N 6 -isopentenyladenosine

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Structural formula
Structural formula of N6-isopentenyladenosine
General
Surname N 6 -isopentenyladenosine
other names
  • i 6 A (short code)
  • N 6 - (Δ 2 -isopentenyl) adenosine
  • Riboprin
  • 9-β- D -ribofuranosyl-3-methylbut-2-enyl-adenine
  • 9 - [(2 R , 3 R , 4 S , 5 R ) -3,4-dihydroxy-5- (hydroxymethyl) oxolan-2-yl] -3-methylbut-2-enylamino-purine
Molecular formula C 15 H 21 N 5 O 4
External identifiers / databases
CAS number 7724-76-7
EC number 231-771-3
ECHA InfoCard 100,028,884
PubChem 24405
ChemSpider 22815
DrugBank DB11933
Wikidata Q973089
properties
Molar mass 335.36 g mol −1
Physical state

firmly

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 6 -isopentenyladenosine (i 6 A, riboprin ) is a rare nucleoside and occurs in the tRNA . It consists of β- D- ribofuranose (sugar) and N 6 -isopentenyladenine . It differs from adenosine by adding an isopentenyl group on the amino group . The adenosine is converted with isopentenyl pyrophosphate by means of the tRNA isopentenyl transferase to form N 6 -isopentenyl adenosine. Like N 6 -threonylcarbamoyladenosine , it is found in addition to the anticodon at position 37 in tRNA in both bacteria and eukaryotes .

A tRNA Sec from Escherichia coli .
N 6 -isopentenyladenosine is marked with i 6 A here .

literature

  • Michel Laloue, Claude Terrine, Jean Guern: "Cytokinins: Metabolism and Biological Activity of N 6 - (Δ 2 -Isopentenyl) adenosine and N 6 - (Δ 2 -Isopentenyl) adenine in Tobacco Cells and Callus", Plant Physiol. , 1977 , 59 , pp. 478-483 ( full text ).
  • Maurizio Bifulco, Anna Maria Malfitano, Maria Chiara Proto, Antonietta Santoro, Maria Gabriella Caruso, Chiara Laezza: "Biological and Pharmacological Roles of N6-Isopentenyladenosine: An Emerging Anticancer Drug", Anti-Cancer Agents in Medicinal Chemistry , 2008 , 8  (2 ), Pp. 200-204 ( PMID 18288922 , doi : 10.2174 / 187152008783497028 ).

Individual evidence

  1. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
  2. ↑ 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 ).
  3. ↑ Larry K. Kline, Fritz Fittler, Ross H. Hall: “ N 6 - (Δ 2 -Isopentenyl) adenosine. Biosynthesis in Transfer Ribonucleic Acid in Vitro “, Biochemistry , 1969 , 8  (11), pp. 4361-4371 ( PMID 4311031 ; doi : 10.1021 / bi00839a021 ).
  4. ↑ Nadja Rosenbaum, Malcolm L. Gefter: “Δ 2 -Isopentenylpyrophosphate: Transfer Ribonucleic Acid Δ 2 -Isopentenyltransferase from Escherichia coli . Purification and Properties of the Enzyme ", J. Biol. Chem. , 1972 , 247  (18), pp. 5675-5680 ( PMID 4341485 ; Abstract ; PDF ).
  5. ↑ BC Persson, B. Esberg, O. Olafsson, GR Björk: “Synthesis and function of isopentenyl adenosine derivatives in tRNA”, Biochimie , 1994 , 76  (12), pp. 1152-1160 ( PMID 7748950 , doi : 10.1016 / 0300 -9084 (94) 90044-2 ).

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