2.0 2012-05-31 14:25:31 -0600 2015-06-03 17:19:14 -0600 ECMDB20063 M2MDB000912 2(alpha-D-Mannosyl)-D-glycerate 2(alpha-D-mannosyl)-D-glycerate is a member of the chemical class known as Hexoses. These are monosaccharides in which the sugar unit is a hexose. Mannosylglycerate (MG) is a common compatible solute found in thermophilic and hyperthermophilic prokaryotes. (PMID 15205409) Rubrobacter xylanophilus is the only Gram-positive bacterium known to synthesize the compatible solute mannosylglycerate (MG), which is commonly found in hyperthermophilic archaea and some thermophilic bacteria. (PMID 18678952) Rubrobacter xylanophilus is the only actinobacterium known to accumulate the organic solute mannosylglycerate (MG); moreover, the accumulation of MG is constitutive. (PMID 21166895) 2(&alpha;-D-mannosyl)-D-glycerate 2(&alpha;-D-mannosyl)-D-glyceric acid 2(a-D-Mannosyl)-D-glycerate 2(a-D-Mannosyl)-D-glyceric acid 2(alpha-D-Mannosyl)-D-glycerate 2(alpha-D-Mannosyl)-D-glyceric acid 2(α-D-Mannosyl)-D-glycerate 2(α-D-Mannosyl)-D-glyceric acid 2-(&alpha;-D-mannopyranosyl)-D-glycerate 2-(&alpha;-D-mannopyranosyl)-D-glyceric acid 2-(a-D-Mannopyranosyl)-D-glycerate 2-(a-D-Mannopyranosyl)-D-glyceric acid 2-(alpha-D-Mannopyranosyl)-D-glycerate 2-(alpha-D-Mannopyranosyl)-D-glyceric acid 2-(α-D-Mannopyranosyl)-D-glycerate 2-(α-D-Mannopyranosyl)-D-glyceric acid 2-O-a-Mannosyl-D-glycerate 2-O-a-Mannosyl-D-glyceric acid 2-O-alpha-Mannosyl-D-glycerate 2-O-alpha-Mannosyl-D-glyceric acid 2-O-α-Mannosyl-D-glycerate 2-O-α-Mannosyl-D-glyceric acid a-Mannosylglycerate a-Mannosylglyceric acid Alpha-Mannosylglycerate Alpha-Mannosylglyceric acid Mannosylglycerate Mannosylglyceric acid α-Mannosylglycerate α-Mannosylglyceric acid C9H16O9 268.2179 268.07943211 (2R)-3-hydroxy-2-{[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propanoic acid (2R)-3-hydroxy-2-{[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propanoic acid [H][C@](CO)(O[C@@]1([H])O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O)[C@]1([H])O)C(O)=O InChI=1S/C9H16O9/c10-1-3-5(12)6(13)7(14)9(17-3)18-4(2-11)8(15)16/h3-7,9-14H,1-2H2,(H,15,16)/t3-,4-,5-,6+,7+,9-/m1/s1 DDXCFDOPXBPUJC-SAYMMRJXSA-N Extra-organism Periplasm logp -2.87 ALOGPS logs 0.06 ALOGPS solubility 3.05e+02 g/l ALOGPS logp -3.3 ChemAxon pka_strongest_acidic 3.35 ChemAxon pka_strongest_basic -3 ChemAxon iupac (2R)-3-hydroxy-2-{[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propanoic acid ChemAxon average_mass 268.2179 ChemAxon mono_mass 268.07943211 ChemAxon smiles [H][C@](CO)(O[C@@]1([H])O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O)[C@]1([H])O)C(O)=O ChemAxon formula C9H16O9 ChemAxon inchi InChI=1S/C9H16O9/c10-1-3-5(12)6(13)7(14)9(17-3)18-4(2-11)8(15)16/h3-7,9-14H,1-2H2,(H,15,16)/t3-,4-,5-,6+,7+,9-/m1/s1 ChemAxon inchikey DDXCFDOPXBPUJC-SAYMMRJXSA-N ChemAxon polar_surface_area 156.91 ChemAxon refractivity 52.8 ChemAxon polarizability 23.81 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 9 ChemAxon donor_count 6 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Fructose and mannose metabolism ec00051 Phosphotransferase system (PTS) ec02060 Collection of Reactions without pathways PW001891 Metabolic inner membrane transport list 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 added PW000786 Metabolic 2-O-alpha-mannosyl-D-glycerate degradation 2-O-α-Mannosyl-D-glycerate (MG) is an osmolyte utilized by hyperthermophilic archaea and bacteria. E. coli is able to utilize MG as a carbon source but not as protection against osmotic stress. MG utilization is controlled by the divergently transcribed mngR