2.02012-08-09 09:25:08 -06002015-06-03 17:21:39 -0600ECMDB21497M2MDB0018924-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-arabinopyranoseUDP-4-Amino-4-deoxy-beta-L-arabinopyranoseUDP-4-Amino-4-deoxy-L-arabinoseUDP-4-amino-4-Deoxy-β-L-arabinopyranoseUDP-Ara4NUDP-L-Ara4NC14H23N3O15P2535.291535.060440105[({[(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])OInChI=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/s1GWBAKYBSWHQNMQ-IAZOVDBXSA-NCytoplasmlogp-1.82logs-1.42solubility2.05e+01 g/llogp-5.3pka_strongest_acidic1.73pka_strongest_basic8.84iupac[({[(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 acidaverage_mass535.291mono_mass535.060440105smiles[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])OformulaC14H23N3O15P2inchiInChI=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/s1inchikeyGWBAKYBSWHQNMQ-IAZOVDBXSA-Npolar_surface_area280.59refractivity102.47polarizability43.73rotatable_bond_count8acceptor_count14donor_count8physiological_charge-1formal_charge0One Carbon Pool by Folate IDihydrofolic 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.
PW001735MetabolicSpecdb::CMs1083294Specdb::NmrOneD275538Specdb::NmrOneD275539Specdb::NmrOneD275540Specdb::NmrOneD275541Specdb::NmrOneD275542Specdb::NmrOneD275543Specdb::NmrOneD275544Specdb::NmrOneD275545Specdb::NmrOneD275546Specdb::NmrOneD275547Specdb::NmrOneD275548Specdb::NmrOneD275549Specdb::NmrOneD275550Specdb::NmrOneD275551Specdb::NmrOneD275552Specdb::NmrOneD275553Specdb::NmrOneD275554Specdb::NmrOneD275555Specdb::NmrOneD275556Specdb::NmrOneD275557Specdb::MsMs27548Specdb::MsMs27549Specdb::MsMs27550Specdb::MsMs34106Specdb::MsMs34107Specdb::MsMs341081775676921865443C16153van 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 370:17-25.17765195Winder, 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 80:2939-2948.18331064Bifunctional polymyxin resistance protein ArnAP77398ARNA_ECOLIarnAhttp://ecmdb.ca/proteins/P77398.xmlUDP-4-amino-4-deoxy-L-arabinose--oxoglutarate aminotransferaseP77690ARNB_ECOLIarnBhttp://ecmdb.ca/proteins/P77690.xmlUndecaprenyl phosphate-alpha-4-amino-4-deoxy-L-arabinose arabinosyl transferaseP76473ARNT_ECOLIarnThttp://ecmdb.ca/proteins/P76473.xmlN10-Formyl-THF + 4-Amino-4-deoxy-L-arabinose > Tetrahydrofolic acid + UDP-4-Deoxy-4-formamido-beta-L-arabinose4-Amino-4-deoxy-L-arabinose + Oxoglutaric acid > UDP-beta-L-Threo-pentapyranos-4-ulose + DL-Glutamic acid