2.0 2012-05-31 13:53:37 -0600 2015-09-17 15:41:12 -0600 ECMDB01495 M2MDB000403 Queuine Queuine is a member of the chemical class known as Aminocyclitols and Derivatives. These are cyclitols with at least one hydroxyl group replace by an amino group. Queuine (Q) is a hypermodified base found in the first (or wobble) position of the anticodon of tRNAs specific for Asn, Asp, His, and Tyr, in most eukaryotes and prokaryotes. The nucleoside of queuine is queuosine. Queuine is not found in the tRNA of archaea; however, a related 7-deazaguanine derivative, the nucleoside of which is archaeosine, occurs in different tRNA position, the dihydrouridine loop, and in tRNAs with more specificities. (WikiPedia) 2-Amino-5-((((1S,4S,5R)-4,5-dihydroxy-2-cyclopenten-1-yl)amino)methyl)-1,7-dihydro-4H-pyrrolo(2,3-D)pyrimidin-4-one 7-(3,4-trans-4,5-cis-Dihydroxy-1-cyclopenten-3-ylaminomethyl)-7-deazaguanine 7AMe7DAGua Base Q Queuine C12H15N5O3 277.2792 277.117489371 (1R,2S,5S)-5-[({4-hydroxy-2-imino-1H,2H,7H-pyrrolo[2,3-d]pyrimidin-5-yl}methyl)amino]cyclopent-3-ene-1,2-diol (1R,2S,5S)-5-[({4-hydroxy-2-imino-1H,7H-pyrrolo[2,3-d]pyrimidin-5-yl}methyl)amino]cyclopent-3-ene-1,2-diol 72496-59-4 O[C@@H]1C=C[C@@H](NCC2=CNC3=C2C(=O)NC(=N)N3)[C@@H]1O InChI=1S/C12H15N5O3/c13-12-16-10-8(11(20)17-12)5(4-15-10)3-14-6-1-2-7(18)9(6)19/h1-2,4,6-7,9,14,18-19H,3H2,(H4,13,15,16,17,20)/t6-,7-,9+/m1/s1 WYROLENTHWJFLR-BHNWBGBOSA-N Cytosol logp -1.16 ALOGPS logs -2.90 ALOGPS solubility 3.48e-01 g/l ALOGPS logp -1.2 ChemAxon pka_strongest_acidic 7.48 ChemAxon pka_strongest_basic 8.08 ChemAxon iupac (1R,2S,5S)-5-[({4-hydroxy-2-imino-1H,2H,7H-pyrrolo[2,3-d]pyrimidin-5-yl}methyl)amino]cyclopent-3-ene-1,2-diol ChemAxon average_mass 277.2792 ChemAxon mono_mass 277.117489371 ChemAxon smiles O[C@@H]1C=C[C@@H](NCC2=CNC3=C2C(=O)NC(=N)N3)[C@@H]1O ChemAxon formula C12H15N5O3 ChemAxon inchi InChI=1S/C12H15N5O3/c13-12-16-10-8(11(20)17-12)5(4-15-10)3-14-6-1-2-7(18)9(6)19/h1-2,4,6-7,9,14,18-19H,3H2,(H4,13,15,16,17,20)/t6-,7-,9+/m1/s1 ChemAxon inchikey WYROLENTHWJFLR-BHNWBGBOSA-N ChemAxon polar_surface_area 136.75 ChemAxon refractivity 83.97 ChemAxon polarizability 27.42 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 7 ChemAxon donor_count 7 ChemAxon physiological_charge 2 ChemAxon formal_charge 0 ChemAxon preQ0 metabolism PreQ0 or 7-cyano-7-carbaguanine is biosynthesized by degrading GTP. GTP first interacts with water through a GTP cyclohydrolase resulting in the release of a formate, a hydrogen ion and a 7,8-dihydroneopterin 3'-triphosphate. The latter compound then interacts with water through a 6-carboxy-5,6,7,8-tetrahydropterin synthase resulting in a acetaldehyde, triphosphate, 2 hydrogen ion and 6-carboxy-5,6,7,8-tetrahydropterin. The latter compound then reacts spontaneously with a hydrogen ion resulting in the release of a ammonium molecule and a 7-carboxy-7-deazaguanine. This compound then interacts with ATP and ammonium through 7-cyano-7-deazaguanine synthase resulting in the release of water, phosphate, ADP, hydrogen ion and a 7-cyano-7-carbaguanine. The degradation of 7-cyano-7-deazaguanine can lead to produce a preQ1 or a queuine by reacting with 3 hydrogen ions and 2 NADPH through a 7-cyano-7-deazaguanine reductase. PreQ1 then interacts with a guanine 34 in tRNA through a tRNA-guanine transglycosylase resulting in a release of a guanine and a 7-aminomethyl-7-deazaguanosine 34 in tRNA. This nucleic acid then interacts with SAM through a S-adenosylmethionine tRNA ribosyltransferase-isomerase resulting in a release of a hydrogen ion, L-methionine, adenine and an epoxyqueuosine PW001893 Metabolic Specdb::MsMs 26027 Specdb::MsMs 26028 Specdb::MsMs 26029 Specdb::MsMs 32585 Specdb::MsMs 32586 Specdb::MsMs 32587 HMDB01495 1034 C01449 17433 QEI Queuine 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 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 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 Queuine tRNA-ribosyltransferase P0A847 TGT_ECOLI tgt http://ecmdb.ca/proteins/P0A847.xml NADPH-dependent 7-cyano-7-deazaguanine reductase Q46920 QUEF_ECOLI queF http://ecmdb.ca/proteins/Q46920.xml 3 Hydrogen ion + 2 NADPH + 7-Cyano-7-carbaguanine >2 NADP + Queuine Guanine(34) in tRNA + Queuine > queuosine(34) in tRNA + Guanine Queuine + 7-Aminomethyl-7-carbaguanine <> Guanine R03789 7-Cyano-7-carbaguanine + 3 Hydrogen ion + 2 NADPH + 2 NADPH > Queuine +2 NADP + Queuine PW_R005182 Queuine + 7 7-Aminomethyl-7-carbaguanine <> Guanine Queuine + 7 7-Aminomethyl-7-carbaguanine <> Guanine