2.0 2012-05-31 13:01:37 -0600 2015-06-03 15:53:36 -0600 ECMDB00853 M2MDB000193 N-Acetyl-b-D-galactosamine N-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-galactopyranose 2-Deoxy-2-acetamido-b-delta-galactopyranose 2-Deoxy-2-acetamido-b-δ-galactopyranose 2-Deoxy-2-acetamido-beta-D-galactopyranose 2-Deoxy-2-acetamido-beta-delta-galactopyranose 2-Deoxy-2-acetamido-β-D-galactopyranose 2-Deoxy-2-acetamido-β-δ-galactopyranose B-D-2-Acetamido-2-deoxy-Galactopyranose b-delta-2-acetamido-2-Deoxy-galactopyranose B-N-Acetyl-D-galactosamine b-N-Acetyl-delta-galactosamine b-N-Acetyl-δ-galactosamine B-N-Acetylgalactosamine b-δ-2-acetamido-2-Deoxy-galactopyranose Beta-D-2-Acetamido-2-deoxy-Galactopyranose Beta-delta-2-Acetamido-2-deoxy-Galactopyranose Beta-N-Acetyl-D-galactosamine Beta-N-Acetyl-delta-galactosamine Beta-N-Acetylgalactosamine β-D-2-acetamido-2-Deoxy-galactopyranose β-N-Acetyl-D-galactosamine β-N-Acetyl-δ-galactosamine β-N-Acetylgalactosamine β-δ-2-acetamido-2-Deoxy-galactopyranose C8H15NO6 221.2078 221.089937217 N-[(2R,3R,4R,5R,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide N-acetyl-β-D-galactosamine 14131-60-3 CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@H](O)[C@@H]1O InChI=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/s1 OVRNDRQMDRJTHS-JAJWTYFOSA-N Solid Extra-organism Periplasm logp -2.60 ALOGPS logs 0.06 ALOGPS solubility 2.54e+02 g/l ALOGPS logp -3.2 ChemAxon pka_strongest_acidic 11.6 ChemAxon pka_strongest_basic -0.78 ChemAxon iupac N-[(2R,3R,4R,5R,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide ChemAxon average_mass 221.2078 ChemAxon mono_mass 221.089937217 ChemAxon smiles CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@H](O)[C@@H]1O ChemAxon formula C8H15NO6 ChemAxon inchi InChI=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/s1 ChemAxon inchikey OVRNDRQMDRJTHS-JAJWTYFOSA-N ChemAxon polar_surface_area 119.25 ChemAxon refractivity 47.02 ChemAxon polarizability 21.04 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 6 ChemAxon donor_count 5 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon 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 Phosphotransferase system (PTS) ec02060 Specdb::CMs 13451 Specdb::CMs 37804 Specdb::CMs 145838 Specdb::CMs 1080134 Specdb::CMs 1080135 Specdb::CMs 1080137 Specdb::CMs 1080139 Specdb::CMs 1080141 Specdb::CMs 1080143 Specdb::CMs 1080145 Specdb::CMs 1080147 Specdb::CMs 1080148 Specdb::CMs 1080150 Specdb::CMs 1080152 Specdb::CMs 1080154 Specdb::CMs 1080156 Specdb::CMs 1080158 Specdb::CMs 1080160 Specdb::CMs 1080162 Specdb::CMs 1080164 Specdb::CMs 1080166 Specdb::CMs 1080168 Specdb::CMs 1080170 Specdb::CMs 1080172 Specdb::CMs 1080173 Specdb::NmrOneD 7802 Specdb::NmrOneD 7803 Specdb::NmrOneD 7804 Specdb::NmrOneD 7805 Specdb::NmrOneD 7806 Specdb::NmrOneD 7807 Specdb::NmrOneD 7808 Specdb::NmrOneD 7809 Specdb::NmrOneD 7810 Specdb::NmrOneD 7811 Specdb::NmrOneD 7812 Specdb::NmrOneD 7813 Specdb::NmrOneD 7814 Specdb::NmrOneD 7815 Specdb::NmrOneD 7816 Specdb::NmrOneD 7817 Specdb::NmrOneD 7818 Specdb::NmrOneD 7819 Specdb::NmrOneD 7820 Specdb::NmrOneD 7821 Specdb::MsMs 23027 Specdb::MsMs 23028 Specdb::MsMs 23029 Specdb::MsMs 29825 Specdb::MsMs 29826 Specdb::MsMs 29827 Specdb::MsMs 3043759 Specdb::MsMs 3043760 Specdb::MsMs 3043761 Specdb::MsMs 3100048 Specdb::MsMs 3100049 Specdb::MsMs 3100050 HMDB00853 389452 C05021 NGA Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. 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Histol Histopathol. 1996 Oct;11(4):861-7. 8930627 Sediva 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. 10732728 Chaplin, 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 biotransformat N-acetylgalactosamine-specific phosphotransferase enzyme IIB component 2 P42904 PTPB2_ECOLI agaV http://ecmdb.ca/proteins/P42904.xml Beta-hexosaminidase P75949 NAGZ_ECOLI nagZ http://ecmdb.ca/proteins/P75949.xml N-acetylgalactosamine permease IIC component 1 P42910 PTPC1_ECOLI agaC http://ecmdb.ca/proteins/P42910.xml N-acetylgalactosamine permease IID component P42911 PTPD_ECOLI agaD http://ecmdb.ca/proteins/P42911.xml Putative N-acetylgalactosamine permease IIC component 2 P42905 PTPC2_ECOLI agaW http://ecmdb.ca/proteins/P42905.xml N-acetylgalactosamine permease IIC component 1 P42910 PTPC1_ECOLI agaC http://ecmdb.ca/proteins/P42910.xml N-acetylgalactosamine permease IID component P42911 PTPD_ECOLI agaD http://ecmdb.ca/proteins/P42911.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 Water + Globoside <> N-Acetyl-b-D-galactosamine + Globotriaosylceramide R05963 GM2 + Water <> GM3 + N-Acetyl-b-D-galactosamine R06004 G13033 + Water <> G08421 + N-Acetyl-b-D-galactosamine R07809 G06780 + Water <> G08421 + N-Acetyl-b-D-galactosamine R07810 N-Acetyl-b-D-galactosamine + Protein N(pi)-phospho-L-histidine <> N-Acetyl-D-galactosamine 6-phosphate + Protein histidine R08366