2.0 2012-05-31 13:44:41 -0600 2015-10-15 16:13:50 -0600 ECMDB01078 M2MDB000244 Mannose 6-phosphate Mannose-6-phosphate (M6P) is a molecule bound by lectin. M6P is converted to fructose 6-phosphate by mannose phosphate isomerase. (Wikipedia) &alpha;-D-mannose-6-P &alpha;-D-mannose-6-phosphate &alpha;-D-mannose-6-phosphoric acid a-D-Mannose-6-P a-D-Mannose-6-phosphate a-D-Mannose-6-phosphoric acid a-delta-Mannose-6-P a-delta-Mannose-6-phosphate a-delta-Mannose-6-phosphoric acid a-δ-Mannose-6-P a-δ-Mannose-6-phosphate a-δ-Mannose-6-phosphoric acid Alpha-D-Mannose-6-P Alpha-D-Mannose-6-phosphate alpha-D-Mannose-6-phosphoric acid Alpha-delta-Mannose-6-P Alpha-delta-Mannose-6-phosphate alpha-delta-Mannose-6-phosphoric acid D-Mannose 6-phosphate D-Mannose 6-phosphoric acid Delta-Mannose 6-phosphate delta-Mannose 6-phosphoric acid Man-6-p Man6P Mannose 6-phosphate Mannose 6-phosphoric acid Mannose-6-phosphate Mannose-6-phosphoric acid α-D-Mannose-6-P α-D-Mannose-6-phosphate α-D-Mannose-6-phosphoric acid α-δ-Mannose-6-P α-δ-Mannose-6-phosphate α-δ-Mannose-6-phosphoric acid δ-Mannose 6-phosphate δ-Mannose 6-phosphoric acid C6H13O9P 260.1358 260.029718526 (3,4,5,6-tetrahydroxyoxan-2-yl)methyl phosphate (3,4,5,6-tetrahydroxyoxan-2-yl)methyl phosphate 3672-15-9 O[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@@H]1O InChI=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/s1 NBSCHQHZLSJFNQ-RWOPYEJCSA-N Solid Cytosol Extra-organism Periplasm logp -2.30 ALOGPS logs -0.49 ALOGPS solubility 9.50e+01 g/l ALOGPS logp -3.1 ChemAxon pka_strongest_acidic 1.22 ChemAxon pka_strongest_basic -3.6 ChemAxon iupac (3,4,5,6-tetrahydroxyoxan-2-yl)methyl phosphate ChemAxon average_mass 260.1358 ChemAxon mono_mass 260.029718526 ChemAxon smiles O[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@@H]1O ChemAxon formula C6H13O9P ChemAxon inchi InChI=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/s1 ChemAxon inchikey NBSCHQHZLSJFNQ-RWOPYEJCSA-N ChemAxon polar_surface_area 162.57 ChemAxon refractivity 44.55 ChemAxon polarizability 20.49 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 8 ChemAxon donor_count 4 ChemAxon physiological_charge -2 ChemAxon formal_charge -2 ChemAxon Fructose and mannose metabolism ec00051 Galactose metabolism Galactose 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 PW000821 ec00052 Metabolic Amino sugar and nucleotide sugar metabolism ec00520 Phosphotransferase system (PTS) ec02060 Metabolic pathways eco01100 Amino sugar and nucleotide sugar metabolism II The 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. PW000887 Metabolic Amino sugar and nucleotide sugar metabolism III The 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. PW000895 Metabolic galactose degradation/Leloir Pathway The 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. PW000884 Metabolic trehalose biosynthesis I Under 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) PW002088 Metabolic GDP-mannose biosynthesis PWY-5659 D-mannose degradation MANNCAT-PWY 2-<I>O</I>-&alpha;-mannosyl-D-glycerate degradation PWY0-1300 Specdb::NmrOneD 335838 Specdb::NmrOneD 335839 Specdb::NmrOneD 335840 Specdb::NmrOneD 335841 Specdb::NmrOneD 335842 Specdb::NmrOneD 335843 Specdb::NmrOneD 335844 Specdb::NmrOneD 335845 Specdb::NmrOneD 335846 Specdb::NmrOneD 335847 Specdb::NmrOneD 335848 Specdb::NmrOneD 335849 Specdb::NmrOneD 335850 Specdb::NmrOneD 335851 Specdb::NmrOneD 335852 Specdb::NmrOneD 335853 Specdb::NmrOneD 335854 Specdb::NmrOneD 335855 Specdb::NmrOneD 335856 Specdb::NmrOneD 335857 Specdb::MsMs 23591 Specdb::MsMs 23592 Specdb::MsMs 23593 Specdb::MsMs 30389 Specdb::MsMs 30390 Specdb::MsMs 30391 HMDB01078 65127 388338 C00275 17369 MANNOSE-6P M6D Mannose 6-phosphate Keseler, I. 