2.0 2012-05-31 13:52:33 -0600 2015-09-13 12:56:11 -0600 ECMDB01432 M2MDB000385 Agmatine Agmatine (also known as (4-aminobutyl)guanidine) is the decarboxylation product of the amino acid arginine and is an intermediate in polyamine biosynthesis. (Wikipedia) In E. coli arginine metabolism, agmatine is produced from arginine in a reaction catalyzed by arginine decarboxylase (4.1.1.19). Another enzyme, agmatinase (EC 3.5.3.11), can then convert agmatine to putrescine, which is a polyamine that can be further converted to other products such as spermidine. (KEGG) (4-aminobutyl)-Guanidine (4-Aminobutyl)guanidine 1-(4-Aminobutyl)guanidine 1-Amino-4-guanidinobutane 1-Amino-4-guanidobutane 4-Guanidino-1-butanamine Agmatine Argmatine N-(4-Aminobutyl)guanidine N-(Aminoiminomethyl)-1,4-Butanediamine N-4-Aminobutylguanidine C5H14N4 130.1915 130.121846468 N-(4-aminobutyl)guanidine agmatine 306-60-5 NCCCCNC(N)=N InChI=1S/C5H14N4/c6-3-1-2-4-9-5(7)8/h1-4,6H2,(H4,7,8,9) QYPPJABKJHAVHS-UHFFFAOYSA-N Solid Cytosol Extra-organism Periplasm logp -1.01 ALOGPS logs -1.56 ALOGPS solubility 3.61e+00 g/l ALOGPS logp -1.2 ChemAxon pka_strongest_basic 12.61 ChemAxon iupac N-(4-aminobutyl)guanidine ChemAxon average_mass 130.1915 ChemAxon mono_mass 130.121846468 ChemAxon smiles NCCCCNC(N)=N ChemAxon formula C5H14N4 ChemAxon inchi InChI=1S/C5H14N4/c6-3-1-2-4-9-5(7)8/h1-4,6H2,(H4,7,8,9) ChemAxon inchikey QYPPJABKJHAVHS-UHFFFAOYSA-N ChemAxon polar_surface_area 87.92 ChemAxon refractivity 48.09 ChemAxon polarizability 15.01 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 4 ChemAxon donor_count 4 ChemAxon physiological_charge 2 ChemAxon formal_charge 0 ChemAxon Arginine and proline metabolism ec00330 Metabolic pathways eco01100 arginine metabolism The metabolism of L-arginine starts with the acetylation of L-glutamic acid resulting in a N-acetylglutamic acid while releasing a coenzyme A and a hydrogen ion. N-acetylglutamic acid is then phosphorylated via an ATP driven acetylglutamate kinase which yields a N-acetyl-L-glutamyl 5-phosphate. This compound undergoes a NDPH dependent reduction resulting in N-acetyl-L-glutamate 5-semialdehyde. This compound reacts with L-glutamic acid through a acetylornithine aminotransferase / N-succinyldiaminopimelate aminotransferase to produce a N-acetylornithine which is then deacetylated through a acetylornithine deacetylase which yield an ornithine. L-glutamine is used to synthesize carbamoyl phosphate through the interaction of L-glutamine, water, ATP, and hydrogen carbonate. This reaction yields ADP, L-glutamic acid, phosphate, and hydrogen ion. Carbamoyl phosphate and ornithine are used to catalyze the production of citrulline through an ornithine carbamoyltransferase. Citrulline reacts with L-aspartic acid through an ATP dependent enzyme, argininosuccinate synthase to produce pyrophosphate, AMP and argininosuccinic acid. Argininosussinic acid is then lyase to produce L-arginine and fumaric acid. L-arginine can be metabolized into succinic acid by two different sets of reactions: 1. Arginine reacts