2.0 2012-05-31 10:25:15 -0600 2015-09-13 15:15:18 -0600 ECMDB00271 M2MDB000112 Sarcosine Sarcosine, also known as N-methylglycine, is an intermediate and byproduct in glycine synthesis and degradation. Sarcosine is a substrate of sarcosine oxidase (alson known as N-methyl-L-tryptophan oxidase) which catalyzes the oxidative demethylation of sarcosine in the following reaction: Sarcosine + H2O + O2 = glycine + formaldehyde + H2O2 (methylamino)-Acetate (methylamino)-Acetic acid (Methylamino)acetate (Methylamino)acetic acid (Methylamino)ethanoate (Methylamino)ethanoic acid <i>N</i>-methylglycine Methylamino)-Acetate Methylamino)-Acetic acid Methylglycine N-Methyl-Glycine N-Methylaminoacetate N-Methylaminoacetic acid N-Methylglycine Sarcosin Sarcosinate Sarcosine Sarcosinic acid C3H7NO2 89.0932 89.047678473 2-(methylamino)acetic acid sarcosine 107-97-1 CNCC(O)=O InChI=1S/C3H7NO2/c1-4-2-3(5)6/h4H,2H2,1H3,(H,5,6) FSYKKLYZXJSNPZ-UHFFFAOYSA-N Solid Cytosol logp -3.06 ALOGPS logs 0.54 ALOGPS solubility 3.08e+02 g/l ALOGPS melting_point 208 oC logp -3.2 ChemAxon pka_strongest_acidic 2.06 ChemAxon pka_strongest_basic 10.35 ChemAxon iupac 2-(methylamino)acetic acid ChemAxon average_mass 89.0932 ChemAxon mono_mass 89.047678473 ChemAxon smiles CNCC(O)=O ChemAxon formula C3H7NO2 ChemAxon inchi InChI=1S/C3H7NO2/c1-4-2-3(5)6/h4H,2H2,1H3,(H,5,6) ChemAxon inchikey FSYKKLYZXJSNPZ-UHFFFAOYSA-N ChemAxon polar_surface_area 49.33 ChemAxon refractivity 20.78 ChemAxon polarizability 8.66 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Arginine and proline metabolism ec00330 Glycine, serine and threonine metabolism ec00260 Specdb::CMs 507 Specdb::CMs 508 Specdb::CMs 923 Specdb::CMs 20878 Specdb::CMs 30021 Specdb::CMs 30687 Specdb::CMs 30860 Specdb::CMs 31110 Specdb::CMs 32285 Specdb::CMs 37395 Specdb::CMs 146150 Specdb::CMs 1056496 Specdb::CMs 1056497 Specdb::CMs 1056499 Specdb::EiMs 880 Specdb::NmrOneD 1224 Specdb::NmrOneD 1307 Specdb::NmrOneD 2114 Specdb::NmrOneD 2807 Specdb::NmrOneD 143250 Specdb::NmrOneD 143251 Specdb::NmrOneD 143252 Specdb::NmrOneD 143253 Specdb::NmrOneD 143254 Specdb::NmrOneD 143255 Specdb::NmrOneD 143256 Specdb::NmrOneD 143257 Specdb::NmrOneD 143258 Specdb::NmrOneD 143259 Specdb::NmrOneD 143260 Specdb::NmrOneD 143261 Specdb::NmrOneD 143262 Specdb::NmrOneD 143263 Specdb::NmrOneD 143264 Specdb::NmrOneD 143265 Specdb::NmrOneD 143266 Specdb::NmrOneD 143267 Specdb::NmrOneD 143268 Specdb::NmrOneD 143269 Specdb::NmrOneD 166453 Specdb::MsMs 472 Specdb::MsMs 473 Specdb::MsMs 474 Specdb::MsMs 3885 Specdb::MsMs 3886 Specdb::MsMs 3887 Specdb::MsMs 3888 Specdb::MsMs 3889 Specdb::MsMs 3890 Specdb::MsMs 3891 Specdb::MsMs 3892 Specdb::MsMs 7130 Specdb::MsMs 7131 Specdb::MsMs 7132 Specdb::MsMs 13802 Specdb::MsMs 13803 Specdb::MsMs 13804 Specdb::MsMs 438428 Specdb::MsMs 438429 Specdb::MsMs 438430 Specdb::MsMs 446941 Specdb::MsMs 446942 Specdb::MsMs 446943 Specdb::MsMs 446944 Specdb::MsMs 446945 Specdb::NmrTwoD 1011 Specdb::NmrTwoD 1250 HMDB00271 1057 C00213 15611 SARCOSINE SAR Sarcosine 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 Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. 