2.02012-05-31 14:32:20 -06002015-06-03 17:19:30 -0600ECMDB20191M2MDB001037Salicin 6-phosphateSalicin 6-phosphate is a sugar phosphate, derived from salicin which is an alcoholic beta-glucoside.. It is generated when salicin is transported from the periplasmic space into the cytoplasm by the CelT protein The reaction is as follows: phosphoenolpyruvate + salicin[periplasmic space] ¡ú salicin-6-phosphate[cytosol] + pyruvate. Salicin 6-phosphate is s substrate for CelF. CelF has been shown to hydrolyze a variety of P-beta-glucosides, including cellobiose-6P, salicin-6P, arbutin-6P, gentiobiose-6P and methyl-beta-glucoside-6P. (PMID:10572139)Salicin 6-phosphoric acidSalicin-6-pSalicin-6P[3,4,5-trihydroxy-6-[2-(hydroxymethyl)phenoxy]-tetrahydropyran-2-yl]methoxyphosphonate[3,4,5-trihydroxy-6-[2-(hydroxymethyl)phenoxy]-tetrahydropyran-2-yl]methoxyphosphonic acidC13H19O10P366.2577366.07158334{[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[2-(hydroxymethyl)phenoxy]oxan-2-yl]methoxy}phosphonic acidsalicin-6P[H][C@]1(COP(O)(O)=O)O[C@@]([H])(OC2=CC=CC=C2CO)[C@]([H])(O)[C@@]([H])(O)[C@]1([H])OInChI=1S/C13H19O10P/c14-5-7-3-1-2-4-8(7)22-13-12(17)11(16)10(15)9(23-13)6-21-24(18,19)20/h1-4,9-17H,5-6H2,(H2,18,19,20)/t9-,10-,11+,12-,13-/m1/s1FSJKOMDYZYBBLV-UJPOAAIJSA-NCytoplasmPeriplasmlogp-1.41logs-1.57solubility9.90e+00 g/llogp-1.5pka_strongest_acidic1.22pka_strongest_basic-2.9iupac{[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[2-(hydroxymethyl)phenoxy]oxan-2-yl]methoxy}phosphonic acidaverage_mass366.2577mono_mass366.07158334smiles[H][C@]1(COP(O)(O)=O)O[C@@]([H])(OC2=CC=CC=C2CO)[C@]([H])(O)[C@@]([H])(O)[C@]1([H])OformulaC13H19O10PinchiInChI=1S/C13H19O10P/c14-5-7-3-1-2-4-8(7)22-13-12(17)11(16)10(15)9(23-13)6-21-24(18,19)20/h1-4,9-17H,5-6H2,(H2,18,19,20)/t9-,10-,11+,12-,13-/m1/s1inchikeyFSJKOMDYZYBBLV-UJPOAAIJSA-Npolar_surface_area166.14refractivity77.87polarizability32.21rotatable_bond_count6acceptor_count9donor_count6physiological_charge-2formal_charge0Glycolysis / Gluconeogenesisec00010Phosphotransferase system (PTS)ec02060Amino sugar and nucleotide sugar metabolism IIIThe synthesis of amino sugars and nucleotide sugars starts with the phosphorylation of N-Acetylmuramic acid (MurNac) through its transport from the periplasmic space to the cytoplasm. Once in the cytoplasm, MurNac and water undergo a reversible reaction through a N-acetylmuramic acid 6-phosphate etherase, producing a D-lactic acid and N-Acetyl-D-Glucosamine 6-phosphate. This latter compound can also be introduced into the cytoplasm through a phosphorylating PTS permase in the inner membrane that allows for the transport of N-Acetyl-D-glucosamine from the periplasmic space. N-Acetyl-D-Glucosamine 6-phosphate can also be obtained from chitin dependent reactions. Chitin is hydrated through a bifunctional chitinase to produce chitobiose. This in turn gets hydrated by a beta-hexosaminidase to produce N-acetyl-D-glucosamine. The latter undergoes an atp dependent phosphorylation leading to the production of N-Acetyl-D-Glucosamine 6-phosphate.
N-Acetyl-D-Glucosamine 6-phosphate is then be deacetylated in order to produce Glucosamine 6-phosphate through a N-acetylglucosamine-6-phosphate deacetylase. This compound is then deaminased into Beta-D-fructofuranose 6-phosphate through a glucosamine-6-phosphate deaminase.
