2.02012-05-31 13:44:41 -06002015-10-15 16:13:50 -0600ECMDB01078M2MDB000244Mannose 6-phosphateMannose-6-phosphate (M6P) is a molecule bound by lectin. M6P is converted to fructose 6-phosphate by mannose phosphate isomerase. (Wikipedia)α-D-mannose-6-Pα-D-mannose-6-phosphateα-D-mannose-6-phosphoric acida-D-Mannose-6-Pa-D-Mannose-6-phosphatea-D-Mannose-6-phosphoric acida-delta-Mannose-6-Pa-delta-Mannose-6-phosphatea-delta-Mannose-6-phosphoric acida-δ-Mannose-6-Pa-δ-Mannose-6-phosphatea-δ-Mannose-6-phosphoric acidAlpha-D-Mannose-6-PAlpha-D-Mannose-6-phosphatealpha-D-Mannose-6-phosphoric acidAlpha-delta-Mannose-6-PAlpha-delta-Mannose-6-phosphatealpha-delta-Mannose-6-phosphoric acidD-Mannose 6-phosphateD-Mannose 6-phosphoric acidDelta-Mannose 6-phosphatedelta-Mannose 6-phosphoric acidMan-6-pMan6PMannose 6-phosphateMannose 6-phosphoric acidMannose-6-phosphateMannose-6-phosphoric acidα-D-Mannose-6-Pα-D-Mannose-6-phosphateα-D-Mannose-6-phosphoric acidα-δ-Mannose-6-Pα-δ-Mannose-6-phosphateα-δ-Mannose-6-phosphoric acidδ-Mannose 6-phosphateδ-Mannose 6-phosphoric acidC6H13O9P260.1358260.029718526(3,4,5,6-tetrahydroxyoxan-2-yl)methyl phosphate(3,4,5,6-tetrahydroxyoxan-2-yl)methyl phosphate3672-15-9O[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@@H]1OInChI=1S/C6H13O9P/c7-3-2(1-14-16(11,12)13)15-6(10)5(9)4(3)8/h2-10H,1H2,(H2,11,12,13)/t2-,3-,4+,5+,6-/m1/s1NBSCHQHZLSJFNQ-RWOPYEJCSA-NSolidCytosolExtra-organismPeriplasmlogp-2.30logs-0.49solubility9.50e+01 g/llogp-3.1pka_strongest_acidic1.22pka_strongest_basic-3.6iupac(3,4,5,6-tetrahydroxyoxan-2-yl)methyl phosphateaverage_mass260.1358mono_mass260.029718526smilesO[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@@H]1OformulaC6H13O9PinchiInChI=1S/C6H13O9P/c7-3-2(1-14-16(11,12)13)15-6(10)5(9)4(3)8/h2-10H,1H2,(H2,11,12,13)/t2-,3-,4+,5+,6-/m1/s1inchikeyNBSCHQHZLSJFNQ-RWOPYEJCSA-Npolar_surface_area162.57refractivity44.55polarizability20.49rotatable_bond_count3acceptor_count8donor_count4physiological_charge-2formal_charge-2Fructose and mannose metabolismec00051Galactose metabolismGalactose can be synthesized through two pathways: melibiose degradation involving an alpha galactosidase and lactose degradation involving a beta galactosidase. Melibiose is first transported inside the cell through the melibiose:Li+/Na+/H+ symporter. Once inside the cell, melibiose is degraded through alpha galactosidase into an alpha-D-galactose and a beta-D-glucose. The beta-D-glucose is phosphorylated by a glucokinase to produce a beta-D-glucose-6-phosphate which can spontaneously be turned into a alpha D glucose 6 phosphate. This alpha D-glucose-6-phosphate is metabolized into a glucose -1-phosphate through a phosphoglucomutase-1. The glucose -1-phosphate is transformed into a uridine diphosphate glucose through UTP--glucose-1-phosphate uridylyltransferase. The product, uridine diphosphate glucose, can undergo a reversible reaction in which it can be turned into uridine diphosphategalactose through an UDP-glucose 4-epimerase.
Galactose can also be produced by lactose degradation involving a lactose permease to uptake lactose from the environment and a beta-galactosidase to turn lactose into Beta-D-galactose.
Beta-D-galactose can also be uptaken from the environment through a galactose proton symporter.
