2.0 2012-05-31 14:37:02 -0600 2015-06-03 17:19:42 -0600 ECMDB20281 M2MDB001121 Molybdopterin guanine dinucleotide Molybdopterin guanine dinucleotide is a member of the chemical class known as Purine Ribonucleoside Diphosphates. These are purine ribobucleotides with diphosphate group linked to the ribose moiety. It appears that the molybdopterin present in the nitrate reductase of a chlB mutant is converted to molybdopterin guanine dinucleotide during activation. (PMID 1459941) We propose therefore that MobB is an adapter protein that acts in concert with MobA to achieve the efficient biosynthesis and utilization of molybdopterin guanine dinucleotide. (PMID 12682065) <i>bis</i>-molybdopterin guanine dinucleotide Bis-molybdopterin guanine dinucleotide MGD Molybdopterin guanine dinucleotide Molybdopteringuaninedinucleotide MoO2(OH)Dtpp-mGDP MoO₂(OH)Dtpp-mGDP MPT-GMP C20H24N10O13P2S2 738.541 738.044095308 [({[3,4-dihydroxy-5-(6-hydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy][2-hydroxy-4-(4-hydroxy-2-imino-1,2,5,8-tetrahydropteridin-6-yl)-3,4-disulfanylidenebutoxy]phosphinic acid {[3,4-dihydroxy-5-(6-hydroxy-2-imino-3H-purin-9-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(2-hydroxy-4-(4-hydroxy-2-imino-5,8-dihydro-1H-pteridin-6-yl)-3,4-disulfanylidenebutoxy)phosphinic acid 128007-95-4 OC(COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1O)N1C=NC2=C1NC(=N)N=C2O)C(=S)C(=S)C1=CNC2=C(N1)C(O)=NC(=N)N2 InChI=1S/C20H24N10O13P2S2/c21-19-26-14-8(16(34)28-19)25-5(1-23-14)12(46)13(47)6(31)2-40-44(36,37)43-45(38,39)41-3-7-10(32)11(33)18(42-7)30-4-24-9-15(30)27-20(22)29-17(9)35/h1,4,6-7,10-11,18,25,31-33H,2-3H2,(H,36,37)(H,38,39)(H3,22,27,29,35)(H4,21,23,26,28,34) MNEQOJMCKOBWNR-UHFFFAOYSA-N Cytosol Cytosol logp -0.46 ALOGPS logs -3.48 ALOGPS solubility 2.46e-01 g/l ALOGPS logp -3 ChemAxon pka_strongest_acidic -4.5 ChemAxon pka_strongest_basic 15 ChemAxon iupac [({[3,4-dihydroxy-5-(6-hydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy][2-hydroxy-4-(4-hydroxy-2-imino-1,2,5,8-tetrahydropteridin-6-yl)-3,4-disulfanylidenebutoxy]phosphinic acid ChemAxon average_mass 738.541 ChemAxon mono_mass 738.044095308 ChemAxon smiles OC(COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1O)N1C=NC2=C1NC(=N)N=C2O)C(=S)C(=S)C1=CNC2=C(N1)C(O)=NC(=N)N2 ChemAxon formula C20H24N10O13P2S2 ChemAxon inchi InChI=1S/C20H24N10O13P2S2/c21-19-26-14-8(16(34)28-19)25-5(1-23-14)12(46)13(47)6(31)2-40-44(36,37)43-45(38,39)41-3-7-10(32)11(33)18(42-7)30-4-24-9-15(30)27-20(22)29-17(9)35/h1,4,6-7,10-11,18,25,31-33H,2-3H2,(H,36,37)(H,38,39)(H3,22,27,29,35)(H4,21,23,26,28,34) ChemAxon inchikey MNEQOJMCKOBWNR-UHFFFAOYSA-N ChemAxon polar_surface_area 351.03 ChemAxon refractivity 195.57 ChemAxon polarizability 64.66 ChemAxon rotatable_bond_count 12 ChemAxon acceptor_count 19 ChemAxon donor_count 13 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon guanylyl molybdenum cofactor biosynthesis The transition element molybdenum (Mo) has been long known as an essential micronutrient across the kingdoms of plants, animals, fungi and bacteria. However, molybdate itself is catalytically inactive and, with the exception of bacterial nitrogenase, needs