2.02012-05-31 09:56:02 -06002015-09-13 12:56:05 -0600ECMDB00048M2MDB000015MelibioseMelibiose is a disaccharide consisting of one galactose and one glucose moiety in an alpha (1-6) glycosidic linkage. This sugar is produced and metabolized only by enteric and lactic acid bacteria and other microbes. Melibiose can be broken down by gut microflora such as E. coli. Melibiose is first imported by the melibiose permease, MelB, and then converted to alpha-D-glucose and alpha-D-galactose by the galactosidase encoded by melA. (HMDB) In fact, E. coli K-12 is able to utilize melibiose as a sole source of carbon. (PMID 786627)α-D-Galp-(1->6)-D-Glc6-(α-D-galactosido)-D-glucose6-(a-D-Galactosido)-D-glucose6-(a-delta-Galactosido)-delta-glucose6-(a-δ-galactosido)-δ-Glucose6-(alpha-D-Galactosido)-D-glucose6-(D-Galactosido)-D-glucose6-(D-Galactosido)-delta-glucose6-(D-galactosido)-δ-Glucose6-(α-D-galactosido)-D-Glucose6-O-α-D-Galactopyranosyl-D-glucose6-O-(α-D-galactopyranosyl)-D-glucopyranose6-O-(a-D-Galactopyranosyl)-D-glucopyranose6-O-(alpha-D-Galactopyranosyl)-D-glucopyranose6-O-(α-D-Galactopyranosyl)-D-glucopyranose6-O-a-D-Galactopyranosyl-D-Glucose6-O-a-delta-Galactopyranosyl-delta-glucose6-O-a-δ-Galactopyranosyl-δ-glucose6-O-alpha-D-Galactopyranosyl-D-Glucose6-O-alpha-delta-Galactopyranosyl-delta-Glucose6-O-Hexopyranosylhexose6-O-α-D-Galactopyranosyl-D-glucose6-O-α-δ-Galactopyranosyl-δ-glucosea-D-Galp-(1->6)-D-GLCa-D-Melibiosea-delta-Melibiosea-Melibiosea-δ-MelibioseAlpha-D-Galp-(1->6)-D-GlcAlpha-D-MelibioseAlpha-delta-MelibioseAlpha-MelibioseD-(+)-MelibioseD-Gal-α(1->6)-D-glucoseD-Gal-a(1->6)-D-glucoseD-Gal-alpha(1->6)-D-glucoseD-Gal-α(1->6)-D-glucoseD-MelibioseD-MellibioseDelta-(+)-MelibioseDelta-MelibioseMelibioseMellibioseα-D-Galp-(1->6)-D-GLCα-D-Melibioseα-Melibioseα-δ-Melibioseδ-(+)-Melibioseδ-MelibioseC12H22O11342.2965342.116211546(2S,3R,4S,5R,6R)-6-({[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxane-2,3,4,5-tetrolepimelibiose585-99-9OC[C@H]1O[C@H](OC[C@H]2OC(O)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@H]1OInChI=1S/C12H22O11/c13-1-3-5(14)8(17)10(19)12(23-3)21-2-4-6(15)7(16)9(18)11(20)22-4/h3-20H,1-2H2/t3-,4-,5+,6-,7+,8+,9-,10-,11?,12+/m1/s1DLRVVLDZNNYCBX-ABXHMFFYSA-NSolidCytosolExtra-organismPeriplasmlogp-3.00ALOGPSlogs0.17ALOGPSsolubility5.11e+02 g/lALOGPSmelting_point84 oClogp-4.7ChemAxonpka_strongest_acidic11.25ChemAxonpka_strongest_basic-3ChemAxoniupac(2S,3R,4S,5R,6R)-6-({[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxane-2,3,4,5-tetrolChemAxonaverage_mass342.2965ChemAxonmono_mass342.116211546ChemAxonsmilesOC[C@H]1O[C@H](OC[C@H]2OC(O)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@H]1OChemAxonformulaC12H22O11ChemAxoninchiInChI=1S/C12H22O11/c13-1-3-5(14)8(17)10(19)12(23-3)21-2-4-6(15)7(16)9(18)11(20)22-4/h3-20H,1-2H2/t3-,4-,5+,6-,7+,8+,9-,10-,11?,12+/m1/s1ChemAxoninchikeyDLRVVLDZNNYCBX-ABXHMFFYSA-NChemAxonpolar_surface_area189.53ChemAxonrefractivity68.34ChemAxonpolarizability30.85ChemAxonrotatable_bond_count4ChemAxonacceptor_count11ChemAxondonor_count8ChemAxonphysiological_charge0ChemAxonformal_charge0ChemAxonGalactose 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
PW000821ec00052Metabolicinner membrane transportlist of inner membrane transport complexes, transporting compounds from the periplasmic space to the cytosol
This pathway should be updated regularly with the new inner membrae transports addedPW000786Metabolicmelibiose degradationPWY0-1301Specdb::CMs16790Specdb::CMs39089Specdb::CMs102701Specdb::CMs102702Specdb::CMs102703Specdb::CMs102704Specdb::CMs102705Specdb::CMs102706Specdb::CMs102707Specdb::CMs102708Specdb::CMs102709Specdb::CMs102710Specdb::CMs102711Specdb::CMs102712Specdb::CMs102713Specdb::CMs102714Specdb::NmrOneD5190Specdb::NmrOneD5191Specdb::MsMs303085Specdb::MsMs303086Specdb::MsMs303087Specdb::MsMs345958Specdb::MsMs345959Specdb::MsMs345960Specdb::MsMs1218236Specdb::MsMs1218237Specdb::MsMs1218238Specdb::NmrTwoD2028HMDB00048440658389538C0540228053MELIBIOSEKeseler, 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." Anal Biochem 370:17-25.17765195Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948.18331064Schmid, K., Schmitt, R. (1976). "Raffinose metabolism in Escherichia coli K12. Purification and properties of a new alpha-galactosidase specified by a transmissible plasmid." Eur J Biochem 67:95-104.786627Almeida IC, Milani SR, Gorin PA, Travassos LR: Complement-mediated lysis of Trypanosoma cruzi trypomastigotes by human anti-alpha-galactosyl antibodies. J Immunol. 