N 6 -threonylcarbamoyladenosine

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Structural formula
Structural formula of N6-threonylcarbamoyladenosine
General
Surname N 6 -threonylcarbamoyladenosine
other names
  • t 6 A (short code)
  • N - {[(9-β- D -ribofuranosyl-9 H -purin-6-yl) amino] carbonyl} - L -threonine
Molecular formula C 15 H 20 N 6 O 8
External identifiers / databases
CAS number 24719-82-2
PubChem 161466
ChemSpider 141829
Wikidata Q15632802
properties
Molar mass 412.36 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 -Threonylcarbamoyladenosin (t 6 A) is a rare nucleoside and occurs in the tRNA . It consists of β- D- ribofuranose (sugar) and a substituted adenine . It differs from adenosine by adding a threonine linkedvia a carbamate . Like N 6 -isopentenyladenosine , it is found next to the anticodon at position 37 in the tRNA. These are those tRNAs thatreadthe codon ANN (where N represents the four nucleotides A, C, G and T), i.e. tRNA Ile , tRNA Thr , tRNA Asn , tRNA Lys , tRNA Ser and tRNA Arg .

A tRNA i Met from S. cerevisiae .
N 6 -Threonylcarbamoyladenosin here with t 6 A marked.

literature

  • GB Chheda: "Isolation and characterization of a novel nucleoside, N - [(9-beta-D-ribofuranosyl-9H-purin-6-yl) carbamoyl] threonine, from human urine", Life Sci. , 1969 , 8  (18), pp. 979-987 ( PMID 5346949 ).
  • Charles T. Lauhon: "Mechanism of N6-Threonylcarbamoyladenosine (t 6 A) Biosynthesis: Isolation and Characterization of the Intermediate Threonylcarbamoyl-AMP", Biochemistry , 2012 , 51  (44), pp. 8950-8963 ( doi : 10.1021 / bi301233d ) .

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. ↑ Christopher Deutsch, Basma El Yacoubi, Valérie de Crécy-Lagard, Dirk Iwata-Reuyl: "Biosynthesis of Threonylcarbamoyl Adenosine (t 6 A), a Universal tRNA Nucleoside", J Biol Chem , 2012 , 287  (17), p. 13666 -13673 ( doi : 10.1074 / jbc.M112.344028 , PMC 3340167 (free full text), PMID 22378793 ).
  4. ↑ Ludovic Perrochia, Estelle Crozat, Arnaud Hecker, Wenhua Zhang, Joseph Bareille, Bruno Collinet, Herman van Tilbeurgh, Patrick Forterre, Tamara Basta: "In vitro biosynthesis of a universal t 6 A tRNA modification in Archaea and Eukarya", Nucleic Acids Res , 2013 , 41  (3), pp. 1953-1964 ( doi : 10.1093 / nar / gks1287 , PMC 3561968 (free full text), PMID 23258706 ).
  5. ↑ Sarah E. Kolitz, Jon R. Lorsch: "Eukaryotic Initiator tRNA: Finely Tuned and Ready for Action", FEBS Letters , 2010 , 584  (2), pp. 396-404 ( doi : 10.1016 / j.febslet. 2009.11 . 047 , PMC 2795131 (free full text), PMID 19925799 ).

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