Specdb::MsMs2227548Specdb::MsMs2229885Specdb::MsMs6414Specdb::MsMs6415Specdb::MsMs6416Specdb::MsMs6417Specdb::MsMs6418Specdb::MsMs6420Specdb::MsMs6421Specdb::MsMs6422Specdb::MsMs447025Specdb::MsMs447026Specdb::NmrTwoD1922HMDB040419928989699C0551932826L-ALLO-THREONINEALOKeseler, I. 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Chemical & Pharmaceutical Bulletin (2002), 50(2), 287-291.http://hmdb.ca/system/metabolites/msds/000/003/622/original/HMDB04041.pdf?1358463166Serine hydroxymethyltransferaseP0A825GLYA_ECOLIglyAhttp://ecmdb.ca/proteins/P0A825.xmlLow specificity L-threonine aldolaseP75823LTAE_ECOLIltaEhttp://ecmdb.ca/proteins/P75823.xmlNADP-dependent L-serine/L-allo-threonine dehydrogenase ydfGP39831YDFG_ECOLIydfGhttp://ecmdb.ca/proteins/P39831.xmlL-Allothreonine > Acetaldehyde + GlycineR06171LTAA-RXNL-Allothreonine + NADP <> L-2-Amino-3-oxobutanoic acid + Hydrogen ion + NADPHL-Allothreonine <> Glycine + AcetaldehydeR06171L-Allothreonine + NADP + L-2-Amino-3-oxobutanoic acid <> Aminoacetone + Carbon dioxide + NADPH + Hydrogen ionR10852 L-Allothreonine > Acetaldehyde + GlycineL-Allothreonine > Acetaldehyde + Glycine