1991 Apr 1;146(7):2394-400.1706399Sharma A, Ahmed H, Allen HJ: Isolation of a melibiose-binding protein from human spleen. Glycoconj J. 1995 Feb;12(1):17-21.7795409Steuer MK, Steuer M, Bonkowsky V, Gabius HJ, Hofstadter F: Characterization of sugar receptor expression by neoglycoproteins in oral and oropharyngeal squamous cell carcinomas. Eur Arch Otorhinolaryngol. 1995;252(5):292-7.7576587Vaughan HA, Loveland BE, Sandrin MS: Gal alpha(1,3)Gal is the major xenoepitope expressed on pig endothelial cells recognized by naturally occurring cytotoxic human antibodies. Transplantation. 1994 Oct 27;58(8):879-82.7524207Barboza Junior MS, Silva TM, Guerrant RL, Lima AA: Measurement of intestinal permeability using mannitol and lactulose in children with diarrheal diseases. Braz J Med Biol Res. 1999 Dec;32(12):1499-504.10585631Furukawa K, Ying R, Nakajima T, Matsuki T: Hemagglutinins in fungus extracts and their blood group specificity. Exp Clin Immunogenet. 1995;12(4):223-31.8919354Gibbons RJ, Qureshi JV: Inhibition of adsorption of Streptococcus mutans strains to saliva-treated hydroxyapatite by galactose and certain amines. Infect Immun. 1979 Dec;26(3):1214-7.528053Nicolopoulou A, Zoumbou K, Papageorgacopoulou N, Papapetropoulou M: Metabolic and compositional changes in Escherichia coli cells starved in seawater. Microbiol Res. 1994 Nov;149(4):343-50.7842233Wu AM, Song SC, Chen YY, Gilboa-Garber N: Defining the carbohydrate specificities of aplysia gonad lectin exhibiting a peculiar D-galacturonic acid affinity. J Biol Chem. 2000 May 12;275(19):14017-24.10799474Rietra PJ, Van den Bergh FA, Tager JM: Properties of the residual alpha-galactosidase activity in the tissues of a Fabry hemizygote. Clin Chim Acta. 1975 Aug 4;62(3):401-13.809216Colby SM, Harrington DJ, Russell RR: Identification and genetic characterisation of melibiose-negative isolates of Streptococcus mutans. Caries Res. 1995;29(5):407-12.8521444Tomita K, Nagura T, Okuhara Y, Nakajima-Adachi H, Shigematsu N, Aritsuka T, Kaminogawa S, Hachimura S: Dietary melibiose regulates th cell response and enhances the induction of oral tolerance. Biosci Biotechnol Biochem. 2007 Nov;71(11):2774-80. Epub 2007 Nov 7.17986780Pictet, Ame; Vogel, Hans. The synthesis of melibiose. Helvetica Chimica Acta (1927), 10 280.http://hmdb.ca/system/metabolites/msds/000/000/033/original/HMDB00048.pdf?1358462799Alpha-galactosidaseP06720AGAL_ECOLImelAhttp://ecmdb.ca/proteins/P06720.xmlMelibiose carrier proteinP02921MELB_ECOLImelBhttp://ecmdb.ca/proteins/P02921.xmlSugar efflux transporter CP31436SETC_ECOLIsetChttp://ecmdb.ca/proteins/P31436.xmlSugar efflux transporterP31122SOTB_ECOLIsotBhttp://ecmdb.ca/proteins/P31122.xmlOuter membrane protein NP77747OMPN_ECOLIompNhttp://ecmdb.ca/proteins/P77747.xmlOuter membrane pore protein EP02932PHOE_ECOLIphoEhttp://ecmdb.ca/proteins/P02932.xmlOuter membrane protein FP02931OMPF_ECOLIompFhttp://ecmdb.ca/proteins/P02931.xmlOuter membrane protein CP06996OMPC_ECOLIompChttp://ecmdb.ca/proteins/P06996.xmlWater + Melibiose > D-Galactose + D-GlucoseR01101Melibiose + Water <> D-Galactose + D-GlucoseR01101D-Gal alpha 1->6D-Gal alpha 1->6D-Glucose + Water <> D-Galactose + MelibioseR05549Water + Melibiose > D-Galactose + b-D-GlucoseALPHAGALACTOSID-RXNMelibiose + Water > Alpha-D-Galactose + Beta-D-Glucose + b-D-GlucosePW_R003298