PMID- 23425279
OWN - NLM
STAT- MEDLINE
DCOM- 20130509
LR  - 20131121
IS  - 1520-4995 (Electronic)
IS  - 0006-2960 (Linking)
VI  - 52
IP  - 11
DP  - 2013 Mar 19
TI  - Base pairing and miscoding properties of 1,N(6)-ethenoadenine- and 
      3,N(4)-ethenocytosine-containing RNA oligonucleotides.
PG  - 1990-7
LID - 10.1021/bi400116y [doi]
AB  - Two RNA phosphoramidites containing the bases 1,N(6)-ethenoadenine (epsilonA) and 
      3,N(4)-ethenocytosine (epsilonC) were synthesized. These building blocks were 
      incorporated into two 12-mer oligoribonucleotides for evaluation of the base 
      pairing properties of these base lesions by UV melting curve (Tm) and circular 
      dichroism measurements. The Tm data of the resulting duplexes with the etheno 
      modifications opposing all natural bases showed a substantial destabilization 
      compared to the corresponding natural duplexes, confirming their inability to 
      form base pairs. The coding properties of these lesions were further investigated 
      by introducing them into 31-mer oligonucleotides and assessing their ability to 
      serve as templates in primer extension reactions with HIV, AMV, and MMLV reverse 
      transcriptases (RT). Primer extension reactions showed complete arrest of the 
      incorporation process using MMLV RT and AMV RT, while HIV RT preferentially 
      incorporates dAMP opposite epsilonA and dAMP as well as dTMP opposite epsilonC. The 
      properties of these RNA lesions are discussed in the context of its putative 
      biological role.
FAU - Calabretta, Alessandro
AU  - Calabretta A
AD  - Department of Chemistry and Biochemistry, University of Bern, Freiestrasse 3, 
      CH-3012 Bern, Switzerland.
FAU - Leumann, Christian J
AU  - Leumann CJ
LA  - eng
PT  - Journal Article
PT  - Research Support, Non-U.S. Gov't
DEP - 20130307
PL  - United States
TA  - Biochemistry
JT  - Biochemistry
JID - 0370623
RN  - 0 (3,N(4)-ethenocytosine)
RN  - 0 (Oligonucleotides)
RN  - 0 (Organophosphorus Compounds)
RN  - 0 (phosphoramidite)
RN  - 13875-63-3 (1,N(6)-ethenoadenine)
RN  - 63231-63-0 (RNA)
RN  - 8J337D1HZY (Cytosine)
RN  - JAC85A2161 (Adenine)
SB  - IM
MH  - Adenine/*analogs & derivatives/chemistry
MH  - *Base Pairing
MH  - Base Sequence
MH  - Circular Dichroism
MH  - Cytosine/*analogs & derivatives/chemistry
MH  - Nucleic Acid Denaturation
MH  - Oligonucleotides/*chemistry
MH  - Organophosphorus Compounds/chemistry
MH  - RNA/*chemistry
EDAT- 2013/02/22 06:00
MHDA- 2013/05/10 06:00
CRDT- 2013/02/22 06:00
PHST- 2013/02/22 06:00 [entrez]
PHST- 2013/02/22 06:00 [pubmed]
PHST- 2013/05/10 06:00 [medline]
AID - 10.1021/bi400116y [doi]
PST - ppublish
SO  - Biochemistry. 2013 Mar 19;52(11):1990-7. doi: 10.1021/bi400116y. Epub 2013 Mar 7.