N 2 , N 2 -dimethylguanosine

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Structural formula
Structural formula of N2, N2-dimethylguanosine
General
Surname N 2 , N 2 -dimethylguanosine
other names
  • m 2 2 G (short code)
  • 9-β- D -ribofuranosyl- N 2 , N 2 -dimethylguanine
  • 9 - [(2 R , 3 R , 4 S , 5 R ) -3,4-dihydroxy-5- (hydroxymethyl) oxolan-2-yl] -2-dimethylamino-1 H -purin-6-one
Molecular formula C 12 H 17 N 5 O 5
External identifiers / databases
CAS number 2140-67-2
PubChem 135501639
ChemSpider 83878
Wikidata Q27109160
properties
Molar mass 311.29 g mol −1
Physical state

firmly

Melting point

235-236 ° C

safety instructions
GHS hazard labeling
no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

N 2 , N 2 -dimethylguanosine (m 2 2 G) is a rare nucleoside and occurs in tRNA and rRNA . It consists of β- D- ribofuranose (sugar) and N 2 , N 2 -dimethylguanine . It is a derivative of guanosine , which isdoubly methylated at the amino group .

Further dimethylated nucleobases are N 4 , N 4 -dimethylcytidine and N 6 , N 6 -dimethyladenosine .

properties

For example, it sits in the tRNA Ala and tRNA Tyr - mostly in position 26 - as a “hinge” between the dihydrouracil arm and the anticodon arm. The guanine is modified by N 2 , N 2 -dimethylguanosine-tRNA-methyltransferases ( EC  2.1.1.213 , EC  2.1.1.215 , EC  2.1.1.216 ). The methyl group is provided by S-adenosyl methionine .

A tRNA Ala from S. cerevisiae . N 2 , N 2 -Dimethylguanosin is here m 2 2 G in.

Because of the double methylation in the 2-position, base pairing with cytosine is not possible. However, a pairing with the opposite adenine in position 44 is possible.

In contrast to other nucleosides, N 2 , N 2 -dimethylguanosine is not broken down into uric acid , but excreted unchanged in the urine.

Web links

Commons : N (2), N (2) -dimethylguanosine tRNA methyltransferase Trm1  - Collection of pictures, videos and audio files

Individual evidence

  1. ↑ Entry on N 2 , N 2 -Dimethylguanosine in the Human Metabolome Database (HMDB) , accessed on October 12, 2013.
  2. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
  3. ↑ Patrick A. Limbach, Pamela F. Crain, James A. McCloskey: "Summary: the modified nucleosides of RNA", Nucleic Acids Research , 1994 , 22  (12), pp. 2183-2196 ( doi : 10.1093 / nar / 22.12 .2183 , PMC 523672 (free full text), PMID 7518580 ).
  4. ^ Robert W. Holley , Jean Apgar, George A. Everett, James T. Madison, Mark Marquisee, Susan H. Merrill, John Robert Penswick, Ada Zamir: "Structure of a Ribonucleic Acid", Science , 1965 , 147 , pp. 1462-1465 ( doi : 10.1126 / science.147.3664.1462 ).
  5. ^ Robert W. Holley, "The Nucleotide Sequence of a Nucleic Acid," Scientific American , February 1966, 214 , pp. 30-39.
  6. ^ BP Doctor, Judith E. Loebel, Mary Ann Sodd, David B. Winter: "Nucleotide Sequence of Escherichia coli Tyrosine Transfer Ribonucleic Acid", Science , 1969 , 163 , pp. 693-695 ( doi : 10.1126 / science.163.3868. 693 ).
  7. ↑ J. Edqvist, H. Grosjean, KB Stråby: "Identity elements for N 2 -dimethylation of guanosine-26 in yeast tRNAs", Nucleic Acids Res. , 1992 , 20  (24), pp. 6575-6581 ( PMC 334573 ( free full text); PMID 1480477 ).
  8. ↑ Armengaud, J., Urbonavicius, J., Fernandez, B., Chaussinand, G., Bujnicki, JM, Grosjean, H .: N 2 -methylation of guanosine at position 10 in tRNA is catalyzed by a THUMP domain-containing, S -adenosylmethionine-dependent methyltransferase, conserved in Archaea and Eukaryota . In: J. Biol. Chem. . 279, 2004, pp. 37142-37152. PMID 15210688 .
  9. ↑ Awai, T., Kimura, S., Tomikawa, C., Ochi, A., Ihsanawati, Bessho, Y., Yokoyama, S., Ohno, S., Nishikawa, K., Yokogawa, T., Suzuki, T., Hori, H .: Aquifex aeolicus tRNA ( N 2 , N 2 -guanine) -dimethyltransferase (Trm1) catalyzes transfer of methyl groups not only to guanine 26 but also to guanine 27 in tRNA . In: J. Biol. Chem. . 284, 2009, pp. 20467-20478. PMID 19491098 .
  10. ↑ Constantinesco, F., Motorin, Y., Grosjean, H .: Characterization and enzymatic properties of tRNA (guanine 26 , N 2 , N 2 -dimethyltransferase (Trm1p) from Pyrococcus furiosus . In: J. Mol. Biol . 291 , 1999, pp. 375-392 PMID 10438627 .
  11. ↑ Constantinesco, F., Benachenhou, N., Motorin, Y., Grosjean, H .: The tRNA (guanine-26, N 2 - N 2 ) methyltransferase (Trm1) from the hyperthermophilic archaeon Pyrococcus furiosus : cloning, sequencing of the gene and its expression in Escherichia coli . In: Nucleic Acids Res . 26, 1998, pp. 3753-3761. PMID 9685492 .
  12. ↑ Liu, J., Liu, J., Straby, KB: Point and deletion mutations eliminate one or both methyl group transfers catalysed by the yeast TRM1 encoded tRNA (m 2 2 G 26 ) dimethyltransferase . In: Nucleic Acids Res . 26, 1998, pp. 5102-5108. PMID 9801306 .
  13. ↑ Liu, J., Zhou, GQ, Straby, KB: Caenorhabditis elegans ZC376.5 encodes a tRNA (m 2 2 G 26 ) dimethyltransferance in which 246 arginine is important for the enzyme activity . In: Genes . 226, 1999, pp. 73-81. PMID 10048958 .
  14. ↑ Pradeep S. Pallan, Christoph Kreutz, Silvia Bosio, Ronald Micura, Martin Egli: "Effects of N 2 , N 2 -dimethylguanosine on RNA structure and stability: Crystal structure of an RNA duplex with tandem m 2 2 G: A pairs" , RNA , 2008 , 14 , pp. 1-11 ( doi : 10.1261 / rna.1078508 ; PDF ).
  15. ↑ Rüdiger Hörbelt (Diss.): "Detection, isolation and characterization of N 2 , N 2 -dimethylguanosine as an inhibiting factor of Ca 2+ -ATPase in chronic renal failure", Ruhr University, Bochum 1998 ( PDF ; 332 kB).