2.0 2012-07-30 14:55:30 -0600 2015-09-17 15:42:05 -0600 ECMDB21368 M2MDB001764 (2R,4S)-2-Methyl-2,3,3,4-tetrahydroxytetrahydrofuran (2R,4S)-2-methyl-2,3,3,4-tetrahydroxytetrahydrofuran, also known as autoinducer 2 (AI-2), is a member of the chemical class known as Oxolanes. These are organic compounds containing an oxolane (tetrahydrofuran) ring, which is a saturated aliphatic five-member ring containing one oxygen and five carbon atoms. AI-2 is the R isomer of 2-methyl-2,3,3,4-tetrahydroxytetrahydrofuran, so it can be abbreviated as (R)-THMF. Autoinducer 2 (AI-2), a quorum sensing signaling molecule proposed to be involved in interspecies communication, is produced by many species of gram-negative and gram-positive bacteria including E. coli. (PMID 19636340, 15601708, 18256823) AI-2 is spontaneously derived from 4,5-dihydroxy-2,3-pentanedione that, along with homocysteine, is produced by cleavage of S-adenosylhomocysteine (SAH) and S-ribosylhomocysteine by the Pfs and LuxS enzymes. (PMID 16885435) Both LsrB and Tsr are necessary for sensing AI-2. LsrB binds AI-2 in the periplasm, and Tsr is the L-serine chemoreceptor. (PMID 21097621) (<i>R</i>)-THMF (R)-THMF AI-2 AI-2 (salmonella) Auto inducer 2 C5H10O5 150.13 150.052823422 (2S,4R)-2-methyloxolane-2,3,3,4-tetrol (2S,4R)-2-methyloxolane-2,3,3,4-tetrol CC1(O)OCC(O)C1(O)O InChI=1S/C5H10O5/c1-4(7)5(8,9)3(6)2-10-4/h3,6-9H,2H2,1H3 BVIYGXUQVXBHQS-UHFFFAOYSA-N Cytosol logp -1.96 ALOGPS logs 0.71 ALOGPS solubility 7.66e+02 g/l ALOGPS logp -1.6 ChemAxon pka_strongest_acidic 9.16 ChemAxon pka_strongest_basic -4 ChemAxon iupac (2S,4R)-2-methyloxolane-2,3,3,4-tetrol ChemAxon average_mass 150.13 ChemAxon mono_mass 150.052823422 ChemAxon smiles CC1(O)OCC(O)C1(O)O ChemAxon formula C5H10O5 ChemAxon inchi InChI=1S/C5H10O5/c1-4(7)5(8,9)3(6)2-10-4/h3,6-9H,2H2,1H3 ChemAxon inchikey BVIYGXUQVXBHQS-UHFFFAOYSA-N ChemAxon polar_surface_area 90.15 ChemAxon refractivity 30.49 ChemAxon polarizability 13.34 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 5 ChemAxon donor_count 4 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 inner membrane transport list of inner membrane transport complexes, transporting compounds from the periplasmic space to the cytosol This pathway should be updated regularly with the new inner membrae transports added PW000786 Metabolic autoinducer AI-2 biosynthesis I PWY-6153 Specdb::MsMs 24041 Specdb::MsMs 24042 Specdb::MsMs 24043 Specdb::MsMs 30839 Specdb::MsMs 30840 Specdb::MsMs 30841 448719 26330266 CPD-10774 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 Walters, M., Sircili, M. P., Sperandio, V. (2006). "AI-3 synthesis is not dependent on luxS in Escherichia coli." J Bacteriol 188:5668-5681. 16885435 Xue, T., Zhao, L., Sun, H., Zhou, X., Sun, B. (2009). "LsrR-binding site recognition and regulatory characteristics in Escherichia coli AI-2 quorum sensing." Cell Res 19:1258-1268. 19636340 Hegde, M., Englert, D. L., Schrock, S., Cohn, W. B., Vogt, C., Wood, T. K., Manson, M. D., Jayaraman, A. (2011). "Chemotaxis to the quorum-sensing signal AI-2 requires the Tsr chemoreceptor and the periplasmic LsrB AI-2-binding protein." J Bacteriol 193:768-773. 21097621 Autoinducer 2 import system permease protein lsrC B1XEA2 LSRC_ECODH lsrC http://ecmdb.ca/proteins/B1XEA2.xml Autoinducer 2 import system permease protein lsrD B1XEA3 LSRD_ECODH lsrD http://ecmdb.ca/proteins/B1XEA3.xml Autoinducer 2 import system permease protein lsrD P0AFS1 LSRD_ECOLI lsrD http://ecmdb.ca/proteins/P0AFS1.xml Autoinducer 2 import system permease protein lsrC P77672 LSRC_ECOLI lsrC http://ecmdb.ca/proteins/P77672.xml Autoinducer 2 import ATP-binding protein LsrA P77257 LSRA_ECOLI lsrA http://ecmdb.ca/proteins/P77257.xml Autoinducer 2-binding protein LsrB P76142 LSRB_ECOLI lsrB http://ecmdb.ca/proteins/P76142.xml Water + (2R,4S)-2-Methyl-2,4-dihydroxydihydrofuran-3-one > (2R,4S)-2-Methyl-2,3,3,4-tetrahydroxytetrahydrofuran RXN-10017 (2R,4S)-2-methyl-2,4-dihydroxydihydrofuran-3-one + Water > (2R,4S)-2-Methyl-2,3,3,4-tetrahydroxytetrahydrofuran RXN-10017 (2R,4S)-2-Methyl-2,3,3,4-tetrahydroxytetrahydrofuran + Adenosine triphosphate + Water > (2R,4S)-2-Methyl-2,3,3,4-tetrahydroxytetrahydrofuran + ADP + Phosphate + Hydrogen ion TRANS-RXN0-454 (2R,4S)-2-Methyl-2,3,3,4-tetrahydroxytetrahydrofuran + Adenosine triphosphate + Water > (2R,4S)-2-Methyl-2,3,3,4-tetrahydroxytetrahydrofuran + ADP + Phosphate + Hydrogen ion TRANS-RXN0-454 (2R,4S)-2-methyl-2,3,3,4-tetrahydroxytetrahydrofuran + Adenosine triphosphate + (2R,4S)-2-Methyl-2,3,3,4-tetrahydroxytetrahydrofuran > Adenosine diphosphate + Hydrogen ion + (4S)-4-hydroxy-2,3-pentanedione 5-phosphate + ADP + (4S)-4-hydroxy-2,3-pentanedione 5-phosphate PW_R003071 (2R,4S)-2-methyl-2,3,3,4-tetrahydroxytetrahydrofuran + Phosphoribosyl-ATP + Water + (2R,4S)-2-Methyl-2,3,3,4-tetrahydroxytetrahydrofuran + Phosphoribosyl-ATP > (2R,4S)-2-methyl-2,3,3,4-tetrahydroxytetrahydrofuran + Adenosine diphosphate + Hydrogen ion + Pyrophosphate + ADP PW_RCT000124