2.02012-05-31 14:03:54 -06002015-06-03 15:54:41 -0600ECMDB04060M2MDB0005903,4-Dihydroxy-2-butanone-4-P3,4-dihydroxy-2-butanone-4-p is a member of the chemical class known as Organophosphate Esters. These are organic compounds containing phosphoric acid ester functional group. 3,4-dihydroxy-2-butanone-4-p is invovled in Fravin biosynthesis. r 15;80(8):2939-48.)3,4-dihydroxy-2-butanone-4-P3,4-Dihydroxy-2-butanone-4-phosphate3,4-Dihydroxy-2-butanone-4-phosphoric acid3,4D2B4PDihydroxy-butanone-pL-3,4-Dihydroxybutan-2-one-4-phosphateL-3,4-Dihydroxybutan-2-one-4-phosphoric acidTetrolose phosphateTetrolose phosphoric acidC4H7O6P182.0685181.9980244683-hydroxy-4-(phosphonatooxy)butan-2-one2-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)/p-2OKYHYXLCTGGOLM-UHFFFAOYSA-LCytosollogp-1.20logs-0.56solubility6.05e+01 g/llogp-1.3pka_strongest_acidic1.39pka_strongest_basic-3.8iupac3-hydroxy-4-(phosphonatooxy)butan-2-oneaverage_mass182.0685mono_mass181.998024468smilesCC(=O)C(O)COP([O-])([O-])=OformulaC4H7O6PinchiInChI=1S/C4H9O6P/c1-3(5)4(6)2-10-11(7,8)9/h4,6H,2H2,1H3,(H2,7,8,9)/p-2inchikeyOKYHYXLCTGGOLM-UHFFFAOYSA-Lpolar_surface_area109.72refractivity32.56polarizability14.04rotatable_bond_count4acceptor_count5donor_count1physiological_charge-2formal_charge-2Riboflavin metabolismec00740Metabolic pathwayseco01100Flavin 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.
PW001971Metabolicflavin biosynthesis I (bacteria and plants)RIBOSYN2-PWYSpecdb::NmrOneD283309Specdb::NmrOneD283310Specdb::NmrOneD283311Specdb::NmrOneD283312Specdb::NmrOneD283313Specdb::NmrOneD283314Specdb::NmrOneD283315Specdb::NmrOneD283316Specdb::NmrOneD283317Specdb::NmrOneD283318Specdb::NmrOneD283319Specdb::NmrOneD283320Specdb::NmrOneD283321Specdb::NmrOneD283322Specdb::NmrOneD283323Specdb::NmrOneD283324Specdb::NmrOneD283325Specdb::NmrOneD283326Specdb::NmrOneD283327Specdb::NmrOneD283328Specdb::MsMs24944Specdb::MsMs24945Specdb::MsMs24946Specdb::MsMs31502Specdb::MsMs31503Specdb::MsMs315042198329110739351C1555650606DIHYDROXY-BUTANONE-PKeseler, 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-D590.21097882Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114.22080510van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25.17765195Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948.183310643,4-dihydroxy-2-butanone 4-phosphate synthaseP0A7J0RIBB_ECOLIribBhttp://ecmdb.ca/proteins/P0A7J0.xmlRiboflavin synthase alpha chainP0AFU8RISA_ECOLIribEhttp://ecmdb.ca/proteins/P0AFU8.xml6,7-dimethyl-8-ribityllumazine synthaseP61714RISB_ECOLIribHhttp://ecmdb.ca/proteins/P61714.xml5-Amino-6-ribitylamino uracil + 3,4-Dihydroxy-2-butanone-4-P > 6,7-Dimethyl-8-(1-D-ribityl)lumazine +2 Water + PhosphateR04457D-Ribulose 5-phosphate <> 3,4-Dihydroxy-2-butanone-4-P + Formic acid + Hydrogen ionR07281DIOHBUTANONEPSYN-RXN5-Amino-6-ribitylamino uracil + 3,4-Dihydroxy-2-butanone-4-P <> 6,7-Dimethyl-8-(1-D-ribityl)lumazine +2 Water + PhosphateR04457D-Ribulose 5-phosphate <> 3,4-Dihydroxy-2-butanone-4-P + Formic acidR07281D-Ribulose 5-phosphate > Hydrogen ion + 3,4-Dihydroxy-2-butanone-4-P + Formic acidDIOHBUTANONEPSYN-RXN5-amino-6-(D-ribitylamino)uracil + 3,4-Dihydroxy-2-butanone-4-P > Hydrogen ion + 6,7-Dimethyl-8-(1-D-ribityl)lumazine + Phosphate + WaterLUMAZINESYN-RXND-Ribulose 5-phosphate <>3 3,4-Dihydroxy-2-butanone-4-P + Formic acid + Hydrogen ionD-Ribulose 5-phosphate <>3 3,4-Dihydroxy-2-butanone-4-P + Formic acidD-Ribulose 5-phosphate <>3 3,4-Dihydroxy-2-butanone-4-P + Formic acid + Hydrogen ion