2.02012-05-31 10:22:49 -06002015-09-13 12:56:06 -0600ECMDB00169M2MDB000070D-MannoseD-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(+-)-mannoseCarubinoseCarubinose (van)D(+)-MannoseD-MannopyranoseD-MannoseDL-mannoseHexoseMannopyranoseMannopyranosideMannoseMannose (van)Nchembio828-comp8SeminoseC6H12O6180.1559180.063388116(3S,4S,5S,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrolβ-glucose3458-28-4OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1OInChI=1S/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3-,4+,5+,6?/m1/s1WQZGKKKJIJFFOK-QTVWNMPRSA-NSolidCytosolExtra-organismPeriplasmlogp-2.57logs0.64solubility7.82e+02 g/lmelting_point132 oClogp-2.9pka_strongest_acidic11.3pka_strongest_basic-3iupac(3S,4S,5S,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrolaverage_mass180.1559mono_mass180.063388116smilesOC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1OformulaC6H12O6inchiInChI=1S/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3-,4+,5+,6?/m1/s1inchikeyWQZGKKKJIJFFOK-QTVWNMPRSA-Npolar_surface_area110.38refractivity35.92polarizability16.14rotatable_bond_count1acceptor_count6donor_count5physiological_charge0formal_charge0Fructose 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)ec02060Specdb::CMs405Specdb::CMs406Specdb::CMs407Specdb::CMs408Specdb::CMs409Specdb::CMs1578Specdb::CMs1597Specdb::CMs2635Specdb::CMs30346Specdb::CMs30347Specdb::CMs30348Specdb::CMs30778Specdb::CMs30779Specdb::CMs31047Specdb::CMs31048Specdb::CMs37335Specdb::NmrOneD1134Specdb::NmrOneD1187Specdb::NmrOneD4169Specdb::MsMs269Specdb::MsMs270Specdb::MsMs178584Specdb::MsMs178585Specdb::MsMs178586Specdb::MsMs180903Specdb::MsMs180904Specdb::MsMs180905Specdb::MsMs447486Specdb::NmrTwoD1184HMDB001691895017893C0015916024MANNOSED-MannoseKanehisa, 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 80:2939-2948.18331064Park, S. H., Pastuszak, I., Drake, R., Elbein, A. D. (1998). "Purification to apparent homogeneity and properties of pig kidney L-fucose kinase." J Biol Chem 273:5685-5691.9488699Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4.19212411Shoemaker JD, Elliott WH: Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. J Chromatogr. 1991 Jan 2;562(1-2):125-38.2026685Alton G, Hasilik M, Niehues R, Panneerselvam K, Etchison JR, Fana F, Freeze HH: Direct utilization of mannose for mammalian glycoprotein biosynthesis. Glycobiology. 1998 Mar;8(3):285-95.9451038Wu X, Rush JS, Karaoglu D, Krasnewich D, Lubinsky MS, Waechter CJ, Gilmore R, Freeze HH: Deficiency of UDP-GlcNAc:Dolichol Phosphate N-Acetylglucosamine-1 Phosphate Transferase (DPAGT1) causes a novel congenital disorder of Glycosylation Type Ij. Hum Mutat. 2003 Aug;22(2):144-50.12872255Thio CL, Mosbruger T, Astemborski J, Greer S, Kirk GD, O'Brien SJ, Thomas DL: Mannose binding lectin genotypes influence recovery from hepatitis B virus infection. J Virol. 2005 Jul;79(14):9192-6.15994813Lee SH, Nam SY, Chung BC: Altered profile of endogenous steroids in the urine of patients with prolactinoma. Clin Biochem. 1998 Oct;31(7):529-35.9812172Nakagawa F, Schulte BA, Spicer SS: Lectin cytochemical evaluation of somatosensory neurons and their peripheral and central processes in rat and man. Cell Tissue Res. 1986;245(3):579-89.3757018Otter M, Zockova P, Kuiper J, van Berkel TJ, Barrett-Bergshoeff MM, Rijken DC: Isolation and characterization of the mannose receptor from human liver potentially involved in the plasma clearance of tissue-type plasminogen activator. Hepatology. 