Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2002 Mar 1;30(5):1124-31.
doi: 10.1093/nar/30.5.1124.

Chemical incorporation of 1-methyladenosine into oligonucleotides

Sergey N Mikhailov  1 , Jef Rozenski, Ekaterina V Efimtseva, Roger Busson, Arthur Van Aerschot, Piet Herdewijn
Affiliations

Chemical incorporation of 1-methyladenosine into oligonucleotides

Sergey N Mikhailov et al. Nucleic Acids Res. .

Abstract

The base moiety of 1-N-methyladenosine can be protected with a chloroacetyl group for incorporation of this modified nucleoside into DNA and RNA. Carefully controlled anhydrous conditions are needed for deprotection of the oligonucleotides.

PubMed Disclaimer

Figures

Figure 1
Figure 1
Capillary LC-MS analysis of the oligonucleotides obtained by enzymatic hydrolysis of the 17mer with RNase T1. (A–C) Reconstructed ion chromatograms for the theoretical m/z values and (D) UV trace at 260 nm with annotation of the other components. >p indicates a cyclic phosphate at the 3′-end.
Figure 2
Figure 2
–ESI fragment ion spectra of the m/z 148 fragment recorded with collision energy set at 20 eV for (A) the base released from 5′-CCAGGAUCGm1AAACCUGG-3′ with 85 V cone voltage, (B) the m1A base anion released from 1-methyladenosine with 50 V cone voltage and (C) the m6A base anion released from 6-methyladenosine with 50 V cone voltage.
None
Scheme 1. (a) MMTrCl/Py; (b) TMSCl/Py; (c) BzCl or Ac2O or (ClCH2CO)2O/Py; (d) MeNH2 or EtNH2/MeOH; (e) tBuMe2SiCl-imidazole.
See this image and copyright information in PMC

Similar articles

See all similar articles

Cited by

See all "Cited by" articles

References

    1. Rozenski J., Crain,P.F. and McCloskey,J. (1999) The RNA modification database: 1999 update. Nucleic Acids Res., 27, 196–197. - PMC - PubMed
    1. Agris P.F. (1996) The importance of being modified: roles of modified nucleosides and Mg2+ in RNA structure and function. Prog. Nucleic Acid Res. Mol. Biol., 53, 79–129. - PubMed
    1. Gesteland R.F. and Atkins,J.F. (eds) (1993) The RNA World. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY.
    1. Helm M., Brulé,H., Degoul,F., Cepanec,C., Leroux,J.-P., Giegé,R. and Florentz,C. (1998) The presence of modified nucleotides is required for cloverleaf folding of a human mitochondrial tRNA. Nucleic Acids Res., 26, 1636–1343. - PMC - PubMed
    1. Anderson J., Phan,L. and Hinnebusch,A.G. (2000) The Gcd10p/Gcd14p complex is the essential two-subunit tRNA (1-methyladenosine) methyltransferase of Saccharomyces cerevisiae. Proc. Natl Acad. Sci. USA, 97, 5173–5178. - PMC - PubMed

Publication types

MeSH terms