19212411 Shoemaker JD, Elliott WH: Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. J Chromatogr. 1991 Jan 2;562(1-2):125-38. 2026685 Silwood CJ, Lynch E, Claxson AW, Grootveld MC: 1H and (13)C NMR spectroscopic analysis of human saliva. J Dent Res. 2002 Jun;81(6):422-7. 12097436 Boulat O, Gradwohl M, Matos V, Guignard JP, Bachmann C: Organic acids in the second morning urine in a healthy Swiss paediatric population. Clin Chem Lab Med. 2003 Dec;41(12):1642-58. 14708889 Akare S, Martinez JD: Bile acid induces hydrophobicity-dependent membrane alterations. Biochim Biophys Acta. 2005 Jun 15;1735(1):59-67. 15951237 Lim DS, Roberts R, Marian AJ: Expression profiling of cardiac genes in human hypertrophic cardiomyopathy: insight into the pathogenesis of phenotypes. J Am Coll Cardiol. 2001 Oct;38(4):1175-80. 11583900 Bales JR, Sadler PJ, Nicholson JK, Timbrell JA: Urinary excretion of acetaminophen and its metabolites as studied by proton NMR spectroscopy. Clin Chem. 1984 Oct;30(10):1631-6. 6206966 Heil M, Podebrad F, Prado E, Beck T, Mosand A, Sewell AC, Bohles H, Lehnert W: Enantioselective analysis of ketone bodies in patients with beta-ketothiolase deficiency, medium-chain acyl coenzyme A dehydrogenase deficiency and ketonemic vomiting. J Chromatogr B Biomed Sci Appl. 2000 Mar 10;739(2):313-24. 10755375 Kang ES, Seyer J, Todd TA, Herrera C: Variability in the phenotypic expression of abnormal sarcosine metabolism in a family. Hum Genet. 1983;64(1):80-5. 6192074 Vallera DA, Todhunter DA, Kuroki DW, Shu Y, Sicheneder A, Chen H: A bispecific recombinant immunotoxin, DT2219, targeting human CD19 and CD22 receptors in a mouse xenograft model of B-cell leukemia/lymphoma. Clin Cancer Res. 2005 May 15;11(10):3879-88. 15897589 Hitomi J, Yamaguchi K, Kikuchi Y, Kimura T, Maruyama K, Nagasaki K: A novel calcium-binding protein in amniotic fluid, CAAF1: its molecular cloning and tissue distribution. J Cell Sci. 1996 Apr;109 ( Pt 4):805-15. 8718672 Cipens, G.; Slavinska, V.; Sile, D.; Kreile, D.; Strautina, A.; Krikis, A.; Gutmanis, A. Synthesis of sarcosine and its use. Latvijas PSR Zinatnu Akademijas Vestis, Kimijas Serija (1986), (5), 515-24. http://hmdb.ca/system/metabolites/msds/000/000/199/original/HMDB00271.pdf?1358895585 N-methyl-L-tryptophan oxidase P40874 MTOX_ECOLI solA http://ecmdb.ca/proteins/P40874.xml Water + Oxygen + Sarcosine > Formaldehyde + Glycine + Hydrogen peroxide Luria-Bertani (LB) media Shake flask 33.2 uM true 6.0 37 oC BL21 DE3 Stationary phase cultures (overnight culture) 132800 24000 Lin, Z., Johnson, L. C., Weissbach, H., Brot, N., Lively, M. O., Lowther, W. T. (2007). "Free methionine-(R)-sulfoxide reductase from Escherichia coli reveals a new GAF domain function." Proc Natl Acad Sci U S A 104:9597-9602. 17535911 Luria-Bertani (LB) media Shake flask 32.17 uM true 2.01 37 oC BL21 DE3 Stationary phase cultures (overnight culture) 128667 8053 Lin, Z., Johnson, L. C., Weissbach, H., Brot, N., Lively, M. O., Lowther, W. T. (2007). "Free methionine-(R)-sulfoxide reductase from Escherichia coli reveals a new GAF domain function." Proc Natl Acad Sci U S A 104:9597-9602. 17535911