2.0 2012-08-09 09:25:08 -0600 2015-06-03 17:21:39 -0600 ECMDB21497 M2MDB001892 4-Amino-4-deoxy-L-arabinose 4-amino-4-deoxy-L-arabinose is invovled in Modification of lipid A. Attachment of the cationic sugar 4-amino-4-deoxy-l-arabinose (l-Ara4N) to lipid A is required for the maintenance of polymyxin resistance in Escherichia coli. The enzyme called AmT synthesizes this molecule and transfers it to lipid A. UDP-4-amino-4-Deoxy-b-L-arabinopyranose UDP-4-Amino-4-deoxy-beta-L-arabinopyranose UDP-4-Amino-4-deoxy-L-arabinose UDP-4-amino-4-Deoxy-β-L-arabinopyranose UDP-Ara4N UDP-L-Ara4N C14H23N3O15P2 535.291 535.060440105 [({[(2R,3R,4S,5S)-5-amino-3,4-dihydroxyoxan-2-yl]oxy}(hydroxy)phosphoryl)oxy]({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-hydroxy-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy})phosphinic acid {[(2R,3R,4S,5S)-5-amino-3,4-dihydroxyoxan-2-yl]oxy(hydroxy)phosphoryl}oxy[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-hydroxy-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxyphosphinic acid [H][C@]1(COP(O)(=O)OP(O)(=O)O[C@@]2([H])OC[C@]([H])(N)[C@]([H])(O)[C@@]2([H])O)O[C@@]([H])(N2C=CC(O)=NC2=O)[C@]([H])(O)[C@]1([H])O InChI=1S/C14H23N3O15P2/c15-5-3-28-13(11(22)8(5)19)31-34(26,27)32-33(24,25)29-4-6-9(20)10(21)12(30-6)17-2-1-7(18)16-14(17)23/h1-2,5-6,8-13,19-22H,3-4,15H2,(H,24,25)(H,26,27)(H,16,18,23)/t5-,6+,8-,9+,10+,11+,12+,13+/m0/s1 GWBAKYBSWHQNMQ-IAZOVDBXSA-N Cytoplasm logp -1.82 ALOGPS logs -1.42 ALOGPS solubility 2.05e+01 g/l ALOGPS logp -5.3 ChemAxon pka_strongest_acidic 1.73 ChemAxon pka_strongest_basic 8.84 ChemAxon iupac [({[(2R,3R,4S,5S)-5-amino-3,4-dihydroxyoxan-2-yl]oxy}(hydroxy)phosphoryl)oxy]({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-hydroxy-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy})phosphinic acid ChemAxon average_mass 535.291 ChemAxon mono_mass 535.060440105 ChemAxon smiles [H][C@]1(COP(O)(=O)OP(O)(=O)O[C@@]2([H])OC[C@]([H])(N)[C@]([H])(O)[C@@]2([H])O)O[C@@]([H])(N2C=CC(O)=NC2=O)[C@]([H])(O)[C@]1([H])O ChemAxon formula C14H23N3O15P2 ChemAxon inchi InChI=1S/C14H23N3O15P2/c15-5-3-28-13(11(22)8(5)19)31-34(26,27)32-33(24,25)29-4-6-9(20)10(21)12(30-6)17-2-1-7(18)16-14(17)23/h1-2,5-6,8-13,19-22H,3-4,15H2,(H,24,25)(H,26,27)(H,16,18,23)/t5-,6+,8-,9+,10+,11+,12+,13+/m0/s1 ChemAxon inchikey GWBAKYBSWHQNMQ-IAZOVDBXSA-N ChemAxon polar_surface_area 280.59 ChemAxon refractivity 102.47 ChemAxon polarizability 43.73 ChemAxon rotatable_bond_count 8 ChemAxon acceptor_count 14 ChemAxon donor_count 8 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon One Carbon Pool by Folate I Dihydrofolic acid, a product of the folate biosynthesis pathway, can be metabolized by multiple enzymes. Dihydrofolic acid can be reduced by a NADP-driven dihydrofolate reductase resulting in a NADPH, hydrogen ion and folic acid. Dihydrofolic acid can also be reduced by an NADPH-driven dihydrofolate reductase resulting in a NADP and a tetrahydrofolic acid. Folic acid can also produce a tetrahydrofolic acid through a NADPH-driven dihydrofolate reductase. Dihydrofolic acid also interacts with 5-thymidylic acid through a thymidylate synthase resulting in the release of dUMP and 5,10-methylene-THF Tetrahydrofolic acid can be converted into 5,10-methylene-THF through two different reversible reactions. Tetrahydrofolic acid interacts with a S-Aminomethyldihydrolipoylprotein through a aminomethyltransferase