N 6 , N 6 -dimethyladenine

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Structural formula
Structural formula of N6, N6-dimethyladenine
General
Surname N 6 , N 6 -dimethyladenine
other names
  • 6-dimethylaminopurine
  • 6-DMAP
Molecular formula C 7 H 9 N 5
Brief description

white crystals

External identifiers / databases
CAS number 938-55-6
EC number 213-344-3
ECHA InfoCard 100.012.131
PubChem 3134
ChemSpider 3022
Wikidata Q15632695
properties
Molar mass 163.18 g mol −1
Physical state

firmly

Melting point

259-262 ° C

solubility

soluble in water

safety instructions
GHS labeling of hazardous substances
no GHS pictograms
H and P phrases H: no H-phrases
P: no P-phrases
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

N 6 , N 6 -Dimethyladenine ( 6-dimethylaminopurine ) is a heterocyclic organic compound with a purine backbone. It is a derivative of the nucleobase adenine , which isdoubly methylated at the amino group . It occurs as a component of the nucleoside N 6 , N 6 -dimethyladenosine  (m 6 2 G) in the rRNA . It is also a hydrolysis product of puromycin .

Further dimethylated nucleobases are N 2 , N 2 -dimethylguanine and N 4 , N 4 -dimethylcytosine .

literature

  • Andreas BJ Parusel, Wolfgang Rettig, Krystyna Rotkiewicz: "Spectroscopic and Theoretical Studies of 6-N, N-Dimethyladenine", J. Phys. Chem. A , 2002 , 106  (10), pp. 2293-2299 ( doi : 10.1021 / jp012632t ).

Individual evidence

  1. ↑ a b c B. R. Baker, Joseph P. Joseph, Robert E. Schaub: “Puromycin. Synthetic studies. I. Synthesis of 6-dimethylaminopurine, a hydrolytic fragment ", Journal of Organic Chemistry , 1954 , 19 , pp. 631-637 ( doi : 10.1021 / jo01369a024 ).
  2. ↑ a b c Data sheet 6- (Dimethylamino) purine from Sigma-Aldrich , accessed on May 1, 2014 ( PDF ).
  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 ).

Web links