1992 Jul;16(1):54-9.1618483Hu P, Parenti G, Keulemans J, Hoogeveen AT: Lysosomal tartrate sensitive acid phosphatase deficiency in cells which contain lysosomal "high uptake forms". Biochem Biophys Res Commun. 1990 Mar 16;167(2):520-7.2322240Hermentin P, Witzel R, Kanzy EJ, Diderrich G, Hoffmann D, Metzner H, Vorlop J, Haupt H: The hypothetical N-glycan charge: a number that characterizes protein glycosylation. Glycobiology. 1996 Mar;6(2):217-30.8727793DeRossi C, Bode L, Eklund EA, Zhang F, Davis JA, Westphal V, Wang L, Borowsky AD, Freeze HH: Ablation of mouse phosphomannose isomerase (Mpi) causes mannose 6-phosphate accumulation, toxicity, and embryonic lethality. J Biol Chem. 2006 Mar 3;281(9):5916-27. Epub 2005 Dec 8.16339137Miras MT, Aunis D, Mandel P: Studies on the interaction of dopamine beta-hydroxylase from various sources with phytohaemagglutinins. Clin Chim Acta. 1975 Nov 3;64(3):293-302.1183043Van der Ploeg AT, Kroos MA, Willemsen R, Brons NH, Reuser AJ: Intravenous administration of phosphorylated acid alpha-glucosidase leads to uptake of enzyme in heart and skeletal muscle of mice. J Clin Invest. 1991 Feb;87(2):513-8.1991835Cavallone D, Malagolini N, Monti A, Wu XR, Serafini-Cessi F: Variation of high mannose chains of Tamm-Horsfall glycoprotein confers differential binding to type 1-fimbriated Escherichia coli. J Biol Chem. 2004 Jan 2;279(1):216-22. Epub 2003 Oct 21.14570881Adlerberth I, Ahrne S, Johansson ML, Molin G, Hanson LA, Wold AE: A mannose-specific adherence mechanism in Lactobacillus plantarum conferring binding to the human colonic cell line HT-29. Appl Environ Microbiol. 1996 Jul;62(7):2244-51.8779562Hung CS, Bouckaert J, Hung D, Pinkner J, Widberg C, DeFusco A, Auguste CG, Strouse R, Langermann S, Waksman G, Hultgren SJ: Structural basis of tropism of Escherichia coli to the bladder during urinary tract infection. Mol Microbiol. 2002 May;44(4):903-15.12010488Condaminet B, Peguet-Navarro J, Stahl PD, Dalbiez-Gauthier C, Schmitt D, Berthier-Vergnes O: Human epidermal Langerhans cells express the mannose-fucose binding receptor. Eur J Immunol. 1998 Nov;28(11):3541-51.9842897Go S, Sato C, Furuhata K, Kitajima K: Oral ingestion of mannose alters the expression level of deaminoneuraminic acid (KDN) in mouse organs. Glycoconj J. 2006 Jul;23(5-6):411-21.16897182Burk MR, Troeger C, Brinkhaus R, Holzgreve W, Hahn S: Severely reduced presence of tissue macrophages in the basal plate of pre-eclamptic placentae. Placenta. 2001 Apr;22(4):309-16.11286566Sarkar K, Das PK: Protective effect of neoglycoprotein-conjugated muramyl dipeptide against Leishmania donovani infection: the role of cytokines. J Immunol. 1997 Jun 1;158(11):5357-65.9164956Kusmierz J, DeGeorge JJ, Sweeney D, May C, Rapoport SI: Quantitative analysis of polyols in human plasma and cerebrospinal fluid. J Chromatogr. 1989 Dec 29;497:39-48.2625478Biessen EA, Noorman F, van Teijlingen ME, Kuiper J, Barrett-Bergshoeff M, Bijsterbosch MK, Rijken DC, van Berkel TJ: Lysine-based cluster mannosides that inhibit ligand binding to the human mannose receptor at nanomolar concentration. J Biol Chem. 1996 Nov 8;271(45):28024-30.8910412Smith ME: Phagocytic properties of microglia in vitro: implications for a role in multiple sclerosis and EAE. Microsc Res Tech. 2001 Jul 15;54(2):81-94.11455615Della Porta M, Danova M, Rigolin GM, Brugnatelli S, Rovati B, Tronconi C, Fraulini C, Russo Rossi A, Riccardi A, Castoldi G: Dendritic cells and vascular endothelial growth factor in colorectal cancer: correlations with clinicobiological findings. Oncology. 