2.02012-05-31 14:25:31 -06002015-06-03 17:19:14 -0600ECMDB20063M2MDB0009122(alpha-D-Mannosyl)-D-glycerate2(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(α-D-mannosyl)-D-glycerate2(α-D-mannosyl)-D-glyceric acid2(a-D-Mannosyl)-D-glycerate2(a-D-Mannosyl)-D-glyceric acid2(alpha-D-Mannosyl)-D-glycerate2(alpha-D-Mannosyl)-D-glyceric acid2(α-D-Mannosyl)-D-glycerate2(α-D-Mannosyl)-D-glyceric acid2-(α-D-mannopyranosyl)-D-glycerate2-(α-D-mannopyranosyl)-D-glyceric acid2-(a-D-Mannopyranosyl)-D-glycerate2-(a-D-Mannopyranosyl)-D-glyceric acid2-(alpha-D-Mannopyranosyl)-D-glycerate2-(alpha-D-Mannopyranosyl)-D-glyceric acid2-(α-D-Mannopyranosyl)-D-glycerate2-(α-D-Mannopyranosyl)-D-glyceric acid2-O-a-Mannosyl-D-glycerate2-O-a-Mannosyl-D-glyceric acid2-O-alpha-Mannosyl-D-glycerate2-O-alpha-Mannosyl-D-glyceric acid2-O-α-Mannosyl-D-glycerate2-O-α-Mannosyl-D-glyceric acida-Mannosylglyceratea-Mannosylglyceric acidAlpha-MannosylglycerateAlpha-Mannosylglyceric acidMannosylglycerateMannosylglyceric acidα-Mannosylglycerateα-Mannosylglyceric acidC9H16O9268.2179268.07943211(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)=OInChI=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/s1DDXCFDOPXBPUJC-SAYMMRJXSA-NExtra-organismPeriplasmlogp-2.87logs0.06solubility3.05e+02 g/llogp-3.3pka_strongest_acidic3.35pka_strongest_basic-3iupac(2R)-3-hydroxy-2-{[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propanoic acidaverage_mass268.2179mono_mass268.07943211smiles[H][C@](CO)(O[C@@]1([H])O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O)[C@]1([H])O)C(O)=OformulaC9H16O9inchiInChI=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/s1inchikeyDDXCFDOPXBPUJC-SAYMMRJXSA-Npolar_surface_area156.91refractivity52.8polarizability23.81rotatable_bond_count5acceptor_count9donor_count6physiological_charge-1formal_charge0Fructose and mannose metabolismec00051Phosphotransferase system (PTS)ec02060Collection of Reactions without pathwaysPW001891Metabolicinner membrane transportlist 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 addedPW000786Metabolic2-O-alpha-mannosyl-D-glycerate degradation2-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)PW002096MetabolicSpecdb::CMs1083616Specdb::NmrOneD252828Specdb::NmrOneD252829Specdb::NmrOneD252830Specdb::NmrOneD252831Specdb::NmrOneD252832Specdb::NmrOneD252833Specdb::NmrOneD252834Specdb::NmrOneD252835Specdb::NmrOneD252836Specdb::NmrOneD252837Specdb::NmrOneD252838Specdb::NmrOneD252839Specdb::NmrOneD252840Specdb::NmrOneD252841Specdb::NmrOneD252842Specdb::NmrOneD252843Specdb::NmrOneD252844Specdb::NmrOneD252845Specdb::NmrOneD252846Specdb::NmrOneD252847Specdb::MsMs26054Specdb::MsMs26055Specdb::MsMs26056Specdb::MsMs32612Specdb::MsMs32613Specdb::MsMs326144432624573823C11544158472-O-ALPHA-MANNOSYL-D-GLYCERATEKeseler, 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-D590.21097882Kanehisa, 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-D114.22080510Empadinhas, 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 186:4075-4084.15205409Empadinhas, 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 79:76-93.21166895Sa-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 64:760-763.18678952Phosphoenolpyruvate-protein phosphotransferaseP08839PT1_ECOLIptsIhttp://ecmdb.ca/proteins/P08839.xmlHeat-responsive suppressor hrsAP54745HRSA_ECOLIhrsAhttp://ecmdb.ca/proteins/P54745.xmlPutative mannosyl-3-phosphoglycerate phosphataseP76329MPGP_ECOLIyedPhttp://ecmdb.ca/proteins/P76329.xmlPhosphocarrier protein HPrP0AA04PTHP_ECOLIptsHhttp://ecmdb.ca/proteins/P0AA04.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.xmlMannosyl-D-glycerate transport/metabolism system repressor MngRP13669MNGR_ECOLImngRhttp://ecmdb.ca/proteins/P13669.xmlPhosphoenolpyruvic acid + 2(alpha-D-Mannosyl)-D-glycerate > 2(alpha-D-Mannosyl-6-phosphate)-D-glycerate + Pyruvic acidRXN0-25222-(alpha-D-Mannosyl)-3-phosphoglycerate + Water + 2(alpha-D-mannosyl)-3-phosphoglycerate <> 2(alpha-D-Mannosyl)-D-glycerate + PhosphateR05790Phosphoenolpyruvic acid + 2(alpha-D-Mannosyl)-D-glycerate > 2(alpha-D-Mannosyl-6-phosphate)-D-glycerate + Pyruvic acidRXN0-25222(alpha-D-mannosyl)-3-phosphoglycerate + Water > 2(alpha-D-Mannosyl)-D-glycerate + Inorganic phosphate2(alpha-D-Mannosyl)-D-glycerate + HPr - phosphorylated > 2(alpha-D-Mannosyl-6-phosphate)-D-glycerate + HPrPW_RCT0001772-(alpha-D-Mannosyl)-3-phosphoglycerate + Water > 2(alpha-D-Mannosyl)-D-glycerate + PhosphatePW_R0058052(alpha-D-Mannosyl)-D-glycerate + HPr - phosphorylated > 2-O-(6-Phospho-alpha-D-mannosyl)-D-glycerate + HPrPW_RCT000192