2.0 2015-09-08 17:50:04 -0600 2015-09-14 16:46:33 -0600 ECMDB24208 M2MDB006325 D-allopyranose D-allopyranose is an intermediate in D-allose degradation pathway in E.coli. It is a substrate for the enzyme D-allose kinase which catalyzes the reaction D-allopyranose + ATP → aldehydo-D-allose 6-phosphate + ADP + H+ BioCyc compound: D-Allopyranose). C6H12O6 180.1559 180.063388116 OCC1OC(O)C(O)C(O)C1O InChI=1S/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2 WQZGKKKJIJFFOK-UHFFFAOYSA-N logp -2.41 ALOGPS logs -0.04 ALOGPS solubility 3.39e+02 g/l ALOGPS average_mass 180.1559 ChemAxon mono_mass 180.063388116 ChemAxon smiles OCC1OC(O)C(O)C(O)C1O ChemAxon formula C6H12O6 ChemAxon inchi InChI=1S/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2 ChemAxon inchikey WQZGKKKJIJFFOK-UHFFFAOYSA-N ChemAxon formal_charge 0 ChemAxon 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 D-allulose degradation E. coli can utilize D-allose as the sole source of carbon for growth. D-allose is transported into the cell in unphosphorylated form via the D-allose ABC transporter. AlsK, the D-allose kinase which phosphorylates D-allose, is not essential for this pathway. Allose-6-phosphate isomerase and allulose-6-phosphate 3-epimerase catalyze the remaining reactions resulting in D-allulose 6 phosphate and Beta-D-fructofuranose 6-phosphate respectively. Once Beta D fructofuranose 6-phosphate is synthesized, it goes into the glycolysis and pyruvatedehydrogenase pathway. PW000825 Metabolic Mannose Metabolism D-mannose can serve as a total source of carbon and energy for growth of E. coli. Alpha-D-mannose is introduced into the cytoplasm through a mannose PTS permease. Because mannose is taken up via a phosphotransferase system (PTS), the first intracellular species is D-mannose-6-phosphate. mannose-6-phosphate isomerase converts D-mannose-6-phosphate to D-fructose-6-phosphate, an intermediate of glycolysis, and hence it flows through the pathways of central metabolism to satisfy the cell's need for precursor metabolites, reducing power, and metabolic energy. The first two enzymes in the pathway (SEE VERTICAL SECTION) catalyze isomerizations that interconvert phosphorylated aldohexoses (β-D-glucose-6-phosphate, D-mannose-6-phosphate) and phosphorylated ketohexoses (D-fructose-6-phosphate). The reaction catalyzed by mannose-6-phosphate isomerase that produces D-mannose-6-phosphate is the first committed step in the biosynthesis of the activated mannose donor GDP-α-D-mannose. D-mannose-6-phosphate is then converted to GDP-D-mannose by the interaction of phosphomannomutase and mannose-1-phosphate guanylyltransferase . As for the bottom part L-fucose is biosynthesized as the sugar nucleotide GDP-L-fucose. Its biosynthesis from GDP-D-mannose begins with dehydration of this compound to GDP-4-dehydro-6-deoxy-D-mannose by the product of gene gmd. Then the bifunctional GDP-fucose synthase catalyzes the two-step (epimerase/reductase) synthesis of GDP-fucose from GDP-4-dehydro-6-deoxy-D-mannose via a GDP-4-dehydro-6-L-deoxygalactose intermediate. L-fucose is then incorporated into the colanic acid building blocks biosynthesis pathway. PW000822 Metabolic colanic acid building blocks biosynthesis The colonic acid building blocks biosynthesis starts with a Beta-D-Glucose undergoing a transport reaction mediated by a glucose PTS permease. The permease phosphorylates the Beta-D-Glucose, producing a Beta-D-Glucose 6-phosphate. This compound can either change to an Alpha-D-Glucose 6-phosphate spontaneously or into a fructose 6-phosphate through a glucose-6-phosphate isomerase. The latter compound can also be present in E.coli through the interaction of D-fructose and a mannose PTS permease which phosphorylate the D-fructose. Fructose 6-phosphate interacts in a reversible reaction with