2.02012-05-31 13:01:37 -06002015-06-03 15:53:36 -0600ECMDB00853M2MDB000193N-Acetyl-b-D-galactosamineN-Acetyl-b-D-galactosamine is one of the eight essential sugars. It is important for cell communication. In galactose metabolism pathway, it is converted to N-Acetyl-b-D-galactosamine-6P by N-acetylgalactosamine-specific phosphotransferase enzyme B (EC 2.7.1.69).2-Deoxy-2-acetamido-b-D-galactopyranose2-Deoxy-2-acetamido-b-delta-galactopyranose2-Deoxy-2-acetamido-b-δ-galactopyranose2-Deoxy-2-acetamido-beta-D-galactopyranose2-Deoxy-2-acetamido-beta-delta-galactopyranose2-Deoxy-2-acetamido-β-D-galactopyranose2-Deoxy-2-acetamido-β-δ-galactopyranoseB-D-2-Acetamido-2-deoxy-Galactopyranoseb-delta-2-acetamido-2-Deoxy-galactopyranoseB-N-Acetyl-D-galactosamineb-N-Acetyl-delta-galactosamineb-N-Acetyl-δ-galactosamineB-N-Acetylgalactosamineb-δ-2-acetamido-2-Deoxy-galactopyranoseBeta-D-2-Acetamido-2-deoxy-GalactopyranoseBeta-delta-2-Acetamido-2-deoxy-GalactopyranoseBeta-N-Acetyl-D-galactosamineBeta-N-Acetyl-delta-galactosamineBeta-N-Acetylgalactosamineβ-D-2-acetamido-2-Deoxy-galactopyranoseβ-N-Acetyl-D-galactosamineβ-N-Acetyl-δ-galactosamineβ-N-Acetylgalactosamineβ-δ-2-acetamido-2-Deoxy-galactopyranoseC8H15NO6221.2078221.089937217N-[(2R,3R,4R,5R,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamideN-acetyl-β-D-galactosamine14131-60-3CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@H](O)[C@@H]1OInChI=1S/C8H15NO6/c1-3(11)9-5-7(13)6(12)4(2-10)15-8(5)14/h4-8,10,12-14H,2H2,1H3,(H,9,11)/t4-,5-,6+,7-,8-/m1/s1OVRNDRQMDRJTHS-JAJWTYFOSA-NSolidExtra-organismPeriplasmlogp-2.60logs0.06solubility2.54e+02 g/llogp-3.2pka_strongest_acidic11.6pka_strongest_basic-0.78iupacN-[(2R,3R,4R,5R,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamideaverage_mass221.2078mono_mass221.089937217smilesCC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@H](O)[C@@H]1OformulaC8H15NO6inchiInChI=1S/C8H15NO6/c1-3(11)9-5-7(13)6(12)4(2-10)15-8(5)14/h4-8,10,12-14H,2H2,1H3,(H,9,11)/t4-,5-,6+,7-,8-/m1/s1inchikeyOVRNDRQMDRJTHS-JAJWTYFOSA-Npolar_surface_area119.25refractivity47.02polarizability21.04rotatable_bond_count2acceptor_count6donor_count5physiological_charge0formal_charge0Galactose 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
PW000821ec00052MetabolicPhosphotransferase system (PTS)ec02060Specdb::CMs13451Specdb::CMs37804Specdb::CMs145838Specdb::CMs1080134Specdb::CMs1080135Specdb::CMs1080137Specdb::CMs1080139Specdb::CMs1080141Specdb::CMs1080143Specdb::CMs1080145Specdb::CMs1080147Specdb::CMs1080148Specdb::CMs1080150Specdb::CMs1080152Specdb::CMs1080154Specdb::CMs1080156Specdb::CMs1080158Specdb::CMs1080160Specdb::CMs1080162Specdb::CMs1080164Specdb::CMs1080166Specdb::CMs1080168Specdb::CMs1080170Specdb::CMs1080172Specdb::CMs1080173Specdb::NmrOneD7802Specdb::NmrOneD7803Specdb::NmrOneD7804Specdb::NmrOneD7805Specdb::NmrOneD7806Specdb::NmrOneD7807Specdb::NmrOneD7808Specdb::NmrOneD7809Specdb::NmrOneD7810Specdb::NmrOneD7811Specdb::NmrOneD7812Specdb::NmrOneD7813Specdb::NmrOneD7814Specdb::NmrOneD7815Specdb::NmrOneD7816Specdb::NmrOneD7817Specdb::NmrOneD7818Specdb::NmrOneD7819Specdb::NmrOneD7820Specdb::NmrOneD7821Specdb::MsMs23027Specdb::MsMs23028Specdb::MsMs23029Specdb::MsMs29825Specdb::MsMs29826Specdb::MsMs29827Specdb::MsMs3043759Specdb::MsMs3043760Specdb::MsMs3043761Specdb::MsMs3100048Specdb::MsMs3100049Specdb::MsMs3100050HMDB00853389452C05021NGAKanehisa, 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-D114.22080510Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30.12829005Barbas C, Garcia A, de Miguel L, Simo C: Evaluation of filter paper collection of urine samples for detection and measurement of organic acidurias by capillary electrophoresis. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Nov 15;780(1):73-82.12383482Garcia A, Barbas C, Aguilar R, Castro M: Capillary electrophoresis for rapid profiling of organic acidurias. Clin Chem. 1998 Sep;44(9):1905-11.9732975Gheri G, Bryk SG, Taddei G, Moncini D, Noci I: Sugar residues content and distribution in atrophic and hyperplastic postmenopausal human endometrium: lectin histochemistry. Histol Histopathol. 1996 Oct;11(4):861-7.8930627Sediva A, Stejskal J, Bartunkova J, Smetana K Jr, Gabius HJ: Detection of alpha(beta)-N-acetyl-D-galactosamine-binding sites in kidney--relation to Henoch-Schonlein-associated IgA nephropathy. Folia Biol (Praha). 1999;45(4):147-50.10732728Chaplin, David; Crout, David H. G.; Bornemann, Stephen; Hutchinson, David W.; Khan, Riaz. Conversion of 2-acetamido-2-deoxy-b-D-glucopyranose (N-acetylglucosamine) into 2-acetamido-2-deoxy-b-D-galactopyranose (N-acetylgalactosamine using a biotransformatN-acetylgalactosamine-specific phosphotransferase enzyme IIB component 2P42904PTPB2_ECOLIagaVhttp://ecmdb.ca/proteins/P42904.xmlBeta-hexosaminidaseP75949NAGZ_ECOLInagZhttp://ecmdb.ca/proteins/P75949.xmlN-acetylgalactosamine permease IIC component 1P42910PTPC1_ECOLIagaChttp://ecmdb.ca/proteins/P42910.xmlN-acetylgalactosamine permease IID componentP42911PTPD_ECOLIagaDhttp://ecmdb.ca/proteins/P42911.xmlPutative N-acetylgalactosamine permease IIC component 2P42905PTPC2_ECOLIagaWhttp://ecmdb.ca/proteins/P42905.xmlN-acetylgalactosamine permease IIC component 1P42910PTPC1_ECOLIagaChttp://ecmdb.ca/proteins/P42910.xmlN-acetylgalactosamine permease IID componentP42911PTPD_ECOLIagaDhttp://ecmdb.ca/proteins/P42911.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 + Globoside <> N-Acetyl-b-D-galactosamine + GlobotriaosylceramideR05963GM2 + Water <> GM3 + N-Acetyl-b-D-galactosamineR06004G13033 + Water <> G08421 + N-Acetyl-b-D-galactosamineR07809G06780 + Water <> G08421 + N-Acetyl-b-D-galactosamineR07810N-Acetyl-b-D-galactosamine + Protein N(pi)-phospho-L-histidine <> N-Acetyl-D-galactosamine 6-phosphate + Protein histidineR08366