2005;68(2-3):276-84. Epub 2005 Jul 7.16015045Patnaik SK, Stanley P: Mouse large can modify complex N- and mucin O-glycans on alpha-dystroglycan to induce laminin binding. J Biol Chem. 2005 May 27;280(21):20851-9. Epub 2005 Mar 23.15788414Brysk MM, Miller J: Concanavalin A binding glycoprotein in human stratum corneum. J Invest Dermatol. 1984 Mar;82(3):280-2.6421939Takahashi I, Takahashi T, Mikami T, Komatsu M, Ohura T, Schuchman EH, Takada G: Acid sphingomyelinase: relation of 93lysine residue on the ratio of intracellular to secreted enzyme activity. Tohoku J Exp Med. 2005 Aug;206(4):333-40.15997205Akazawa S, Metzger BE, Freinkel N: Relationships between glucose and mannose during late gestation in normal pregnancy and pregnancy complicated by diabetes mellitus: concurrent concentrations in maternal plasma and amniotic fluid. J Clin Endocrinol Metab. 1986 May;62(5):984-9.3958133Blach-Olszewska Z: Innate immunity: cells, receptors, and signaling pathways. Arch Immunol Ther Exp (Warsz). 2005 May-Jun;53(3):245-53.15995585Pietila EM, Tuusa JT, Apaja PM, Aatsinki JT, Hakalahti AE, Rajaniemi HJ, Petaja-Repo UE: Inefficient maturation of the rat luteinizing hormone receptor. A putative way to regulate receptor numbers at the cell surface. J Biol Chem. 2005 Jul 15;280(28):26622-9. Epub 2005 May 18.15901736Carchon HA, Jaeken J: Determination of D-mannose in serum by capillary electrophoresis. Clin Chem. 2001;47(7):1319-21.11427470Ito Y, Hagihara S, Matsuo I, Totani K: Structural approaches to the study of oligosaccharides in glycoprotein quality control. Curr Opin Struct Biol. 2005 Oct;15(5):481-9.16154739Jack DL, Klein NJ, Turner MW: Mannose-binding lectin: targeting the microbial world for complement attack and opsonophagocytosis. Immunol Rev. 2001 Apr;180:86-99.11414367 Sowden, John C.; Fischer, Hermann O. L. Condensation of nitromethane with D- and L-arabinose: preparation of L-glucose and L-mannose. Journal of the American Chemical Society (1947), 69 1963-5.http://hmdb.ca/system/metabolites/msds/000/000/119/original/HMDB00169.pdf?1358894047Alpha-galactosidaseP06720AGAL_ECOLImelAhttp://ecmdb.ca/proteins/P06720.xmlPhosphoenolpyruvate-protein phosphotransferaseP08839PT1_ECOLIptsIhttp://ecmdb.ca/proteins/P08839.xmlGDP-mannose mannosyl hydrolaseP32056NUDD_ECOLInudDhttp://ecmdb.ca/proteins/P32056.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.xmlPhosphocarrier protein HPrP0AA04PTHP_ECOLIptsHhttp://ecmdb.ca/proteins/P0AA04.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.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 + Mannose 6-phosphate > D-Mannose + PhosphateGuanosine diphosphate mannose + Water > Guanosine diphosphate + Hydrogen ion + D-MannoseGDPMANMANHYDRO-RXNEpimelibiose + Water <> D-Mannose + D-GalactoseR01329Protein N(pi)-phospho-L-histidine + D-Mannose <> Protein histidine + Mannose 6-phosphateR02630D-Mannose + Adenosine triphosphate > Hydrogen ion + Mannose 6-phosphate + ADPMANNKIN-RXND-Mannose <> D-fructoseMANNOSE-ISOMERASE-RXND-Mannose + Phosphoenolpyruvic acid > Mannose 6-phosphate + Pyruvic acidTRANS-RXN-165Guanosine diphosphate mannose + Water > Guanosine diphosphate + D-Mannose