mannose-6-phosphate isomerase in order to produce a Alpha-D-mannose 6-phosphate. This compound can also be present in E.coli through the interaction of Alpha-D-mannose and a mannose PTS permease which phosphorylates the alpha-D-mannose. Alpha-D-mannose 6-phosphate interacts in a reversible reaction with a phosphomannomutase to produce a alpha-D-mannose 1-phosphate. This compound in turn with a hydrogen ion and gtp undergoes a reaction with a mannose-1-phosphate guanylyltransferase, releasing a pyrophosphate and producing a guanosine diphosphate mannose. Guanosine diphosphate mannose interacts with gdp-mannose 4,6-dehydratase releasing a water, and gdp-4-dehydro-6-deoxy-D-mannose. This compound in turn with hydrogen ion and NADPH interact with GDP-L-fucose synthase releasing NADP and producing a GDP-L-fucose. The Alpha-D-Glucose 6-phosphate interacts in a reversible reaction with phosphoglucomutase-1 to produce a alpha-D-glucose 1-phosphate. This in turn with UTP and hydrogen ion interact with UTP--glucose-1-phosphate uridyleltransferase releasing a pyrophosphate and UDP-glucose. UDP-glucose can either interact with galactose-1-phosphate uridylyltransferase to produce a UDP-galactose or in turn with NAD and water interact with UDP-glucose 6-dehydrogenase releasing a NADH and a hydrogen ion and producing a UDP-glucuronate. GDP-L-fucose, UDP-glucose, UDP-galactose and UDP-glucuronate are sugars that need to be activated in the form of nucleotide sugar prior to their assembly into colanic acid, also known as M antigen. Colanic acid is an extracellular polysaccharide which has been linked to a cluster of 19 genes(wca). PW000951 Metabolic Specdb::CMs 72540 Specdb::EiMs 1995 Specdb::NmrOneD 1961 Specdb::NmrOneD 21622 Specdb::NmrOneD 21623 Specdb::NmrOneD 21624 Specdb::NmrOneD 21625 Specdb::NmrOneD 21626 Specdb::NmrOneD 21627 Specdb::NmrOneD 21628 Specdb::NmrOneD 21629 Specdb::NmrOneD 21630 Specdb::NmrOneD 21631 Specdb::NmrOneD 21632 Specdb::NmrOneD 21633 Specdb::NmrOneD 21634 Specdb::NmrOneD 21635 Specdb::NmrOneD 21636 Specdb::NmrOneD 21637 Specdb::NmrOneD 21638 Specdb::NmrOneD 21639 Specdb::NmrOneD 21640 Specdb::NmrOneD 21641 Specdb::MsMs 2280 Specdb::MsMs 2281 Specdb::MsMs 2282 Specdb::MsMs 1218415 Specdb::MsMs 1218416 Specdb::MsMs 1218417 Specdb::MsMs 2781547 Specdb::MsMs 2781548 Specdb::MsMs 2781549 Specdb::MsMs 2926936 Specdb::MsMs 2926937 Specdb::MsMs 2926938 Specdb::NmrTwoD 1895 D-allose kinase P32718 ALSK_ECOLI alsK http://ecmdb.ca/proteins/P32718.xml D-allose import ATP-binding protein AlsA P32721 ALSA_ECOLI alsA http://ecmdb.ca/proteins/P32721.xml PTS system mannose-specific EIIAB component P69797 PTNAB_ECOLI manX http://ecmdb.ca/proteins/P69797.xml D-allose transport system permease protein AlsC P32720 ALSC_ECOLI alsC http://ecmdb.ca/proteins/P32720.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 D-allose-binding periplasmic protein P39265 ALSB_ECOLI alsB http://ecmdb.ca/proteins/P39265.xml D-allose import ATP-binding protein AlsA P32721 ALSA_ECOLI alsA http://ecmdb.ca/proteins/P32721.xml D-allose transport system permease protein AlsC P32720 ALSC_ECOLI alsC http://ecmdb.ca/proteins/P32720.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 D-allose-binding periplasmic protein P39265 ALSB_ECOLI alsB http://ecmdb.ca/proteins/P39265.xml D-allopyranose + Adenosine triphosphate > Adenosine diphosphate + Hydrogen ion + aldehydo-D-allose 6-phosphate + ADP + aldehydo-D-allose 6-phosphate PW_R002964 D-allopyranose + HPr - phosphorylated > α-D-mannose 6-phosphate + HPr PW_RCT000114 D-allopyranose + Adenosine triphosphate + Water > D-allopyranose + Adenosine diphosphate + Hydrogen ion + Phosphate + ADP PW_RCT000115 D-allopyranose + Adenosine triphosphate + Water > D-allopyranose + Adenosine diphosphate + Hydrogen ion + Phosphate + ADP PW_RCT000115