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. 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.

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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

References

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