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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?1358462788 Mannose-6-phosphate isomerase P00946 MANA_ECOLI manA http://ecmdb.ca/proteins/P00946.xml Phosphoenolpyruvate-protein phosphotransferase P08839 PT1_ECOLI ptsI http://ecmdb.ca/proteins/P08839.xml Phosphomannomutase P24175 MANB_ECOLI manB http://ecmdb.ca/proteins/P24175.xml Alpha,alpha-trehalose-phosphate synthase [UDP-forming] P31677 OTSA_ECOLI otsA http://ecmdb.ca/proteins/P31677.xml Glucose-specific phosphotransferase enzyme IIA component P69783 PTGA_ECOLI crr http://ecmdb.ca/proteins/P69783.xml PTS system glucose-specific EIICB component P69786 PTGCB_ECOLI ptsG http://ecmdb.ca/proteins/P69786.xml PTS system mannose-specific EIIAB component P69797 PTNAB_ECOLI manX http://ecmdb.ca/proteins/P69797.xml Sugar phosphatase supH P75792 SUPH_ECOLI supH http://ecmdb.ca/proteins/P75792.xml Mannose permease IIC component P69801 PTNC_ECOLI manY http://ecmdb.ca/proteins/P69801.xml Mannose permease IID component P69805 PTND_ECOLI manZ http://ecmdb.ca/proteins/P69805.xml Alpha-mannosidase mngB P54746 MNGB_ECOLI mngB http://ecmdb.ca/proteins/P54746.xml Phosphocarrier protein HPr P0AA04 PTHP_ECOLI ptsH http://ecmdb.ca/proteins/P0AA04.xml PTS system glucose-specific EIICB component P69786 PTGCB_ECOLI ptsG http://ecmdb.ca/proteins/P69786.xml Mannose permease IIC component P69801 PTNC_ECOLI manY http://ecmdb.ca/proteins/P69801.xml Mannose permease IID component P69805 PTND_ECOLI manZ http://ecmdb.ca/proteins/P69805.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 Hexose phosphate transport protein P0AGC0 UHPT_ECOLI uhpT http://ecmdb.ca/proteins/P0AGC0.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 Phosphoenolpyruvic acid + D-Mannose > Mannose 6-phosphate + Pyruvic acid TRANS-RXN-165 Water + 2(alpha-D-Mannosyl-6-phosphate)-D-glycerate > Glyceric acid + Mannose 6-phosphate RXN0-5216 Water + Mannose 6-phosphate > D-Mannose + Phosphate Mannose 6-phosphate <> Fructose 6-phosphate MANNPISOM-RXN D-Mannose 1-phosphate <> Mannose 6-phosphate R01818 PHOSMANMUT-RXN Mannose 6-phosphate <> D-Mannose 1-phosphate R01818 Mannose 6-phosphate <> beta-D-Fructose 6-phosphate R01819 Protein N(pi)-phospho-L-histidine + D-Mannose <> Protein histidine + Mannose 6-phosphate R02630 D-Mannose + Adenosine triphosphate > Hydrogen ion + Mannose 6-phosphate + ADP MANNKIN-RXN D-Mannose + Phosphoenolpyruvic acid > Mannose 6-phosphate + Pyruvic acid TRANS-RXN-165 Mannose 6-phosphate > Fructose 6-phosphate Alpha-D-mannose 1-phosphate > Mannose 6-phosphate 2-O-(6-Phospho-alpha-D-mannosyl)-D-glycerate + Water > Mannose 6-phosphate + Glyceric acid 2(alpha-D-Mannosyl-6-phosphate)-D-glycerate + Water <> Mannose 6-phosphate + Glyceric acid R09645 α-D-glucose 6-phosphate + Mannose 6-phosphate > α-D-glucose 1-phosphate PW_R003348 α-D-glucose 6-phosphate + Mannose 6-phosphate > Alpha-D-glucose 1-phosphate PW_R003556 alpha-D-Glucose + HPr - phosphorylated > α-D-glucose 6-phosphate + HPr + Mannose 6-phosphate PW_RCT000133 UDP-Glucose + Mannose 6-phosphate > alpha,alpha-Trehalose 6-phosphate + Uridine 5'-diphosphate + Hydrogen ion PW_R006093