2.02012-10-10 12:17:32 -06002015-06-03 17:25:58 -0600ECMDB23122M2MDB0035121-Deoxy-L-glycero-tetrulose 4-phosphate1-deoxy-L-glycero-tetrulose 4-phosphate is an intermediate in the synthesis of riboflavin. It is a substrate for the enzyme 6,7-dimethyl-8-ribityllumazine synthase (RibE) which catalyzes the formation of 6,7-dimethyl-8 ribityllumazine by condensation of 5-amino-6-(D-ribitylamino)uracil with 1-deoxy-L-glycero-tetrulose 4-phosphate. This is the penultimate step in the biosynthesis of riboflavin.(2-hydroxy-3-oxobutyl) dihydrogen phosphate(2-Hydroxy-3-oxobutyl) dihydrogen phosphoric acid1-Deoxy-L-glycero-tetrulose 4-phosphoric acid2-Hydroxy-3-oxobutyl dihydrogen phosphate2-Hydroxy-3-oxobutyl dihydrogen phosphoric acid2-Hydroxy-3-oxobutyl phosphate2-Hydroxy-3-oxobutyl phosphoric acid3,4-Dihydroxy-2-butanone 4-phosphate3,4-Dihydroxy-2-butanone 4-phosphoric acidL-3,4-Dihydroxybutan-2-one 4-phosphateL-3,4-Dihydroxybutan-2-one 4-phosphoric acidC4H9O6P184.0844184.013674532(2-hydroxy-3-oxobutoxy)phosphonic acid2-hydroxy-3-oxobutyl phosphateCC(=O)C(O)COP(O)(O)=OInChI=1S/C4H9O6P/c1-3(5)4(6)2-10-11(7,8)9/h4,6H,2H2,1H3,(H2,7,8,9)OKYHYXLCTGGOLM-UHFFFAOYSA-Nlogp-1.62logs-0.87solubility2.49e+01 g/llogp-1.3pka_strongest_acidic1.39pka_strongest_basic-3.8iupac(2-hydroxy-3-oxobutoxy)phosphonic acidaverage_mass184.0844mono_mass184.013674532smilesCC(=O)C(O)COP(O)(O)=OformulaC4H9O6PinchiInChI=1S/C4H9O6P/c1-3(5)4(6)2-10-11(7,8)9/h4,6H,2H2,1H3,(H2,7,8,9)inchikeyOKYHYXLCTGGOLM-UHFFFAOYSA-Npolar_surface_area104.06refractivity34.81polarizability14.38rotatable_bond_count4acceptor_count5donor_count3physiological_charge-2formal_charge0Flavin biosynthesisThe process of flavin biosynthesis starts with GTP being metabolized by interacting with 3 molecules of water through a GTP cyclohydrolase resulting in a release of formic acid, a pyrophosphate, two hydrog ions and 2,5-diamino-6-(5-phospho-D-ribosylamino)pyrimidin-4(3H)-one or 2,5-Diamino-6-hydroxy-4-(5-phosphoribosylamino)pyrimidine. Either of these compounds interacts with a water molecule and a hydrogen ion through a fused diaminohydroxyphosphoribosylaminopyrimidine deaminase / 5-amino-6-(5-phosphoribosylamino)uracil reductase resulting in an ammonium and 5-amino-6-(5-phospho-D-ribosylamino)uracil. This compound then interacts with a hydrogen ion through a NADPH dependent fused diaminohydroxyphosphoribosylaminopyrimidine deaminase / 5-amino-6-(5-phosphoribosylamino)uracil reductase resulting in the release of a NADP and a 5-amino-6-(5-phospho-D-ribitylamino)uracil. This compound then interacts with a water molecule through a 5-amino-6-(5-phospho-D-ribitylamino)uracil phosphatase resulting in a release of a phosphate, and a 5-amino-6-(D-ribitylamino)uracil.
D-ribulose 5-phosphate interacts with a3,4-dihydroxy-2-butanone 4-phosphate synthase resulting in the release of formic acid, a hydrogen ion and 1-deoxy-L-glycero-tetrulose 4-phosphate.
A 5-amino-6-(D-ribitylamino)uracil and 1-deoxy-L-glycero-tetrulose 4-phosphate interact through a 6,7-dimethyl-8-ribityllumazine synthase resulting in the release of 2 water molecules, a phosphate, a hydrogen ion and a 6,7-dimethyl-8-(1-D-ribityl)lumazine.
The latter compound then interacts with a hydrogen ion through a riboflavin synthase resulting in the release of a riboflavin and a 5-amino-6-(d-ribitylamino)uracil.
The riboflavin is then phosphorylated through an ATP dependent riboflavin kinase resulting in the release of a ADP, a hydrogen ion and a FLAVIN MONONUCLEOTIDE.
The flavin mononucleotide interad with a hydrogen ion and an ATP through the riboflavin kinase resulting in the release of a pyrophosphate and Flavin Adenine dinucleotide. This compound is then exported into the periplasm through a FMN/FAD exporter.
PW001971MetabolicSpecdb::CMs3053Specdb::NmrOneD290555Specdb::NmrOneD290556Specdb::NmrOneD290557Specdb::NmrOneD290558Specdb::NmrOneD290559Specdb::NmrOneD290560Specdb::NmrOneD290561Specdb::NmrOneD290562Specdb::NmrOneD290563Specdb::NmrOneD290564Specdb::NmrOneD290565Specdb::NmrOneD290566Specdb::NmrOneD290567Specdb::NmrOneD290568Specdb::NmrOneD290569Specdb::NmrOneD290570Specdb::NmrOneD290571Specdb::NmrOneD290572Specdb::NmrOneD290573Specdb::NmrOneD290574Specdb::MsMs25145Specdb::MsMs25146Specdb::MsMs25147Specdb::MsMs31703Specdb::MsMs31704Specdb::MsMs31705Specdb::MsMs3607813Specdb::MsMs3607814Specdb::MsMs3607815Specdb::MsMs3607816Specdb::MsMs3607817Specdb::MsMs3607818669C15556506083,4-dihydroxy-2-butanone 4-phosphate synthaseP0A7J0RIBB_ECOLIribBhttp://ecmdb.ca/proteins/P0A7J0.xmlRiboflavin synthase alpha chainP0AFU8RISA_ECOLIribEhttp://ecmdb.ca/proteins/P0AFU8.xml2-C-methyl-D-erythritol 4-phosphate cytidylyltransferaseQ46893ISPD_ECOLIispDhttp://ecmdb.ca/proteins/Q46893.xmlD-Ribulose 5-phosphate > Formic acid + 1-Deoxy-L-glycero-tetrulose 4-phosphateD-Ribulose 5-phosphate > 1-Deoxy-L-glycero-tetrulose 4-phosphate + Formic acid + Hydrogen ionPW_R0038465-Amino-6-ribitylamino uracil + 1-Deoxy-L-glycero-tetrulose 4-phosphate > Water + Phosphate + Hydrogen ion + 6,7-Dimethyl-8-(1-D-ribityl)lumazine + 6,7-Dimethyl-8-(1-D-ribityl)lumazinePW_R005556