2-Méthyladénosine

Identification
2-Méthyladénosine

Structure de la 2-méthyladénosine
Nom UICPA	2-méthyladénosine
Synonymes	m²A
N^o CAS	16526-56-0
PubChem	459890
ChEBI	19688
SMILES	Cc1nc(N)c2ncn([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)c2n1 PubChem, vue 3D
InChI	Std. InChI : vue 3D InChI=1S/C11H15N5O4/c1-4-14-9(12)6-10(15-4)16(3-13-6)11-8(19)7(18)5(2-17)20-11/h3,5,7-8,11,17-19H,2H2,1H3,(H2,12,14,15)/t5-,7-,8-,11-/m1/s1 Std. InChIKey : IQZWKGWOBPJWMX-IOSLPCCCSA-N
Propriétés chimiques
Formule	C₁₁H₁₅N₅O₄ [Isomères]
Masse molaire^[1]	281,267 9 ± 0,012 1 g/mol C 46,97 %, H 5,38 %, N 24,9 %, O 22,75 %,

Unités du SI et CNTP, sauf indication contraire.
modifier

La 2-méthyladénosine (m²A) est un nucléoside dont la base nucléique est la 2-méthyladénine, un dérivé méthylé de l'adénine, l'ose étant le β-D-ribofuranose. Son observation a été publiée pour la première fois en 1972^[2]. Elle est présente naturellement dans certains ARN de transfert et ARN ribosomiques^[3], par exemple en position 38 dans l'ARNt^Arg^[4].

Notes et références

↑ Masse molaire calculée d’après « Atomic weights of the elements 2007 », sur www.chem.qmul.ac.uk.
↑ (en) Mineo Saneyoshi, Ziro Ohashi, Fumio Harada et Susumu Nishimura, « Isolation and characterization of 2-methyladenosine from Escherichia coli tRNA^Glu₂, tRNA^Asp₁, tRNA^His₁ and tRNA^Arg », Biochimica et Biophysica Acta (BBA) - Nucleic Acids and Protein Synthesis, vol. 262, n^o 1,‎ 23 février 1972, p. 1-10 (PMID 4552900, DOI 10.1016/0005-2787(72)90212-2, lire en ligne)
↑ (en) Patrick A. Limbach, Pamela F. Crain et James A. McCloskey, « Summary: the modified nucleosides of RNA », Nucleic Acids Research, vol. 22, n^o 12,‎ 25 juin 1994, p. 2183-2196 (PMID 7518580, PMCID 523672, DOI 10.1093/nar/22.12.2183, lire en ligne)
↑ (en) Kalpana Chakraburtty, « Primary structure of tRNA_II^Arg of E. coli B », Nucleic Acids Research, vol. 2, n^o 10,‎ octobre 1975, p. 1787-1792 (PMID 1103085, PMCID 343546, DOI 10.1093/nar/2.10.1787, lire en ligne)

v · m

Acides nucléiques

Bases nucléiques

Nucléosides

Ribonucléosides	Adénosine (A) Ribothymidine (T, m⁵U) Uridine (U) Guanosine (G) Cytidine (C) Inosine (I) Xanthosine (X) Queuosine (Q)
Désoxyribonucléosides	Désoxyadénosine Thymidine Désoxyuridine Désoxyguanosine Désoxycytidine
Nucléosides modifiés	Pseudouridine (ψ) Dihydrouridine (D) m¹A m²A m⁶A m⁶₂A i⁶A t⁶A A_m Ar(p) DHT m³U mo⁵U s²U s⁴U iG m¹G m²G m²₂G G_m k²C iC ψC ψiC m³C m⁴C m⁵C m⁴₂C C_m ac⁴C s²C m¹I I_m Archéosine (G*)

Nucléotides

Ribonucléotides	Monophosphate AMP m⁵UMP UMP GMP CMP IMP XMP Diphosphate ADP m⁵UDP UDP GDP CDP IDP XDP Triphosphate ATP m⁵UTP UTP GTP CTP ITP XTP Cycliques AMPc GMPc di-GMPc ADPRc
Désoxyribonucléotides	Monophosphate dAMP TMP dUMP dGMP dCMP Diphosphate dADP TDP dUDP dGDP dCDP Triphosphate dATP TTP dUTP dGTP dCTP
Acides nucléiques	ADN ADNn ADNmt ADN chloroplastique ADNc ARN ARNm ARN non codant miARN ARN circulaire ARNr ARNt shARN pARNi pARNn ARNpi snoARN ARNsn 7SK ARNtm Oligonucléotide Liste de différents types d'ADN Liste de différents types d'ARN

Analogues
non ribosidiques

Vecteurs de clonage

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