with succinyl-CoA through a arginine N-succinyltransferase resulting in N2-succinyl-L-arginine while releasing CoA and Hydrogen Ion. N2-succinyl-L-arginine is then dihydrolase to produce a N2-succinyl-L-ornithine through a N-succinylarginine dihydrolase. This compound in turn reacts with oxoglutaric acid through succinylornithine transaminase resulting in L-glutamic acid and N2-succinyl-L-glutamic acid 5-semialdehyde. This compoud in turn reacts with a NAD dependent dehydrogenase resulting in N2-succinylglutamate while releasing NADH and hydrogen ion. N2-succinylglutamate reacts with water through a succinylglutamate desuccinylase resulting in L-glutamic acid and a succinic acid. The succinic acid is then incorporated in the TCA cycle 2.Argine reacts with carbon dioxide and a hydrogen ion through a biodegradative arginine decarboxylase, resulting in Agmatine. This compound is then transformed into putrescine by reacting with water and an agmatinase, and releasing urea. Putrescine can be metabolized by reaction with either l-glutamic acid or oxoglutaric acid. If putrescine reacts with L-glutamic acid, it reacts through an ATP mediated gamma-glutamylputrescine producing a hydrogen ion, ADP, phosphate and gamma-glutamyl-L-putrescine. This compound is reduced by interacting with oxygen, water and a gamma-glutamylputrescine oxidoreductase resulting in ammonium, hydrogen peroxide and 4-gamma-glutamylamino butanal. This compound is dehydrogenated through a NADP mediated reaction lead by gamma-glutamyl-gamma-aminobutaryaldehyde dehydrogenase resulting in hydrogen ion, NADPH and 4-glutamylamino butanoate. In turn, the latter compound reacts with water through a gamma-glutamyl-gamma-aminobutyrate hydrolase resulting in L-glutamic acid and Gamma aminobutyric acid. On the other hand, if putrescine reacts with oxoglutaric acid through a putrescine aminotransferase, it results in L-glutamic acid, and a 4-aminobutyraldehyde. This compound reacts with water through a NAD dependent gamma aminobutyraldehyde dehydrogenase resulting in hydrogen ion, NADH and gamma-aminobutyric acid. Gamma Aaminobutyric acid reacts with oxoglutaric acid through 4-aminobutyrate aminotransferase resulting in L-glutamic acid and succinic acid semialdehyde. This compound in turn can react with with either NADP or NAD to result in the production of succinic acid through succinate-semialdehyde dehydrogenase or aldehyde dehydrogenase-like protein yneI respectively. Succinic acid can then be integrated in the TCA cycle. L-arginine is eventua lly metabolized into succinic acid which then goes to the TCA cycle PW000790 Metabolic arginine degradation III (arginine decarboxylase/agmatinase pathway) PWY0-823 putrescine biosynthesis I PWY-40 arginine dependent acid resistance PWY0-1299 Specdb::CMs 751 Specdb::CMs 752 Specdb::CMs 1399 Specdb::CMs 5906 Specdb::CMs 31334 Specdb::CMs 31686 Specdb::CMs 148603 Specdb::NmrOneD 1706 Specdb::NmrOneD 9322 Specdb::NmrOneD 9323 Specdb::NmrOneD 9324 Specdb::NmrOneD 9325 Specdb::NmrOneD 9326 Specdb::NmrOneD 9327 