Galactose is degraded through the following process:
Beta-D-galactose is introduced into the cytoplasm through a galactose proton symporter, or it can be synthesized from an alpha lactose that is introduced into the cytoplasm through a lactose permease. Alpha lactose interacts with water through a beta-galactosidase resulting in a beta-D-glucose and beta-D-galactose. Beta-D-galactose is isomerized into D-galactose. D-Galactose undergoes phosphorylation through a galactokinase, hence producing galactose 1 phosphate. On the other side of the pathway, a gluose-1-phosphate (product of the interaction of alpha-D-glucose 6-phosphate with a phosphoglucomutase resulting in a alpha-D-glucose-1-phosphate, an isomer of Glucose 1-phosphate, or an isomer of Beta-D-glucose 1-phosphate) interacts with UTP and a hydrogen ion in order to produce a uridine diphosphate glucose. This is followed by the interaction of galactose-1-phosphate with an established amount of uridine diphosphate glucose through a galactose-1-phosphate uridylyltransferase, which in turn output a glucose-1-phosphate and a uridine diphosphate galactose. The glucose -1-phosphate is transformed into a uridine diphosphate glucose through UTP--glucose-1-phosphate uridylyltransferase. The product, uridine diphosphate glucose, can undergo a reversible reaction in which it can be turned into uridine diphosphategalactose through an UDP-glucose 4-epimerase, and so the cycle can keep going as long as more lactose or galactose is imported into the cell
PW000821ec00052MetabolicAmino sugar and nucleotide sugar metabolismec00520Phosphotransferase system (PTS)ec02060Metabolic pathwayseco01100Amino sugar and nucleotide sugar metabolism IIThe 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.
The beta-D-fructofuranose 6 -phosphate is isomerized in a reversible reaction into an alpha-D-mannose 6-phosphate. This compound can also be introduced into the cell from the periplasmic space through a mannose PTS permease that phosphorylates an alpha-D-mannose. Alpha-D-mannose 6-phosphate undergoes a reversible reaction through a phosphomannomutase to produce an alpha-D-mannose 1-phosphate.
The alpha-D-mannose 1-phosphate enters the nucleotide sugar metabolism through a reaction with GTP producing a GDP-mannose and releasing a pyrophosphate, all through a mannose-1-phosphate guanylyltransferase. GDP-mannose is then dehydrated to produce GDP-4-dehydro-6-deoxy-alpha-D-mannose through a GDP-mannose 4,6-dehydratase. This compound is then used to synthesize GDP-Beta-L-fucose through a NADPH dependent GDP-L-fucose synthase.
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.PW000887MetabolicAmino 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.PW000895Metabolicgalactose degradation/Leloir PathwayThe degradation of galactose, also known as Leloir pathway, requires 3 main enzymes once Beta-D-galactose has been converted to galactose through an Aldose-1-epimerase. These are: galactokinase , galactose-1-phosphate uridylyltransferase and UDP-glucose 4-epimerase. Beta-D-galactose can be uptaken from the environment through a galactose proton symporter. It can also be produced by lactose degradation involving a lactose permease to uptake lactose from the environment and a beta-galactosidase to turn lactose into Beta-D-galactose.
Galactose is degraded through the following process:
Beta-D-galactose is introduced into the cytoplasm through a galactose proton symporter, or it can be synthesized from an alpha lactose that is introduced into the cytoplasm through a lactose permease. Alpha lactose interacts with water through a beta-galactosidase resulting in a beta-D-glucose and beta-D-galactose. Beta-D-galactose is isomerized into D-galactose. D-Galactose undergoes phosphorylation through a galactokinase, hence producing galactose 1 phosphate. On the other side of the pathway, a gluose-1-phosphate (product of the interaction of alpha-D-glucose 6-phosphate with a phosphoglucomutase resulting in a alpha-D-glucose-1-phosphate, an isomer of Glucose 1-phosphate, or an isomer of Beta-D-glucose 1-phosphate) interacts with UTP and a hydrogen ion in order to produce a uridine diphosphate glucose. This is followed by the interaction of galactose-1-phosphate with an established amount of uridine diphosphate glucose through a galactose-1-phosphate uridylyltransferase, which in turn output a glucose-1-phosphate and a uridine diphosphate galactose. The glucose -1-phosphate is transformed into a uridine diphosphate glucose through UTP--glucose-1-phosphate uridylyltransferase. The product, uridine diphosphate glucose, can undergo a reversible reaction in which it can be turned into uridine diphosphategalactose through an UDP-glucose 4-epimerase, and so the cycle can keep going as long as more lactose or galactose is imported into the cell.