to be activated through complexation by a special cofactor. There are several molybdenum cofactors, including molybdopterin (MPT), guanylyl molybdenum cofactor (MGD), cytidylyl molybdenum cofactor, or others [Rajagopalan92]. The chemical nature and biosynthesis of molybdenum cofactors have been investigated in detail in bacteria [Wuebbens95, Pitterle93, Pitterle93a, Rajagopalan92, SantamariaArauj04] and plants [Schwarz06]. All of the cofactors are synthesized from molybdopterin (MPT). The MPT structure is conserved in all organisms and it has been demonstrated that its biosynthesis is preserved in bacteria and plants alike. It is produced from GTP via cyclic pyranopterin phosphate (see molybdenum cofactor biosynthesis). The variability of the molybdenum cofactors found in bacteria is achieved by the attachment of GMP, AMP, IMP, or CMP to the phosphate group of MPT. In Escherichia coli, both guanylyl molybdenum cofactor and cytidylyl molybdenum cofactor are present. bis(molybdenum cofactor) synthase [multifunctional] catalyzes the transfer of the guanine nucleotide from GTP, releasing the β- and γ-phosphates of GTP as pyrophosphate and forming guanylyl molybdenum cofactor. (EcoCyc) PW002032 Metabolic guanylyl molybdenum cofactor biosynthesis PWY-5964 Specdb::CMs 1084247 Specdb::EiMs 5179 Specdb::NmrOneD 328532 Specdb::NmrOneD 328533 Specdb::NmrOneD 328534 Specdb::NmrOneD 328535 Specdb::NmrOneD 328536 Specdb::NmrOneD 328537 Specdb::NmrOneD 328538 Specdb::NmrOneD 328539 Specdb::NmrOneD 328540 Specdb::NmrOneD 328541 Specdb::NmrOneD 328542 Specdb::NmrOneD 328543 Specdb::NmrOneD 328544 Specdb::NmrOneD 328545 Specdb::NmrOneD 328546 Specdb::NmrOneD 328547 Specdb::NmrOneD 328548 Specdb::NmrOneD 328549 Specdb::NmrOneD 328550 Specdb::NmrOneD 328551 Specdb::MsMs 29300 Specdb::MsMs 29301 Specdb::MsMs 29302 Specdb::MsMs 35858 Specdb::MsMs 35859 Specdb::MsMs 35860 5486686 4589022 30404 CPD-582 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 van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. 17765195 McLuskey, K., Harrison, J. A., Schuttelkopf, A. W., Boxer, D. H., Hunter, W. N. (2003). "Insight into the role of Escherichia coli MobB in molybdenum cofactor biosynthesis based on the high resolution crystal structure." J Biol Chem 278:23706-23713. 12682065 Santini, C. L., Iobbi-Nivol, C., Romane, C., Boxer, D. H., Giordano, G. (1992). "Molybdoenzyme biosynthesis in Escherichia coli: in vitro activation of purified nitrate reductase from a chlB mutant." J Bacteriol 174:7934-7940. 1459941 Molybdopterin-guanine dinucleotide biosynthesis protein A P32173 MOBA_ECOLI mobA http://ecmdb.ca/proteins/P32173.xml Molybdopterin-guanine dinucleotide biosynthesis protein B P32125 MOBB_ECOLI mobB http://ecmdb.ca/proteins/P32125.xml Guanosine triphosphate + Hydrogen ion + Molybdopterin > Molybdopterin guanine dinucleotide + Pyrophosphate Hydrogen ion + molybdenum cofactor + Guanosine triphosphate <> Molybdopterin guanine dinucleotide + Pyrophosphate RXN0-262 Bis-molybdopterin guanine dinucleotide + Guanosine triphosphate + Hydrogen ion + Molybdopterin guanine dinucleotide > Guanylyl molybdenum cofactor + Pyrophosphate PW_R005942