2.0 2012-05-31 14:02:31 -0600 2015-10-15 16:14:21 -0600 ECMDB04024 M2MDB000564 Betaine Betaine 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 acid 1-Carboxy-N,N,N-trimethyl-Methanaminium 1-Carboxy-N,N,N-trimethyl-Methanaminium hydroxide 1-Carboxy-N,N,N-trimethylmethanaminium inner salt <i>N,N,N</i>-trimethylglycine A-Earleine Abromine Acidin-pepsin Alpha-Earleine Aminocoat Betafin Betafin BCR Betafin BP Betaine Cystadane Ektasolve EE FinnStim Glycine betaine Glycocoll betaine Glycylbetaine Greenstim Loramine AMB 13 Loramine AMB-13 Lycine N,N,N-Trimethylglycine Oxyneurine Rubrine C Trimethylaminoacetate Trimethylaminoacetic acid Trimethylammonioacetate Trimethylammonioacetic acid Trimethylbetaine Glycine Trimethylglycine Trimethylglycocoll α-Earleine C5H12NO2 118.1543 118.086803633 (carboxymethyl)trimethylazanium trimethyl glycine 107-43-7 C[N+](C)(C)CC(O)=O InChI=1S/C5H11NO2/c1-6(2,3)4-5(7)8/h4H2,1-3H3/p+1 KWIUHFFTVRNATP-UHFFFAOYSA-O Solid Cytosol Extra-organism Periplasm logp -2.12 ALOGPS logs -1.94 ALOGPS solubility 1.75e+00 g/l ALOGPS melting_point 293 oC ( Soicke, H., Fitoterapia 1988, V59(1), P73-5); 301 oC dec. logp -4.5 ChemAxon pka_strongest_acidic 2.26 ChemAxon iupac (carboxymethyl)trimethylazanium ChemAxon average_mass 118.1543 ChemAxon mono_mass 118.086803633 ChemAxon smiles C[N+](C)(C)CC(O)=O ChemAxon formula C5H12NO2 ChemAxon inchi InChI=1S/C5H11NO2/c1-6(2,3)4-5(7)8/h4H2,1-3H3/p+1 ChemAxon inchikey KWIUHFFTVRNATP-UHFFFAOYSA-O ChemAxon polar_surface_area 37.3 ChemAxon refractivity 41.99 ChemAxon polarizability 12.52 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 1 ChemAxon Glycine, serine and threonine metabolism ec00260 ABC transporters ec02010 Metabolic pathways eco01100 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 S-adenosyl-L-methionine cycle The 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. PW002080 Metabolic glycine betaine biosynthesis I (Gram-negative bacteria) BETSYN-PWY Specdb::CMs 6600 Specdb::CMs 47811 Specdb::CMs 146551 Specdb::CMs 1047404 Specdb::EiMs 2013 Specdb::NmrOneD 5276 Specdb::NmrOneD 5277 Specdb::NmrOneD 166377 Specdb::NmrOneD 166433 Specdb::NmrOneD 166538 Specdb::NmrOneD 166643 Specdb::MsMs 912835 Specdb::MsMs 912836 Specdb::MsMs 912837 Specdb::MsMs 1470719 Specdb::MsMs 1470720 Specdb::MsMs 1470721 Specdb::MsMs 1470722 Specdb::MsMs 1470723 Specdb::MsMs 1470724 Specdb::MsMs 1470725 Specdb::MsMs 1470726 Specdb::MsMs 1470727 Specdb::MsMs 1470728 Specdb::MsMs 1470729 Specdb::MsMs 1470730 Specdb::MsMs 1470731 Specdb::MsMs 1470732 Specdb::MsMs 1470733 Specdb::MsMs 1470734 Specdb::MsMs 1470735 Specdb::MsMs 1470736 Specdb::MsMs 1470737 Specdb::MsMs 1470738 Specdb::MsMs 1470739 Specdb::MsMs 1470740 Specdb::NmrTwoD 2084 Specdb::NmrTwoD 2085 HMDB00043 247 242 C00719 17750 BETAINE BET Betaine 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 Kanehisa, 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. 22080510 van 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. 17765195 Winder, 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. 18331064 Cayley, 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. 1537801 Mu, 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?1358461909 Betaine aldehyde dehydrogenase P17445 BETB_ECOLI betB http://ecmdb.ca/proteins/P17445.xml Glycine betaine/L-proline transport system permease protein proW P14176 PROW_ECOLI proW http://ecmdb.ca/proteins/P14176.xml Putative osmoprotectant uptake system permease protein yehW P33359 YEHW_ECOLI yehW http://ecmdb.ca/proteins/P33359.xml Putative osmoprotectant uptake system permease protein yehY P33361 YEHY_ECOLI yehY http://ecmdb.ca/proteins/P33361.xml Putative osmoprotectant uptake system ATP-binding protein yehX P33360 YEHX_ECOLI yehX http://ecmdb.ca/proteins/P33360.xml Putative osmoprotectant uptake system substrate-binding protein osmF P33362 OSMF_ECOLI osmF http://ecmdb.ca/proteins/P33362.xml Uncharacterized transporter YeaV P0ABD1 YEAV_ECOLI yeaV http://ecmdb.ca/proteins/P0ABD1.xml Proline/betaine transporter P0C0L7 PROP_ECOLI proP http://ecmdb.ca/proteins/P0C0L7.xml Glycine betaine/L-proline transport system permease protein proW P14176 PROW_ECOLI proW http://ecmdb.ca/proteins/P14176.xml Putative osmoprotectant uptake system permease protein yehW P33359 YEHW_ECOLI yehW http://ecmdb.ca/proteins/P33359.xml Putative osmoprotectant uptake system permease protein yehY P33361 YEHY_ECOLI yehY http://ecmdb.ca/proteins/P33361.xml Outer membrane protein N P77747 OMPN_ECOLI ompN http://ecmdb.ca/proteins/P77747.xml Putative osmoprotectant uptake system ATP-binding protein yehX P33360 YEHX_ECOLI yehX http://ecmdb.ca/proteins/P33360.xml Outer membrane pore protein E P02932 PHOE_ECOLI phoE http://ecmdb.ca/proteins/P02932.xml Outer membrane protein F P02931 OMPF_ECOLI ompF http://ecmdb.ca/proteins/P02931.xml Putative osmoprotectant uptake system substrate-binding protein osmF P33362 OSMF_ECOLI osmF http://ecmdb.ca/proteins/P33362.xml Outer membrane protein C P06996 OMPC_ECOLI ompC http://ecmdb.ca/proteins/P06996.xml Adenosine triphosphate + Water + Betaine > ADP + Betaine + Hydrogen ion + Phosphate Adenosine triphosphate + Water + Betaine > ADP + Betaine + Hydrogen ion + Phosphate Betaine aldehyde + Water + NADP > Betaine +2 Hydrogen ion + NADPH R02566 Betaine aldehyde + Water + NAD <> Betaine +2 Hydrogen ion + NADH R02565 BADH-RXN Betaine aldehyde + NADP + Water <> Betaine + NADPH +2 Hydrogen ion R02566 Betaine aldehyde + NAD + Water > Hydrogen ion + Betaine + NADH R02565 BADH-RXN Betaine aldehyde + NAD + Water > Betaine + NADH Betaine aldehyde + Water + NADP > Betaine +2 Hydrogen ion + NADPH Betaine aldehyde + Water + NADP > Betaine +2 Hydrogen ion + NADPH