PW000884Metabolictrehalose biosynthesis IUnder conditions of elevated osmotic strength, E. coli can regulate the osmotic strength of the cytoplasm by accumulating K+ ions and some organic molecules, commonly called osmoprotectants or compatible solutes. The preferred osmoprotectant of E. coli is glycine betaine. However, its synthesis relies on an external supply of proline, betaines, or choline. When these compounds are not available, a cell can achieve a moderate level of osmotic tolerance by accumulation of glutamate and trehalose.
E. coli synthesizes and accumulates trehalose when exposed to osmotic stress and low temperatures. It is synthesized from UDP-glucose and glucose-6-phosphate via trehalose-6-phosphate, by the action of two enzymes, trehalose-6-phosphate synthase and trehalose-6-phosphate phosphatase. Expression of both genes encoding the two enzymes, otsA and otsB, is osmotically regulated. Transcription from these genes increases during osmotic stress and cold shock and when the cells enter stationary phase, and requires the stress sigma factor RpoS. Synthesis of trehalose is also stimulated directly by K+ ion-dependent activation of trehalose-6-phosphate synthase enzyme.
Under osmotic stress, E. coli overproduces trehalose, some of which is excreted to the periplasmic space. Once there, it is degraded by the periplasmic trehalase. This process was named "a futile cycle for controlling the cytoplasmic level of trehalose". (EcoCyc)PW002088MetabolicGDP-mannose biosynthesisPWY-5659D-mannose degradationMANNCAT-PWY2-<I>O</I>-α-mannosyl-D-glycerate degradationPWY0-1300Specdb::NmrOneD335838Specdb::NmrOneD335839Specdb::NmrOneD335840Specdb::NmrOneD335841Specdb::NmrOneD335842Specdb::NmrOneD335843Specdb::NmrOneD335844Specdb::NmrOneD335845Specdb::NmrOneD335846Specdb::NmrOneD335847Specdb::NmrOneD335848Specdb::NmrOneD335849Specdb::NmrOneD335850Specdb::NmrOneD335851Specdb::NmrOneD335852Specdb::NmrOneD335853Specdb::NmrOneD335854Specdb::NmrOneD335855Specdb::NmrOneD335856Specdb::NmrOneD335857Specdb::MsMs23591Specdb::MsMs23592Specdb::MsMs23593Specdb::MsMs30389Specdb::MsMs30390Specdb::MsMs30391HMDB0107865127388338C0027517369MANNOSE-6PM6DMannose 6-phosphateKeseler, 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-D114.22080510van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." 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Am J Med Genet A. 2005 Sep 1;137(3):235-40.16094673Beljaars L, Molema G, Weert B, Bonnema H, Olinga P, Groothuis GM, Meijer DK, Poelstra K: Albumin modified with mannose 6-phosphate: A potential carrier for selective delivery of antifibrotic drugs to rat and human hepatic stellate cells. Hepatology. 1999 May;29(5):1486-93.10216133van der Ploeg AT, van der Kraaij AM, Willemsen R, Kroos MA, Loonen MC, Koster JF, Reuser AJ: Rat heart perfusion as model system for enzyme replacement therapy in glycogenosis type II. Pediatr Res. 1990 Oct;28(4):344-7.2235132Yatziv S, Barfi G, Newburg DS: Lysosomal hydrolases in blood-derived macrophages of patients with I-cell disease. J Lab Clin Med. 1986 Oct;108(4):365-8.3093618Puolakkainen M, Kuo CC, Campbell LA: Chlamydia pneumoniae uses the mannose 6-phosphate/insulin-like growth factor 2 receptor for infection of endothelial cells. 