2.02012-05-31 14:02:31 -06002015-10-15 16:14:21 -0600ECMDB04024M2MDB000564BetaineBetaine or trimethylglycine is a methylated derivative of glycine. It functions as a methyl donor in that it carries and donates methyl functional groups to facilitate necessary chemical processes. Betaine is an osmoprotectant compound. The accumulation of betaine increases the volume of cytoplasmic water of E. coli and increases the growth rate of osmotically stressed E. coli. (PMID: 1537801)(Carboxymethyl)trimethylammonium hydroxide inner salt(Trimethylammonio)acetate(Trimethylammonio)acetic acid1-Carboxy-N,N,N-trimethyl-Methanaminium1-Carboxy-N,N,N-trimethyl-Methanaminium hydroxide1-Carboxy-N,N,N-trimethylmethanaminium inner salt<i>N,N,N</i>-trimethylglycineA-EarleineAbromineAcidin-pepsinAlpha-EarleineAminocoatBetafinBetafin BCRBetafin BPBetaineCystadaneEktasolve EEFinnStimGlycine betaineGlycocoll betaineGlycylbetaineGreenstimLoramine AMB 13Loramine AMB-13LycineN,N,N-TrimethylglycineOxyneurineRubrine CTrimethylaminoacetateTrimethylaminoacetic acidTrimethylammonioacetateTrimethylammonioacetic acidTrimethylbetaine GlycineTrimethylglycineTrimethylglycocollα-EarleineC5H12NO2118.1543118.086803633(carboxymethyl)trimethylazaniumtrimethyl glycine107-43-7C[N+](C)(C)CC(O)=OInChI=1S/C5H11NO2/c1-6(2,3)4-5(7)8/h4H2,1-3H3/p+1KWIUHFFTVRNATP-UHFFFAOYSA-OSolidCytosolExtra-organismPeriplasmlogp-2.12logs-1.94solubility1.75e+00 g/lmelting_point293 oC ( Soicke, H., Fitoterapia 1988, V59(1), P73-5); 301 oC dec.logp-4.5pka_strongest_acidic2.26iupac(carboxymethyl)trimethylazaniumaverage_mass118.1543mono_mass118.086803633smilesC[N+](C)(C)CC(O)=OformulaC5H12NO2inchiInChI=1S/C5H11NO2/c1-6(2,3)4-5(7)8/h4H2,1-3H3/p+1inchikeyKWIUHFFTVRNATP-UHFFFAOYSA-Opolar_surface_area37.3refractivity41.99polarizability12.52rotatable_bond_count2acceptor_count2donor_count1physiological_charge0formal_charge1Glycine, serine and threonine metabolismec00260ABC transportersec02010Metabolic pathwayseco01100Quorum SensingBacterial 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 phosphatePW000836SignalingS-adenosyl-L-methionine cycleThe S-adenosyl-L-methionine cycle starts with S-adenosyl-L-methionine reacting with (a demethylated methyl donor ) dimethylglycine resulting in the release of a hydrogen ion, a betain (a methylated methyl donor) and a S-adenosyl-L-homocysteine. The s-adenosyl-L-homocysteine reacts with a water molecule through a S-adenosylhomocysteine nucleosidase resulting in the release of a adenine and a ribosyl-L-homocysteine. This compound in turn reacts with a s-ribosylhomocysteine lyase resulting in the release of a l-homocysteine and a autoinducer 2. The L-homocysteine reacts with a N5-methyl-tetrahydropteroyl tri-L-glutamate through a methionine synthase resulting in the release of a tetrahydropteroyl tri-L-glutamate and a methione. The methionine in turn reacts with a water molecule and ATP molecule through a methionine adenosyltransferase resulting in the release of a diphosphate, a phosphate and a s-adenosyl-L-methionine.PW002080Metabolicglycine betaine biosynthesis I (Gram-negative