2.0 2012-07-30 14:55:19 -0600 2015-06-03 17:21:10 -0600 ECMDB21328 M2MDB001730 Dehydroglycine Dehydroglycine is a member of the chemical class known as Alpha Amino Acids and Derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).Dehydroglycine is catalyzed by ThiH. ThiH is a tyrosine lyase that cleaves the C alpha-C beta bond of tyrosine, generating p-cresol as a by-product, to form dehydroglycine. (PMID 19923213) 2-Iminoacetate 2-Iminoacetic acid Dehydroglycine Iminoacetate Iminoacetic acid C2H2NO2 72.0428 72.008553313 2-iminoacetate 2-iminoacetate [O-]C(=O)C=N InChI=1S/C2H3NO2/c3-1-2(4)5/h1,3H,(H,4,5)/p-1 TVMUHOAONWHJBV-UHFFFAOYSA-M Cytosol logp -0.94 ALOGPS logs -0.98 ALOGPS solubility 9.41e+00 g/l ALOGPS logp -0.77 ChemAxon pka_strongest_acidic 3.93 ChemAxon pka_strongest_basic 3.27 ChemAxon iupac 2-iminoacetate ChemAxon average_mass 72.0428 ChemAxon mono_mass 72.008553313 ChemAxon smiles [O-]C(=O)C=N ChemAxon formula C2H2NO2 ChemAxon inchi InChI=1S/C2H3NO2/c3-1-2(4)5/h1,3H,(H,4,5)/p-1 ChemAxon inchikey TVMUHOAONWHJBV-UHFFFAOYSA-M ChemAxon polar_surface_area 63.98 ChemAxon refractivity 36.81 ChemAxon polarizability 5.49 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 3 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge -1 ChemAxon Thiazole Biosynthesis I This pathway describes only the synthesis of the thiazole moiety of thiamin. Different variations of this pathway exist, this particular pathway describes the pathway that occurs in Escherichia coli K-12 and Salmonella enterica enterica serovar Typhimurium. The biosynthesis of the thiazole moiety is complex. In Escherichia coli it involves six proteins, the products of the thiS, thiF, thiG, thiH, thiI, and iscS genes. The process begins when IscS, a protein that is also involved in the biosynthesis of iron-sulfur clusters, catalyzes the transfer of a sulfur atom from cysteine to a ThiI sulfur-carrier protein, generating a an S-sulfanyl-[ThiI sulfur-carrier protein]. In a parallel route, the ThiF protein activates a ThiS sulfur-carrier protein by adenylation of its carboxy terminus, generating a carboxy-adenylated-[ThiS sulfur-carrier protein]. In a second reaction, which may also be catalyzed by ThiF, the sulfur from an S-sulfanyl-[ThiI sulfur-carrier protein] is transferred to ThiS, generating a thiocarboxy-[ThiS-Protein]. The final reaction of this pathway, which is catalyzed by the ThiG protein, requires three inputs: a thiocarboxy-[ThiS-Protein], 1-deoxy-D-xylulose 5-phosphate and 2-iminoacetate. 2-iminoacetate is formed in Escherichia coli from L-tyrosine by tyrosine lyase (ThiH), which forms a complex with ThiG. For many years the products of this reaction was assumed to be 4-methyl-5-(β-hydroxyethyl)thiazole (thiazole). However, recent work performed with the thiazole synthase from Bacillus subtilis has shown that the actual product is the thiazole tautomer 2-[(2R,5Z)-(2-carboxy-4-methylthiazol-5(2H)-ylidene]ethyl phosphate. While in Bacillus a dedicated thiazole tautomerase converts this product into a different tautomer (2-(2-carboxy-4-methylthiazol-5-yl)ethyl phosphate), most of the proteobacteria lack the tautomerase. (EcoCyc) PW002041 Metabolic thiazole biosynthesis I (E. coli) PWY-6892 Specdb::MsMs 28904 Specdb::MsMs 28905 Specdb::MsMs 28906 Specdb::MsMs 35462 Specdb::MsMs 35463 Specdb::MsMs 35464 23347814 15272272 53664 CPD-12279 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 Challand, M. R., Martins, F. T., Roach, P. L. (2010). "Catalytic activity of the anaerobic tyrosine lyase required for thiamine biosynthesis in Escherichia coli." J Biol Chem 285:5240-5248. 19923213 Cysteine desulfurase P0A6B7 ISCS_ECOLI iscS http://ecmdb.ca/proteins/P0A6B7.xml Sulfur carrier protein ThiS adenylyltransferase P30138 THIF_ECOLI thiF http://ecmdb.ca/proteins/P30138.xml tRNA sulfurtransferase P77718 THII_ECOLI thiI http://ecmdb.ca/proteins/P77718.xml Thiazole synthase P30139 THIG_ECOLI thiG http://ecmdb.ca/proteins/P30139.xml Sulfur carrier protein ThiS O32583 THIS_ECOLI thiS http://ecmdb.ca/proteins/O32583.xml Dehydroglycine synthase P30140 THIH_ECOLI thiH http://ecmdb.ca/proteins/P30140.xml Adenosine triphosphate + Dehydroglycine + 1-Deoxy-D-xylulose 5-phosphate + Hydrogen ion + IscS with bound sulfur + NADPH > 4-Methyl-5-(2-phosphoethyl)-thiazole + Adenosine monophosphate + Carbon dioxide +2 Water + IscS sulfur acceptor protein + NADP + Pyrophosphate S-Adenosylmethionine + NADPH + L-Tyrosine > p-Cresol + 5'-Deoxyadenosine + Dehydroglycine + Hydrogen ion + L-Methionine + NADP Dehydroglycine + Water > Glyoxylic acid + Ammonia RXN-13329 L-Tyrosine + S-Adenosylmethionine + a reduced electron acceptor > Dehydroglycine + p-Cresol + 5'-Deoxyadenosine + L-Methionine + an oxidized electron acceptor + Hydrogen ion RXN-11319 1-Deoxy-D-xylulose 5-phosphate + Dehydroglycine + a thiocarboxy-[ThiS-Protein] > 2-((2R,5Z)-2-Carboxy-4-methylthiazol-5(2H)-ylidene)ethyl phosphate + a ThiS sulfur-carrier protein +2 Water PW_R005964 L-Tyrosine + S-adenosyl-L-methionine + NADPH > Dehydroglycine + 4-Methylcatechol + 5'-Deoxyadenosine + L-Methionine + NADP + Hydrogen ion PW_R005962