1-Méthylguanosine

Identification
1-Méthylguanosine

Structure de la 1-Méthylguanosine
Nom UICPA	1-méthylguanosine
Synonymes	m¹G
N^o CAS	2140-65-0
N^o ECHA	100.159.022
N^o CE	630-718-5
PubChem	96373
ChEBI	19062
SMILES	Cn1c(N)nc2n(cnc2c1=O)[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O PubChem, vue 3D
InChI	Std. InChI : vue 3D InChI=1S/C11H15N5O5/c1-15-9(20)5-8(14-11(15)12)16(3-13-5)10-7(19)6(18)4(2-17)21-10/h3-4,6-7,10,17-19H,2H2,1H3,(H2,12,14)/t4-,6-,7-,10-/m1/s1 Std. InChIKey : UTAIYTHAJQNQDW-KQYNXXCUSA-N
Propriétés chimiques
Formule	C₁₁H₁₅N₅O₅ [Isomères]
Masse molaire^[1]	297,267 3 ± 0,012 4 g/mol C 44,44 %, H 5,09 %, N 23,56 %, O 26,91 %,

Unités du SI et CNTP, sauf indication contraire.
modifier

La 1-méthylguanosine (m¹G) est un nucléoside dont la base nucléique est un dérivé méthylé de la guanine, l'ose étant le β-D-ribofuranose. Elle est présente naturellement dans certains ARN de transfert et ARN ribosomiques^[2] ; un résidu de m¹G se trouve par exemple en position 9 de l'ARNt^Ala, entre le bras accepteur et le bras du dihydrouracile^[3] :

ARNt d'alanine chez la levure.
La 1-méthylguanosine est notée m¹G.

La méthylation de la guanine sur l'atome d'azote 1 rend impossible la formation d'une paire de bases Watson-Crick.

Notes et références

↑ Masse molaire calculée d’après « Atomic weights of the elements 2007 », sur www.chem.qmul.ac.uk.
↑ (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) Robert W. Holley, Jean Apgar, George A. Everett, James T. Madison, Mark Marquisee, Susan H. Merrill, John Robert Penswick et Ada Zamir, « Structure of a Ribonucleic Acid », Science, vol. 147, n^o 3664,‎ 19 mars 1965, p. 1462-1465 (PMID 14263761, DOI 10.1126/science.147.3664.1462, Bibcode 1965Sci...147.1462H, 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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