gene and mngAB operon. MngR acts as a repressor of the expression both mngR and mngAB. MngA is the EII of a PEP-dependent sugar phosphotransferase system responsible for the uptake and phosphorylation of MG to 2-O-(6-phospho-α-mannosyl)-D-glycerate, which is subsequently converted to mannose-6-phosphate and glycerate by the α-mannosidase MngB. Glycerate can be converted to 2-phosphoglycerate by glycerate kinase I encoded by the garK gene which is also induced when cells are grown in MG. (EcoCyc) PW002096 Metabolic Specdb::CMs 1083616 Specdb::NmrOneD 252828 Specdb::NmrOneD 252829 Specdb::NmrOneD 252830 Specdb::NmrOneD 252831 Specdb::NmrOneD 252832 Specdb::NmrOneD 252833 Specdb::NmrOneD 252834 Specdb::NmrOneD 252835 Specdb::NmrOneD 252836 Specdb::NmrOneD 252837 Specdb::NmrOneD 252838 Specdb::NmrOneD 252839 Specdb::NmrOneD 252840 Specdb::NmrOneD 252841 Specdb::NmrOneD 252842 Specdb::NmrOneD 252843 Specdb::NmrOneD 252844 Specdb::NmrOneD 252845 Specdb::NmrOneD 252846 Specdb::NmrOneD 252847 Specdb::MsMs 26054 Specdb::MsMs 26055 Specdb::MsMs 26056 Specdb::MsMs 32612 Specdb::MsMs 32613 Specdb::MsMs 32614 443262 4573823 C11544 15847 2-O-ALPHA-MANNOSYL-D-GLYCERATE 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 Kanehisa, 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. 22080510 Empadinhas, N., Albuquerque, L., Costa, J., Zinder, S. H., Santos, M. A., Santos, H., da Costa, M. S. (2004). "A gene from the mesophilic bacterium Dehalococcoides ethenogenes encodes a novel mannosylglycerate synthase." J Bacteriol 186:4075-4084. 15205409 Empadinhas, N., Pereira, P. J., Albuquerque, L., Costa, J., Sa-Moura, B., Marques, A. T., Macedo-Ribeiro, S., da Costa, M. S. (2011). "Functional and structural characterization of a novel mannosyl-3-phosphoglycerate synthase from Rubrobacter xylanophilus reveals its dual substrate specificity." Mol Microbiol 79:76-93. 21166895 Sa-Moura, B., Albuquerque, L., Empadinhas, N., da Costa, M. S., Pereira, P. J., Macedo-Ribeiro, S. (2008). "Crystallization and preliminary crystallographic analysis of mannosyl-3-phosphoglycerate synthase from Rubrobacter xylanophilus." Acta Crystallogr Sect F Struct Biol Cryst Commun 64:760-763. 18678952 Phosphoenolpyruvate-protein phosphotransferase P08839 PT1_ECOLI ptsI http://ecmdb.ca/proteins/P08839.xml Heat-responsive suppressor hrsA P54745 HRSA_ECOLI hrsA http://ecmdb.ca/proteins/P54745.xml Putative mannosyl-3-phosphoglycerate phosphatase P76329 MPGP_ECOLI yedP http://ecmdb.ca/proteins/P76329.xml Phosphocarrier protein HPr P0AA04 PTHP_ECOLI ptsH http://ecmdb.ca/proteins/P0AA04.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 Mannosyl-D-glycerate transport/metabolism system repressor MngR P13669 MNGR_ECOLI mngR http://ecmdb.ca/proteins/P13669.xml Phosphoenolpyruvic acid + 2(alpha-D-Mannosyl)-D-glycerate > 2(alpha-D-Mannosyl-6-phosphate)-D-glycerate + Pyruvic acid RXN0-2522 2-(alpha-D-Mannosyl)-3-phosphoglycerate + Water + 2(alpha-D-mannosyl)-3-phosphoglycerate <> 2(alpha-D-Mannosyl)-D-glycerate + Phosphate R05790 Phosphoenolpyruvic acid + 2(alpha-D-Mannosyl)-D-glycerate > 2(alpha-D-Mannosyl-6-phosphate)-D-glycerate + Pyruvic acid RXN0-2522 2(alpha-D-mannosyl)-3-phosphoglycerate + Water > 2(alpha-D-Mannosyl)-D-glycerate + Inorganic phosphate 2(alpha-D-Mannosyl)-D-glycerate + HPr - phosphorylated > 2(alpha-D-Mannosyl-6-phosphate)-D-glycerate + HPr PW_RCT000177 2-(alpha-D-Mannosyl)-3-phosphoglycerate + Water > 2(alpha-D-Mannosyl)-D-glycerate + Phosphate PW_R005805 2(alpha-D-Mannosyl)-D-glycerate + HPr - phosphorylated > 2-O-(6-Phospho-alpha-D-mannosyl)-D-glycerate + HPr PW_RCT000192