resulting in the release of ammonia, a dihydrolipoylprotein and 5,10-Methylene-THF Tetrahydrofolic acid interacts with L-serine through a glycine hydroxymethyltransferase resulting in a glycine, water and 5,10-Methylene-THF. The compound 5,10-methylene-THF reacts with an NADPH dependent methylenetetrahydrofolate reductase [NAD(P)H] resulting in NADP and 5-Methyltetrahydrofolic acid. This compound interacts with homocysteine through a methionine synthase resulting in L-methionine and tetrahydrofolic acid. Tetrahydrofolic acid can be metabolized into 10-formyltetrahydrofolate through 4 different enzymes: 1.- Tetrahydrofolic acid interacts with FAICAR through a phosphoribosylaminoimidazolecarboxamide formyltransferase resulting in a 1-(5'-Phosphoribosyl)-5-amino-4-imidazolecarboxamide and a 10-formyltetrahydrofolate 2.-Tetrahydrofolic acid interacts with 5'-Phosphoribosyl-N-formylglycinamide through a phosphoribosylglycinamide formyltransferase 2 resulting in a Glycineamideribotide and a 10-formyltetrahydrofolate 3.-Tetrahydrofolic acid interacts with Formic acid through a formyltetrahydrofolate hydrolase resulting in water and a 10-formyltetrahydrofolate 4.-Tetrahydrofolic acid interacts with N-formylmethionyl-tRNA(fMet) through a 10-formyltetrahydrofolate:L-methionyl-tRNA(fMet) N-formyltransferase resulting in a L-methionyl-tRNA(Met) and a 10-formyltetrahydrofolate 10-formyltetrahydrofolate can interact with a hydrogen ion through a bifunctional 5,10-methylene-tetrahydrofolate dehydrogenase resulting in water and 5,10-methenyltetrahydrofolic acid. Tetrahydrofolic acid can be metabolized into 5,10-methenyltetrahydrofolic acid by reacting with a 5'-phosphoribosyl-a-N-formylglycineamidine through a phosphoribosylglycinamide formyltransferase 2 resulting in water, glycineamideribotide and 5,10-methenyltetrahydrofolic acid. The latter compound can either interact with water through an aminomethyltransferase resulting in a N5-Formyl-THF, or it can interact with a NADPH driven bifunctional 5,10-methylene-tetrahydrofolate dehydrogenase resulting in a NADP and 5,10-Methylene THF. PW001735 Metabolic Specdb::CMs 1083294 Specdb::NmrOneD 275538 Specdb::NmrOneD 275539 Specdb::NmrOneD 275540 Specdb::NmrOneD 275541 Specdb::NmrOneD 275542 Specdb::NmrOneD 275543 Specdb::NmrOneD 275544 Specdb::NmrOneD 275545 Specdb::NmrOneD 275546 Specdb::NmrOneD 275547 Specdb::NmrOneD 275548 Specdb::NmrOneD 275549 Specdb::NmrOneD 275550 Specdb::NmrOneD 275551 Specdb::NmrOneD 275552 Specdb::NmrOneD 275553 Specdb::NmrOneD 275554 Specdb::NmrOneD 275555 Specdb::NmrOneD 275556 Specdb::NmrOneD 275557 Specdb::MsMs 27548 Specdb::MsMs 27549 Specdb::MsMs 27550 Specdb::MsMs 34106 Specdb::MsMs 34107 Specdb::MsMs 34108 17756769 21865443 C16153 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 Bifunctional polymyxin resistance protein ArnA P77398 ARNA_ECOLI arnA http://ecmdb.ca/proteins/P77398.xml UDP-4-amino-4-deoxy-L-arabinose--oxoglutarate aminotransferase P77690 ARNB_ECOLI arnB http://ecmdb.ca/proteins/P77690.xml Undecaprenyl phosphate-alpha-4-amino-4-deoxy-L-arabinose arabinosyl transferase P76473 ARNT_ECOLI arnT http://ecmdb.ca/proteins/P76473.xml N10-Formyl-THF + 4-Amino-4-deoxy-L-arabinose > Tetrahydrofolic acid + UDP-4-Deoxy-4-formamido-beta-L-arabinose 4-Amino-4-deoxy-L-arabinose + Oxoglutaric acid > UDP-beta-L-Threo-pentapyranos-4-ulose + DL-Glutamic acid