2.0 2012-10-10 12:19:23 -0600 2015-08-05 16:22:04 -0600 ECMDB23155 M2MDB003545 2-iminoacetate The 1,2-didehydro derivative of glycine 2-Iminoacetic acid Iminoacetate Iminoacetic acid Iminoglycine C2H3NO2 73.0507 73.016378345 2-iminoacetic acid iminoacetic acid OC(=O)C=N InChI=1S/C2H3NO2/c3-1-2(4)5/h1,3H,(H,4,5) TVMUHOAONWHJBV-UHFFFAOYSA-N logp -1.03 ALOGPS logs -1.05 ALOGPS solubility 6.46e+00 g/l ALOGPS logp -0.77 ChemAxon pka_strongest_acidic 3.93 ChemAxon pka_strongest_basic 3.27 ChemAxon iupac 2-iminoacetic acid ChemAxon average_mass 73.0507 ChemAxon mono_mass 73.016378345 ChemAxon smiles OC(=O)C=N ChemAxon formula C2H3NO2 ChemAxon inchi InChI=1S/C2H3NO2/c3-1-2(4)5/h1,3H,(H,4,5) ChemAxon inchikey TVMUHOAONWHJBV-UHFFFAOYSA-N ChemAxon polar_surface_area 61.15 ChemAxon refractivity 25.97 ChemAxon polarizability 5.88 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Thiamine metabolism ec00730 Metabolic pathways eco01100 tyrosine biosynthesis The pathways of biosynthesis of phenylalaline and tyrosine are intimately connected. First step of both pathways is the conversion of chorismate to prephenate, the third step of both is the conversion of a ketoacid to the aminoacid through transamination. The two pathways differ only in the second step of their three-step reaction sequences: In the case of phenylalanine biosynthesi a dehydratase converts prephenate to phenylpyruvate(reaction occurs slowly in the absence of enzymic activity); in the case of tyrosine biosynthesis, a dehydrogenase converts prephenate to p-hydroxyphenylpyruvate. Also in both pathways the first two steps are catalyzed by two distinc active sites on a single protein. Thus the first step of each pathway can be catalyzed by two enzyme: those associated with both the phenylalanine specific dehydratase and the tyrosine specific dehydrogenase. Three enzymes those enconde by tyrB, aspC and ilvE are involved in catalyzing the third step of these pathways, all three can contribute to the synthesis of phenylalanine: only tyrB and aspC contribute to biosynthesis of tyrosine PW000806 Metabolic Specdb::CMs 1085999 Specdb::MsMs 26399 Specdb::MsMs 26400 Specdb::MsMs 26401 Specdb::MsMs 32957 Specdb::MsMs 32958 Specdb::MsMs 32959 C15809 Thiazole synthase P30139 THIG_ECOLI thiG http://ecmdb.ca/proteins/P30139.xml Dehydroglycine synthase P30140 THIH_ECOLI thiH http://ecmdb.ca/proteins/P30140.xml 1-Deoxy-D-xylulose 5-phosphate + 2-iminoacetate + thiocarboxy-adenylate-[sulfur-carrier protein ThiS] > 2-((2R,5Z)-2-Carboxy-4-methylthiazol-5(2H)-ylidene)ethyl phosphate + [sulfur-carrier protein ThiS] +2 Water L-Tyrosine + S-adenosyl-L-methionine + reduced acceptor > 2-iminoacetate + p-Cresol + 5'-Deoxyadenosine + L-Methionine + acceptor +2 Hydrogen ion L-Tyrosine + S-Adenosylmethionine + NADPH <> 2-iminoacetate + p-Cresol + 5'-Deoxyadenosine + L-Methionine + NADP + Hydrogen ion R10246 1-Deoxy-D-xylulose 5-phosphate + 2-iminoacetate <> 2-[(2R,5Z)-2-Carboxy-4-methylthiazol-5(2H)-ylidene]ethyl phosphate +2 Water R10247 L-Tyrosine + NADPH + S-adenosyl-L-methionine + L-Tyrosine + NADPH > Hydrogen ion + NADP + L-Methionine + 5'-Deoxyadenosine + p-Cresol + 2-iminoacetate PW_R005174 C15815 + L-Tyrosine + 2-iminoacetate <>4 4-Methyl-5-(2-phosphoethyl)-thiazole 1-Deoxy-D-xylulose 5-phosphate + 2 2-iminoacetate <>2 2-[(2R,5Z)-2-Carboxy-4-methylthiazol-5(2H)-ylidene]ethyl phosphate +2 Water C15815 + L-Tyrosine + 2-iminoacetate <>4 4-Methyl-5-(2-phosphoethyl)-thiazole