Beta-D-fructofuranose 6-phosphate is isomerized into a beta-D-glucose 6-phosphate through a glucose-6-phosphate isomerase. The compound is then isomerized by a putative beta-phosphoglucomutase to produce a beta-D-glucose 1-phosphate. This compound enters the nucleotide sugar metabolism through uridylation resulting in a UDP-glucose. UDP-glucose is then dehydrated through a UDP-glucose 6-dehydrogenase to produce a UDP-glucuronic acid. This compound undergoes a NAD dependent reaction through a bifunctional polymyxin resistance protein to produce UDP-Beta-L-threo-pentapyranos-4-ulose. This compound then reacts with L-glutamic acid through a UDP-4-amino-4-deoxy-L-arabinose--oxoglutarate aminotransferase to produce an oxoglutaric acid and UDP-4-amino-4-deoxy-beta-L-arabinopyranose
The latter compound interacts with a N10-formyl-tetrahydrofolate through a bifunctional polymyxin resistance protein ArnA, resulting in a tetrahydrofolate, a hydrogen ion and a UDP-4-deoxy-4-formamido-beta-L-arabinopyranose, which in turn reacts with a product of the methylerythritol phosphate and polysoprenoid biosynthesis pathway, di-trans,octa-cis-undecaprenyl phosphate to produce a 4-deoxy-4-formamido-alpha-L-arabinopyranosyl ditrans, octacis-undecaprenyl phosphate.
Alpha-D-glucose is introduced into the cytoplasm through a glucose PTS permease, which phosphorylates the compound in order to produce an alpha-D-glucose 6-phosphate. This compound is then modified through a phosphoglucomutase 1 to yield alpha-D-glucose 1-phosphate. This compound can either be adenylated to produce ADP-glucose or uridylylated to produce galactose 1-phosphate through glucose-1-phosphate adenyllyltransferase and galactose-1-phosphate uridylyltransferase respectively.PW000895MetabolicSpecdb::CMs1084574Specdb::NmrOneD291435Specdb::NmrOneD291436Specdb::NmrOneD291437Specdb::NmrOneD291438Specdb::NmrOneD291439Specdb::NmrOneD291440Specdb::NmrOneD291441Specdb::NmrOneD291442Specdb::NmrOneD291443Specdb::NmrOneD291444Specdb::NmrOneD291445Specdb::NmrOneD291446Specdb::NmrOneD291447Specdb::NmrOneD291448Specdb::NmrOneD291449Specdb::NmrOneD291450Specdb::NmrOneD291451Specdb::NmrOneD291452Specdb::NmrOneD291453Specdb::NmrOneD291454Specdb::MsMs29465Specdb::MsMs29466Specdb::MsMs29467Specdb::MsMs36023Specdb::MsMs36024Specdb::MsMs36025440938389767C061889003CPD-1181P53Keseler, 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-D590.21097882Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114.220805106-phospho-beta-glucosidase BglBP11988BGLB_ECOLIbglBhttp://ecmdb.ca/proteins/P11988.xml6-phospho-beta-glucosidase AscBP24240ASCB_ECOLIascBhttp://ecmdb.ca/proteins/P24240.xmlPTS system arbutin-, cellobiose-, and salicin-specific EIIBC componentP24241PTIBC_ECOLIascFhttp://ecmdb.ca/proteins/P24241.xmlGlucose-specific phosphotransferase enzyme IIA componentP69783PTGA_ECOLIcrrhttp://ecmdb.ca/proteins/P69783.xml6-phospho-beta-glucosidase BglAQ46829BGLA_ECOLIbglAhttp://ecmdb.ca/proteins/Q46829.xmlPTS system arbutin-, cellobiose-, and salicin-specific EIIBC componentP24241PTIBC_ECOLIascFhttp://ecmdb.ca/proteins/P24241.xmlProtein N(pi)-phospho-L-histidine + Salicin <> Protein histidine + Salicin 6-phosphateR04394Salicin 6-phosphate + Water <> Salicyl alcohol + beta-D-Glucose 6-phosphateR05134Salicin 6-phosphate + Water > Glucose 6-phosphate + salicyl alcoholRXN0-5297Phosphoenolpyruvic acid + Salicin > Salicin 6-phosphate + Pyruvic acidTRANS-RXN-153ASalicin 6-phosphate + Water > β-D-glucose 1-phosphate + Salicyl alcoholPW_R005875