2.0 2012-05-31 14:50:02 -0600 2015-06-03 17:20:12 -0600 ECMDB20547 M2MDB001353 Diacetylchitobiose-6-phosphate Diacetylchitobiose-6-phosphate is a member of the chemical class known as Dihexoses. These are disaccharides containing two hexose carbohydrates. Diacetylchitobiose-6-phosphate is invovled in Chitobiose transport. r 15;80(8):2939-48.) Chitobiose-6-phosphate Chitobiose-6-phosphoric acid Diacetylchitobiose-6-phosphoric acid C16H29N2O14P 504.3802 504.135640158 N-[(2R,3R,4R,5S,6R)-5-{[(2R,3R,4R,5S,6R)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-[(phosphonooxy)methyl]oxan-2-yl]oxy}-2,4-dihydroxy-6-(hydroxymethyl)oxan-3-yl]ethanimidic acid N-[(2R,3R,4R,5S,6R)-5-{[(2R,3R,4R,5S,6R)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-[(phosphonooxy)methyl]oxan-2-yl]oxy}-2,4-dihydroxy-6-(hydroxymethyl)oxan-3-yl]ethanimidic acid [H][C@@]1(O)O[C@]([H])(CO)[C@@]([H])(O[C@@]2([H])O[C@]([H])(COP(O)(O)=O)[C@@]([H])(O)[C@]([H])(O)[C@@]2([H])N=C(C)O)[C@]([H])(O)[C@@]1([H])N=C(C)O InChI=1S/C16H29N2O14P/c1-5(20)17-9-13(24)14(7(3-19)30-15(9)25)32-16-10(18-6(2)21)12(23)11(22)8(31-16)4-29-33(26,27)28/h7-16,19,22-25H,3-4H2,1-2H3,(H,17,20)(H,18,21)(H2,26,27,28)/t7-,8-,9-,10-,11-,12-,13-,14-,15-,16-/m1/s1 KYKNQNQCPWDNAK-MVGRPQHISA-N Cytosol logp -2.18 ALOGPS logs -1.15 ALOGPS solubility 3.56e+01 g/l ALOGPS logp -3.8 ChemAxon pka_strongest_acidic 1.22 ChemAxon pka_strongest_basic -3.6 ChemAxon iupac N-[(2R,3R,4R,5S,6R)-5-{[(2R,3R,4R,5S,6R)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-[(phosphonooxy)methyl]oxan-2-yl]oxy}-2,4-dihydroxy-6-(hydroxymethyl)oxan-3-yl]ethanimidic acid ChemAxon average_mass 504.3802 ChemAxon mono_mass 504.135640158 ChemAxon smiles [H][C@@]1(O)O[C@]([H])(CO)[C@@]([H])(O[C@@]2([H])O[C@]([H])(COP(O)(O)=O)[C@@]([H])(O)[C@]([H])(O)[C@@]2([H])N=C(C)O)[C@]([H])(O)[C@@]1([H])N=C(C)O ChemAxon formula C16H29N2O14P ChemAxon inchi InChI=1S/C16H29N2O14P/c1-5(20)17-9-13(24)14(7(3-19)30-15(9)25)32-16-10(18-6(2)21)12(23)11(22)8(31-16)4-29-33(26,27)28/h7-16,19,22-25H,3-4H2,1-2H3,(H,17,20)(H,18,21)(H2,26,27,28)/t7-,8-,9-,10-,11-,12-,13-,14-,15-,16-/m1/s1 ChemAxon inchikey KYKNQNQCPWDNAK-MVGRPQHISA-N ChemAxon polar_surface_area 260.78 ChemAxon refractivity 102.46 ChemAxon polarizability 44.51 ChemAxon rotatable_bond_count 8 ChemAxon acceptor_count 15 ChemAxon donor_count 9 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Chitobiose Degradation The β-glucoside N,N'-diacetylchitobiose is the major breakdown product of chitin, the second most abundant biopolymer after cellulose. E. coli is capable of using N,N'-diacetylchitobiose as the sole source of carbon. Chitobiose is imported and concurrently phosphorylated to N,N'-diacetylchitobiose 6'-phosphate by the chitobiose PTS transporter. Recent evidence suggests that this is followed by deacetylation of the unphosphorylated acetylglucosamine moiety at the reducing end of N,N'-diacetylchitobiose 6'-phosphate by chito-oligosaccharide mono-deacetylase. N-monoacetylchitobiose 6'-phosphate is subsequently hydrolyzed by the glycosyl hydrolase monoacetylchitobiose-6-phosphate hydrolase to D-glucosamine and N-acetyl-D-glucosamine 6-phosphate. N-acetyl-D-glucosamine 6-phosphate enters the N-acetylglucosamine degradation I pathway for conversion to β-D-fructofuranose 6-phosphate, which enters glycolysis. The fate of D-glucosamine is currently unclear; when used as a carbon source, D-glucosamine enters the cell via a PTS transporter and is thereby phosphorylated. It is possible that an intracellular D-glucosamine kinase activity enables utilization of this compound. (EcoCyc) PW002042 Metabolic chitobiose degradation PWY0-1309 Specdb::CMs 1083771 Specdb::NmrOneD 267368 Specdb::NmrOneD 267369 Specdb::NmrOneD 267370 Specdb::NmrOneD 267371 Specdb::NmrOneD 267372 Specdb::NmrOneD 267373 Specdb::NmrOneD 267374 Specdb::NmrOneD 267375 Specdb::NmrOneD 267376 Specdb::NmrOneD 267377 Specdb::NmrOneD 267378 Specdb::NmrOneD 267379 Specdb::NmrOneD 267380 Specdb::NmrOneD 267381 Specdb::NmrOneD 267382 Specdb::NmrOneD 267383 Specdb::NmrOneD 267384 Specdb::NmrOneD 267385 Specdb::NmrOneD 267386 Specdb::NmrOneD 267387 Specdb::MsMs 23567 Specdb::MsMs 23568 Specdb::MsMs 23569 Specdb::MsMs 30365 Specdb::MsMs 30366 Specdb::MsMs 30367 25200795 DIACETYLCHITOBIOSE-6-PHOSPHATE Keseler, 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. 21097882 Winder, 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. 18331064 PTS system mannitol-specific EIICBA component P00550 PTM3C_ECOLI mtlA http://ecmdb.ca/proteins/P00550.xml Phosphoenolpyruvate-protein phosphotransferase P08839 PT1_ECOLI ptsI http://ecmdb.ca/proteins/P08839.xml 6-phospho-beta-glucosidase P17411 CHBF_ECOLI chbF http://ecmdb.ca/proteins/P17411.xml Chitooligosaccharide deacetylase ChbG P37794 CHBG_ECOLI chbG http://ecmdb.ca/proteins/P37794.xml PTS system mannitol-specific EIICBA component P00550 PTM3C_ECOLI mtlA http://ecmdb.ca/proteins/P00550.xml Diacetylchitobiose-6-phosphate + Water > N-Acetyl-D-glucosamine + N-Acetyl-D-Glucosamine 6-Phosphate RXN0-5243 Phosphoenolpyruvic acid + Chitobiose > Diacetylchitobiose-6-phosphate + Pyruvic acid TRANS-RXN-155B Phosphoenolpyruvic acid + Chitobiose > Pyruvic acid + Diacetylchitobiose-6-phosphate TRANS-RXN-155B Diacetylchitobiose-6-phosphate + Water > N'-monoacetylchitobiose-6'-phosphate + Acetic acid PW_R005986 Diacetylchitobiose + HPr - phosphorylated > Diacetylchitobiose-6-phosphate + HPr PW_RCT000184