bacteria)BETSYN-PWYSpecdb::CMs6600Specdb::CMs47811Specdb::CMs146551Specdb::CMs1047404Specdb::EiMs2013Specdb::NmrOneD5276Specdb::NmrOneD5277Specdb::NmrOneD166377Specdb::NmrOneD166433Specdb::NmrOneD166538Specdb::NmrOneD166643Specdb::MsMs912835Specdb::MsMs912836Specdb::MsMs912837Specdb::MsMs1470719Specdb::MsMs1470720Specdb::MsMs1470721Specdb::MsMs1470722Specdb::MsMs1470723Specdb::MsMs1470724Specdb::MsMs1470725Specdb::MsMs1470726Specdb::MsMs1470727Specdb::MsMs1470728Specdb::MsMs1470729Specdb::MsMs1470730Specdb::MsMs1470731Specdb::MsMs1470732Specdb::MsMs1470733Specdb::MsMs1470734Specdb::MsMs1470735Specdb::MsMs1470736Specdb::MsMs1470737Specdb::MsMs1470738Specdb::MsMs1470739Specdb::MsMs1470740Specdb::NmrTwoD2084Specdb::NmrTwoD2085HMDB00043247242C0071917750BETAINEBETBetaineKeseler, 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 80:2939-2948.18331064Cayley, S., Lewis, B. A., Record, M. T. Jr (1992). "Origins of the osmoprotective properties of betaine and proline in Escherichia coli K-12." J Bacteriol 174:1586-1595.1537801Mu, Yun; Guo, Xiao-hui. Improved process for preparation of betaine. Huaxue Yu Shengwu Gongcheng (2005), 22(7), 48-49. http://hmdb.ca/system/metabolites/msds/000/000/030/original/HMDB00043.pdf?1358461909Betaine aldehyde dehydrogenaseP17445BETB_ECOLIbetBhttp://ecmdb.ca/proteins/P17445.xmlGlycine betaine/L-proline transport system permease protein proWP14176PROW_ECOLIproWhttp://ecmdb.ca/proteins/P14176.xmlPutative osmoprotectant uptake system permease protein yehWP33359YEHW_ECOLIyehWhttp://ecmdb.ca/proteins/P33359.xmlPutative osmoprotectant uptake system permease protein yehYP33361YEHY_ECOLIyehYhttp://ecmdb.ca/proteins/P33361.xmlPutative osmoprotectant uptake system ATP-binding protein yehXP33360YEHX_ECOLIyehXhttp://ecmdb.ca/proteins/P33360.xmlPutative osmoprotectant uptake system substrate-binding protein osmFP33362OSMF_ECOLIosmFhttp://ecmdb.ca/proteins/P33362.xmlUncharacterized transporter YeaVP0ABD1YEAV_ECOLIyeaVhttp://ecmdb.ca/proteins/P0ABD1.xmlProline/betaine transporterP0C0L7PROP_ECOLIproPhttp://ecmdb.ca/proteins/P0C0L7.xmlGlycine betaine/L-proline transport system permease protein proWP14176PROW_ECOLIproWhttp://ecmdb.ca/proteins/P14176.xmlPutative osmoprotectant uptake system permease protein yehWP33359YEHW_ECOLIyehWhttp://ecmdb.ca/proteins/P33359.xmlPutative osmoprotectant uptake system permease protein yehYP33361YEHY_ECOLIyehYhttp://ecmdb.ca/proteins/P33361.xmlOuter membrane protein NP77747OMPN_ECOLIompNhttp://ecmdb.ca/proteins/P77747.xmlPutative osmoprotectant uptake system ATP-binding protein yehXP33360YEHX_ECOLIyehXhttp://ecmdb.ca/proteins/P33360.xmlOuter membrane pore protein EP02932PHOE_ECOLIphoEhttp://ecmdb.ca/proteins/P02932.xmlOuter membrane protein FP02931OMPF_ECOLIompFhttp://ecmdb.ca/proteins/P02931.xmlPutative osmoprotectant uptake system substrate-binding protein osmFP33362OSMF_ECOLIosmFhttp://ecmdb.ca/proteins/P33362.xmlOuter membrane protein CP06996OMPC_ECOLIompChttp://ecmdb.ca/proteins/P06996.xmlAdenosine triphosphate + Water + Betaine > ADP + Betaine + Hydrogen ion + PhosphateAdenosine triphosphate + Water + Betaine > ADP + Betaine + Hydrogen ion + PhosphateBetaine aldehyde + Water + NADP > Betaine +2 Hydrogen ion + NADPHR02566Betaine aldehyde + Water + NAD <> Betaine +2 Hydrogen ion + NADHR02565BADH-RXNBetaine aldehyde + NADP + Water <> Betaine + NADPH +2 Hydrogen ionR02566Betaine aldehyde + NAD + Water > Hydrogen ion + Betaine + NADHR02565BADH-RXNBetaine aldehyde + NAD + Water > Betaine + NADHBetaine aldehyde + Water + NADP > Betaine +2 Hydrogen ion + NADPHBetaine aldehyde + Water + NADP > Betaine +2 Hydrogen ion + NADPH