2-(Methylamino)-1H-purin-6(7H)-one  (Synonyms: N2-methylguanine)

2-(Methylamino)-1H-purin-6(7H)-one (N2-Methylguanine) is a modified nucleoside. 2-(Methylamino)-1H-purin-6(7H)-one is an endogenous methylated nucleoside found in human fluids.

2-(Methylamino)-1H-purin-6(7H)-one (N2-methylguanine) is found within both helical and looped regions of RNA secondary structure, and it can exist in either the s-cis or the s-trans rotamer. If there is a rotational preference for the methyl group, the effect of 2-(Methylamino)-1H-purin-6(7H)-one substitution may be specific to the sequence context depending upon which face of the base participates in hydrogen bonding^[1]. 2-(Methylamino)-1H-purin-6(7H)-one (N2-methylguanine) is the principal kinetic barrier for reverse transcription in the 1340 bases proximal to the 5' end of E. coli 16S rRNA. Transcription intermediates correspond to attenuation at the positions of 2-(Methylamino)-1H-purin-6(7H)-one in the rRNA sequence. The relaxation time for elongation of the cDNA through m2G is approximately 3 min^[2].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

165.15

C₆H₇N₅O

10030-78-1

Solid

Light yellow to khaki

O=C1N=C(NC)NC2=C1NC=N2

Room temperature in continental US; may vary elsewhere.

• [1]. Rife JP, et al. N 2-methylguanosine is iso-energetic with guanosine in RNA duplexes and GNRA tetraloops. Nucleic Acids Res. 1998 Aug 15;26(16):3640-4.  [Content Brief]

  [2]. Youvan DC, et al. Reverse transcriptase pauses at N2-methylguanine during in vitro transcription of Escherichia coli 16S ribosomal RNA. Proc Natl Acad Sci U S A. 1979 Aug;76(8):3751-4.  [Content Brief]