Specdb::NmrOneD 9328 Specdb::NmrOneD 9329 Specdb::NmrOneD 9330 Specdb::NmrOneD 9331 Specdb::NmrOneD 9332 Specdb::NmrOneD 9333 Specdb::NmrOneD 9334 Specdb::NmrOneD 9335 Specdb::NmrOneD 9336 Specdb::NmrOneD 9337 Specdb::NmrOneD 9338 Specdb::NmrOneD 9339 Specdb::NmrOneD 9340 Specdb::NmrOneD 9341 Specdb::NmrOneD 166611 Specdb::MsMs 1577 Specdb::MsMs 1578 Specdb::MsMs 1579 Specdb::MsMs 5313 Specdb::MsMs 5314 Specdb::MsMs 5315 Specdb::MsMs 5316 Specdb::MsMs 5317 Specdb::MsMs 5320 Specdb::MsMs 5321 Specdb::MsMs 21335 Specdb::MsMs 21336 Specdb::MsMs 21337 Specdb::MsMs 22886 Specdb::MsMs 22887 Specdb::MsMs 22888 Specdb::MsMs 441451 Specdb::MsMs 445666 Specdb::MsMs 445667 Specdb::MsMs 445668 Specdb::MsMs 445669 Specdb::MsMs 445670 Specdb::MsMs 447959 Specdb::MsMs 448128 Specdb::MsMs 451914 Specdb::NmrTwoD 1072 Specdb::NmrTwoD 1647 HMDB01432 199 194 C00179 17431 AGMATHINE AG2 Agmatine Keseler, I. 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Epub 2006 Jul 3. 16820162 http://hmdb.ca/system/metabolites/msds/000/001/294/original/HMDB01432.pdf?1358462635 Biosynthetic arginine decarboxylase P21170 SPEA_ECOLI speA http://ecmdb.ca/proteins/P21170.xml Biodegradative arginine decarboxylase P28629 ADIA_ECOLI adiA http://ecmdb.ca/proteins/P28629.xml Agmatinase P60651 SPEB_ECOLI speB http://ecmdb.ca/proteins/P60651.xml Outer membrane protein N P77747 OMPN_ECOLI ompN http://ecmdb.ca/proteins/P77747.xml Outer membrane pore protein E P02932 PHOE_ECOLI phoE http://ecmdb.ca/proteins/P02932.xml Arginine/agmatine antiporter P60061 ADIC_ECOLI adiC http://ecmdb.ca/proteins/P60061.xml Outer membrane protein F P02931 OMPF_ECOLI ompF http://ecmdb.ca/proteins/P02931.xml Outer membrane protein C P06996 OMPC_ECOLI ompC http://ecmdb.ca/proteins/P06996.xml Agmatine + Water <> Putrescine + Urea + Ethylenediamine R01157 AGMATIN-RXN L-Arginine + Hydrogen ion <> Agmatine + Carbon dioxide R00566 ARGDECARBOX-RXN L-Arginine + Hydrogen ion > Agmatine + Carbon dioxide L-Arginine <> Agmatine + Carbon dioxide R00566 Agmatine + Water <> Putrescine + Urea R01157 Water + Agmatine > Urea + Putrescine AGMATIN-RXN L-Arginine > Agmatine + Carbon dioxide L-Arginine + Hydrogen ion + Carbon dioxide > Agmatine PW_R002683 L-Arginine + Hydrogen ion <> Agmatine + Carbon dioxide L-Arginine + Hydrogen ion <> Agmatine + Carbon dioxide 199 Medium with Earle’s salts –which contains 21 amino acids, 17 vitamins, 10 components of nucleic acids, sodium acetate, glucose, NaC1, KCl, CaC12, MgS04, Na2HP04, and Fe(N03)3 Shake flask 10.0 uM 0.0 37 oC K12 HB101 Mid Log Phase 40000 0 Hamana, K. (1996). "Distribution of diaminopropane and acetylspermidine in Enterobacteriaceae." Can J Microbiol 42:107-114. 8742354 199 Medium with Earle’s salts –which contains 21 amino acids, 17 vitamins, 10 components of nucleic acids, sodium acetate, glucose, NaC1, KCl, CaC12, MgS04, Na2HP04, and Fe(N03)3 Shake flask 110.0 uM 0.0 37 oC K12 HB101 Stationary Phase 440000 0 Hamana, K. (1996). "Distribution of diaminopropane and acetylspermidine in Enterobacteriaceae." Can J Microbiol 42:107-114. 8742354