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Pathway Description
PreQ0 Metabolism
Escherichia coli
Category:
Metabolite Pathway
Sub-Category:
Metabolic
Created: 2015-09-10
Last Updated: 2019-09-12
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
References
PreQ0 Metabolism References
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Pubmed: 12697167
McCarty RM, Bandarian V: Deciphering deazapurine biosynthesis: pathway for pyrrolopyrimidine nucleosides toyocamycin and sangivamycin. Chem Biol. 2008 Aug 25;15(8):790-8. doi: 10.1016/j.chembiol.2008.07.012.
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McCarty RM, Somogyi A, Lin G, Jacobsen NE, Bandarian V: The deazapurine biosynthetic pathway revealed: in vitro enzymatic synthesis of PreQ(0) from guanosine 5'-triphosphate in four steps. Biochemistry. 2009 May 12;48(18):3847-52. doi: 10.1021/bi900400e.
Pubmed: 19354300
Blaise M, Becker HD, Lapointe J, Cambillau C, Giege R, Kern D: Glu-Q-tRNA(Asp) synthetase coded by the yadB gene, a new paralog of aminoacyl-tRNA synthetase that glutamylates tRNA(Asp) anticodon. Biochimie. 2005 Sep-Oct;87(9-10):847-61. doi: 10.1016/j.biochi.2005.03.007. Epub 2005 Apr 8.
Pubmed: 16164993
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Pubmed: 8494901
El Yacoubi B, Bailly M, de Crecy-Lagard V: Biosynthesis and function of posttranscriptional modifications of transfer RNAs. Annu Rev Genet. 2012;46:69-95. doi: 10.1146/annurev-genet-110711-155641. Epub 2012 Aug 16.
Pubmed: 22905870
Garcia GA, Koch KA, Chong S: tRNA-guanine transglycosylase from Escherichia coli. Overexpression, purification and quaternary structure. J Mol Biol. 1993 May 20;231(2):489-97. doi: 10.1006/jmbi.1993.1296.
Pubmed: 8323579
Harada F, Nishimura S: Possible anticodon sequences of tRNA His , tRNA Asm , and tRNA Asp from Escherichia coli B. Universal presence of nucleoside Q in the first postion of the anticondons of these transfer ribonucleic acids. Biochemistry. 1972 Jan 18;11(2):301-8.
Pubmed: 4550561
Meier F, Suter B, Grosjean H, Keith G, Kubli E: Queuosine modification of the wobble base in tRNAHis influences 'in vivo' decoding properties. EMBO J. 1985 Mar;4(3):823-7.
Pubmed: 2988936
Miles ZD, McCarty RM, Molnar G, Bandarian V: Discovery of epoxyqueuosine (oQ) reductase reveals parallels between halorespiration and tRNA modification. Proc Natl Acad Sci U S A. 2011 May 3;108(18):7368-72. doi: 10.1073/pnas.1018636108. Epub 2011 Apr 18.
Pubmed: 21502530
Slany RK, Bosl M, Crain PF, Kersten H: A new function of S-adenosylmethionine: the ribosyl moiety of AdoMet is the precursor of the cyclopentenediol moiety of the tRNA wobble base queuine. Biochemistry. 1993 Aug 3;32(30):7811-7.
Pubmed: 8347586
Slany RK, Bosl M, Kersten H: Transfer and isomerization of the ribose moiety of AdoMet during the biosynthesis of queuosine tRNAs, a new unique reaction catalyzed by the QueA protein from Escherichia coli. Biochimie. 1994;76(5):389-93.
Pubmed: 7849103
Urbonavicius J, Qian Q, Durand JM, Hagervall TG, Bjork GR: Improvement of reading frame maintenance is a common function for several tRNA modifications. EMBO J. 2001 Sep 3;20(17):4863-73. doi: 10.1093/emboj/20.17.4863.
Pubmed: 11532950
Van Lanen SG, Reader JS, Swairjo MA, de Crecy-Lagard V, Lee B, Iwata-Reuyl D: From cyclohydrolase to oxidoreductase: discovery of nitrile reductase activity in a common fold. Proc Natl Acad Sci U S A. 2005 Mar 22;102(12):4264-9. doi: 10.1073/pnas.0408056102. Epub 2005 Mar 14.
Pubmed: 15767583
Vinayak M, Pathak C: Queuosine modification of tRNA: its divergent role in cellular machinery. Biosci Rep. 2009 Nov 23;30(2):135-48. doi: 10.1042/BSR20090057.
Pubmed: 19925456
Katzenmeier G, Schmid C, Kellermann J, Lottspeich F, Bacher A: Biosynthesis of tetrahydrofolate. Sequence of GTP cyclohydrolase I from Escherichia coli. Biol Chem Hoppe Seyler. 1991 Nov;372(11):991-7.
Pubmed: 1665332
Schmid C, Meining W, Weinkauf S, Bachmann L, Ritz H, Eberhardt S, Gimbel W, Werner T, Lahm HW, Nar H, et al.: Studies on GTP cyclohydrolase I of Escherichia coli. Adv Exp Med Biol. 1993;338:157-62. doi: 10.1007/978-1-4615-2960-6_30.
Pubmed: 8304099
Blattner FR, Plunkett G 3rd, Bloch CA, Perna NT, Burland V, Riley M, Collado-Vides J, Glasner JD, Rode CK, Mayhew GF, Gregor J, Davis NW, Kirkpatrick HA, Goeden MA, Rose DJ, Mau B, Shao Y: The complete genome sequence of Escherichia coli K-12. Science. 1997 Sep 5;277(5331):1453-62. doi: 10.1126/science.277.5331.1453.
Pubmed: 9278503
McCarty RM, Somogyi A, Bandarian V: Escherichia coli QueD is a 6-carboxy-5,6,7,8-tetrahydropterin synthase. Biochemistry. 2009 Mar 24;48(11):2301-3. doi: 10.1021/bi9001437.
Pubmed: 19231875
Hayashi K, Morooka N, Yamamoto Y, Fujita K, Isono K, Choi S, Ohtsubo E, Baba T, Wanner BL, Mori H, Horiuchi T: Highly accurate genome sequences of Escherichia coli K-12 strains MG1655 and W3110. Mol Syst Biol. 2006;2:2006.0007. doi: 10.1038/msb4100049. Epub 2006 Feb 21.
Pubmed: 16738553
Gaur R, Varshney U: Genetic analysis identifies a function for the queC (ybaX) gene product at an initial step in the queuosine biosynthetic pathway in Escherichia coli. J Bacteriol. 2005 Oct;187(20):6893-901. doi: 10.1128/JB.187.20.6893-6901.2005.
Pubmed: 16199558
Reuter K, Slany R, Ullrich F, Kersten H: Structure and organization of Escherichia coli genes involved in biosynthesis of the deazaguanine derivative queuine, a nutrient factor for eukaryotes. J Bacteriol. 1991 Apr;173(7):2256-64. doi: 10.1128/jb.173.7.2256-2264.1991.
Pubmed: 1706703
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