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Folia Microbiologica (Prague, Czech Republic) (1981), 26(2), 103-6.http://hmdb.ca/system/metabolites/msds/000/000/969/original/HMDB01078.pdf?1358462788Mannose-6-phosphate isomeraseP00946MANA_ECOLImanAhttp://ecmdb.ca/proteins/P00946.xmlPhosphoenolpyruvate-protein phosphotransferaseP08839PT1_ECOLIptsIhttp://ecmdb.ca/proteins/P08839.xmlPhosphomannomutaseP24175MANB_ECOLImanBhttp://ecmdb.ca/proteins/P24175.xmlAlpha,alpha-trehalose-phosphate synthase [UDP-forming]P31677OTSA_ECOLIotsAhttp://ecmdb.ca/proteins/P31677.xmlGlucose-specific phosphotransferase enzyme IIA componentP69783PTGA_ECOLIcrrhttp://ecmdb.ca/proteins/P69783.xmlPTS system glucose-specific EIICB componentP69786PTGCB_ECOLIptsGhttp://ecmdb.ca/proteins/P69786.xmlPTS system mannose-specific EIIAB componentP69797PTNAB_ECOLImanXhttp://ecmdb.ca/proteins/P69797.xmlSugar phosphatase supHP75792SUPH_ECOLIsupHhttp://ecmdb.ca/proteins/P75792.xmlMannose permease IIC componentP69801PTNC_ECOLImanYhttp://ecmdb.ca/proteins/P69801.xmlMannose permease IID componentP69805PTND_ECOLImanZhttp://ecmdb.ca/proteins/P69805.xmlAlpha-mannosidase mngBP54746MNGB_ECOLImngBhttp://ecmdb.ca/proteins/P54746.xmlPhosphocarrier protein HPrP0AA04PTHP_ECOLIptsHhttp://ecmdb.ca/proteins/P0AA04.xmlPTS system glucose-specific EIICB componentP69786PTGCB_ECOLIptsGhttp://ecmdb.ca/proteins/P69786.xmlMannose permease IIC componentP69801PTNC_ECOLImanYhttp://ecmdb.ca/proteins/P69801.xmlMannose permease IID componentP69805PTND_ECOLImanZhttp://ecmdb.ca/proteins/P69805.xmlOuter membrane protein NP77747OMPN_ECOLIompNhttp://ecmdb.ca/proteins/P77747.xmlOuter membrane pore protein EP02932PHOE_ECOLIphoEhttp://ecmdb.ca/proteins/P02932.xmlHexose phosphate transport proteinP0AGC0UHPT_ECOLIuhpThttp://ecmdb.ca/proteins/P0AGC0.xmlOuter membrane protein FP02931OMPF_ECOLIompFhttp://ecmdb.ca/proteins/P02931.xmlOuter membrane protein CP06996OMPC_ECOLIompChttp://ecmdb.ca/proteins/P06996.xmlPhosphoenolpyruvic acid + D-Mannose > Mannose 6-phosphate + Pyruvic acidTRANS-RXN-165Water + 2(alpha-D-Mannosyl-6-phosphate)-D-glycerate > Glyceric acid + Mannose 6-phosphateRXN0-5216Water + Mannose 6-phosphate > D-Mannose + PhosphateMannose 6-phosphate <> Fructose 6-phosphateMANNPISOM-RXND-Mannose 1-phosphate <> Mannose 6-phosphateR01818PHOSMANMUT-RXNMannose 6-phosphate <> D-Mannose 1-phosphateR01818Mannose 6-phosphate <> beta-D-Fructose 6-phosphateR01819Protein N(pi)-phospho-L-histidine + D-Mannose <> Protein histidine + Mannose 6-phosphateR02630D-Mannose + Adenosine triphosphate > Hydrogen ion + Mannose 6-phosphate + ADPMANNKIN-RXND-Mannose + Phosphoenolpyruvic acid > Mannose 6-phosphate + Pyruvic acidTRANS-RXN-165Mannose 6-phosphate > Fructose 6-phosphateAlpha-D-mannose 1-phosphate > Mannose 6-phosphate2-O-(6-Phospho-alpha-D-mannosyl)-D-glycerate + Water > Mannose 6-phosphate + Glyceric acid2(alpha-D-Mannosyl-6-phosphate)-D-glycerate + Water <> Mannose 6-phosphate + Glyceric acidR09645 α-D-glucose 6-phosphate + Mannose 6-phosphate > α-D-glucose 1-phosphatePW_R003348α-D-glucose 6-phosphate + Mannose 6-phosphate > Alpha-D-glucose 1-phosphatePW_R003556alpha-D-Glucose + HPr - phosphorylated > α-D-glucose 6-phosphate + HPr + Mannose 6-phosphatePW_RCT000133UDP-Glucose + Mannose 6-phosphate > alpha,alpha-Trehalose 6-phosphate + Uridine 5'-diphosphate + Hydrogen ionPW_R006093