2.0 2012-05-31 10:22:49 -0600 2015-09-13 12:56:06 -0600 ECMDB00169 M2MDB000070 D-Mannose D-Mannose is a carbohydrate. High-mannose-type oligosaccharides have been shown to play important roles in protein quality control. Several intracellular proteins, such as lectins, chaperones and glycan-processing enzymes, are involved in this process. These include calnexin/calreticulin, UDP-glucose:glycoprotein glucosyltransferase (UGGT), cargo receptors (such as VIP36 and ERGIC-53), mannosidase-like proteins (e.g. EDEM and Htm1p) and ubiquitin ligase (Fbs). They are thought to recognize high-mannose-type glycans with subtly different structures. Mannose-binding lectin (MBL) is an important constituent of the innate immune system. This protein binds through multiple lectin domains to the repeating sugar arrays that decorate many microbial surfaces, and is then able to activate the complement system through a specific protease called MBL-associated protease-2. The primary pathway for the formation of L-fucose in procaryotic and eucaryotic cells is from D-mannose via an internal oxidation reduction and then epimerization of GDP-D-mannose to produce GDP-L-fucose. (PMID: 9488699, 16154739, 11414367) (+)-mannose (+-)-mannose Carubinose Carubinose (van) D(+)-Mannose D-Mannopyranose D-Mannose DL-mannose Hexose Mannopyranose Mannopyranoside Mannose Mannose (van) Nchembio828-comp8 Seminose C6H12O6 180.1559 180.063388116 (3S,4S,5S,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol β-glucose 3458-28-4 OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O InChI=1S/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3-,4+,5+,6?/m1/s1 WQZGKKKJIJFFOK-QTVWNMPRSA-N Solid Cytosol Extra-organism Periplasm logp -2.57 ALOGPS logs 0.64 ALOGPS solubility 7.82e+02 g/l ALOGPS melting_point 132 oC logp -2.9 ChemAxon pka_strongest_acidic 11.3 ChemAxon pka_strongest_basic -3 ChemAxon iupac (3S,4S,5S,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol ChemAxon average_mass 180.1559 ChemAxon mono_mass 180.063388116 ChemAxon smiles OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O ChemAxon formula C6H12O6 ChemAxon inchi InChI=1S/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3-,4+,5+,6?/m1/s1 ChemAxon inchikey WQZGKKKJIJFFOK-QTVWNMPRSA-N ChemAxon polar_surface_area 110.38 ChemAxon refractivity 35.92 ChemAxon polarizability 16.14 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 6 ChemAxon donor_count 5 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 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 Specdb::CMs 405 Specdb::CMs 406 Specdb::CMs 407 Specdb::CMs 408 Specdb::CMs 409 Specdb::CMs 1578 Specdb::CMs 1597 Specdb::CMs 2635 Specdb::CMs 30346 Specdb::CMs 30347 Specdb::CMs 30348 Specdb::CMs 30778 Specdb::CMs 30779 Specdb::CMs 31047 Specdb::CMs 31048 Specdb::CMs 37335 Specdb::NmrOneD 1134 Specdb::NmrOneD 1187 Specdb::NmrOneD 4169 Specdb::MsMs 269 Specdb::MsMs 270 Specdb::MsMs 178584 Specdb::MsMs 178585 Specdb::MsMs 178586 Specdb::MsMs 180903 Specdb::MsMs 180904 Specdb::MsMs 180905 Specdb::MsMs 447486 Specdb::NmrTwoD 1184 HMDB00169 18950 17893 C00159 16024 MANNOSE D-Mannose Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. 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Journal of the American Chemical Society (1947), 69 1963-5. http://hmdb.ca/system/metabolites/msds/000/000/119/original/HMDB00169.pdf?1358894047 Alpha-galactosidase P06720 AGAL_ECOLI melA http://ecmdb.ca/proteins/P06720.xml Phosphoenolpyruvate-protein phosphotransferase P08839 PT1_ECOLI ptsI http://ecmdb.ca/proteins/P08839.xml GDP-mannose mannosyl hydrolase P32056 NUDD_ECOLI nudD http://ecmdb.ca/proteins/P32056.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 Phosphocarrier protein HPr P0AA04 PTHP_ECOLI ptsH http://ecmdb.ca/proteins/P0AA04.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 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 + Mannose 6-phosphate > D-Mannose + Phosphate Guanosine diphosphate mannose + Water > Guanosine diphosphate + Hydrogen ion + D-Mannose GDPMANMANHYDRO-RXN Epimelibiose + Water <> D-Mannose + D-Galactose R01329 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 <> D-fructose MANNOSE-ISOMERASE-RXN D-Mannose + Phosphoenolpyruvic acid > Mannose 6-phosphate + Pyruvic acid TRANS-RXN-165 Guanosine diphosphate mannose + Water > Guanosine diphosphate + D-Mannose