2.0 2012-05-31 14:50:12 -0600 2015-06-03 17:20:12 -0600 ECMDB20550 M2MDB001356 4,5-Dihydroxy-2,3-pentanedione 4,5-dihydroxy-2,3-pentanedione is a member of the chemical class known as Beta Ketoaldehydes. These are organic compounds containing an aldehyde substituted with a keto group on the second carbon atom. Dihydropyrimidine dehydrogenase (DPD) is the initial and rate-limiting enzyme in the catabolism of 5-FU. (PMID 9865912) E. coli expression system is a valuable tool for examining DPD enzymatic variants. (PMID 9439663) (<i>S</i>)-4,5-dihydroxypentan-2,3-dione (S)-4,5-dihydroxypentan-2,3-dione DHPD Dihydroxypentanedione DPD C5H8O4 132.1146 132.042258744 (4R)-4,5-dihydroxypentane-2,3-dione (4R)-4,5-dihydroxypentane-2,3-dione [H][C@@](O)(CO)C(=O)C(C)=O InChI=1S/C5H8O4/c1-3(7)5(9)4(8)2-6/h4,6,8H,2H2,1H3/t4-/m1/s1 UYTRITJAZOPLCZ-SCSAIBSYSA-N Cytosol logp -0.95 ALOGPS logs 0.31 ALOGPS solubility 2.72e+02 g/l ALOGPS logp -0.9 ChemAxon pka_strongest_acidic 11.69 ChemAxon pka_strongest_basic -3 ChemAxon iupac (4R)-4,5-dihydroxypentane-2,3-dione ChemAxon average_mass 132.1146 ChemAxon mono_mass 132.042258744 ChemAxon smiles [H][C@@](O)(CO)C(=O)C(C)=O ChemAxon formula C5H8O4 ChemAxon inchi InChI=1S/C5H8O4/c1-3(7)5(9)4(8)2-6/h4,6,8H,2H2,1H3/t4-/m1/s1 ChemAxon inchikey UYTRITJAZOPLCZ-SCSAIBSYSA-N ChemAxon polar_surface_area 74.6 ChemAxon refractivity 29.28 ChemAxon polarizability 11.94 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Quorum Sensing Bacterial Autoinducer 2 (AI-2) mediates the quorum sensing 2 system. AI-2 is catalyzed by the luxS enzyme. This enzyme is found in E.coli and S.typhimurium. In E. coli and most pathogenic bacteria that form AI-2 are spontaneous transformations that include cyclization to (2R,4S)-2-methyl-2,4-dihydroxydihydrofuran-3-one and hydration to the final autoinducer (2R,4S)-2-methyl-2,3,3,4-tetrahydroxytetrahydrofuran. This product is released from the cell through the AI-2 transporter (tqsA). As the level of AI-2 increases, other cells detect it and import it through the autoinducer-2 ABC transporter (lsrACDB). AI-2 is then degraded in the cells by phosphorylating the AI-2 which is then isomerized to P-HPD which follows by the transfer of and acetyl group to coenzyme A and releases dihydroxyacetone phosphate PW000836 Signaling <i>S</i>-adenosyl-L-methionine cycle I PWY-6151 autoinducer AI-2 biosynthesis I PWY-6153 Specdb::CMs 1086336 Specdb::NmrOneD 256648 Specdb::NmrOneD 256649 Specdb::NmrOneD 256650 Specdb::NmrOneD 256651 Specdb::NmrOneD 256652 Specdb::NmrOneD 256653 Specdb::NmrOneD 256654 Specdb::NmrOneD 256655 Specdb::NmrOneD 256656 Specdb::NmrOneD 256657 Specdb::NmrOneD 256658 Specdb::NmrOneD 256659 Specdb::NmrOneD 256660 Specdb::NmrOneD 256661 Specdb::NmrOneD 256662 Specdb::NmrOneD 256663 Specdb::NmrOneD 256664 Specdb::NmrOneD 256665 Specdb::NmrOneD 256666 Specdb::NmrOneD 256667 Specdb::MsMs 28424 Specdb::MsMs 28425 Specdb::MsMs 28426 Specdb::MsMs 34982 Specdb::MsMs 34983 Specdb::MsMs 34984 25200942 23260085 DIHYDROXYPENTANEDIONE Keseler, 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. 21097882 Vreken, P., Van Kuilenburg, A. B., Meinsma, R., van Gennip, A. H. (1997). "Dihydropyrimidine dehydrogenase (DPD) deficiency: identification and expression of missense mutations C29R, R886H and R235W." Hum Genet 101:333-338. 9439663 Kouwaki, M., Hamajima, N., Sumi, S., Nonaka, M., Sasaki, M., Dobashi, K., Kidouchi, K., Togari, H., Wada, Y. (1998). "Identification of novel mutations in the dihydropyrimidine dehydrogenase gene in a Japanese patient with 5-fluorouracil toxicity." Clin Cancer Res 4:2999-3004. 9865912 S-ribosylhomocysteine lyase P45578 LUXS_ECOLI luxS http://ecmdb.ca/proteins/P45578.xml S-Ribosyl-L-homocysteine > 4,5-Dihydroxy-2,3-pentanedione + L-Homocysteine RIBOSYLHOMOCYSTEINASE-RXN 4,5-Dihydroxy-2,3-pentanedione > (2R,4S)-2-Methyl-2,4-dihydroxydihydrofuran-3-one RXN-10015 4,5-Dihydroxy-2,3-pentanedione > (2R,4S)-2-methyl-2,4-dihydroxydihydrofuran-3-one RXN-10015 4,5-Dihydroxy-2,3-pentanedione > (2S,4S)-2-methyl-2,4-dihydroxydihydrofuran-3-one RXN-10016 4,5-Dihydroxy-2,3-pentanedione + Adenosine triphosphate > Hydrogen ion + P-DPD + ADP RXN0-5461 S-ribosyl-L-homocysteine > 4,5-Dihydroxy-2,3-pentanedione + Homocysteine PW_R005929