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Issue 14, 2014
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A new modified cytosine base capable of base pairing with guanine using four hydrogen bonds

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Abstract

Oligonucleotides, containing 4-N-(1H-pyrrol-2-ylcarbonyl)deoxycytidine (dCPyc) and related derivatives, were synthesized via deprotection using 1.5 M NaOMe/MeOH. Among them, oligodeoxynucleotides containing dCPyc exhibited a higher hybridization affinity for DNA and RNA than the unmodified oligodeoxynucleotides. Comparative analysis between dCPyc and its derivatives by molecular dynamic simulation indicated that the CPyc residue could form four hydrogen bonds with the opposite G nucleobase keeping a more planar structure than the CInc residue where the Pyc group was replaced with a 1H-indol-2-ylcarbonyl group.

Graphical abstract: A new modified cytosine base capable of base pairing with guanine using four hydrogen bonds

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Publication details

The article was received on 04 Dec 2013, accepted on 10 Feb 2014 and first published on 11 Feb 2014


Article type: Paper
DOI: 10.1039/C3OB42420K
Author version available: Download Author version (PDF)
Citation: Org. Biomol. Chem., 2014,12, 2255-2262
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    A new modified cytosine base capable of base pairing with guanine using four hydrogen bonds

    K. Yamada, Y. Masaki, H. Tsunoda, A. Ohkubo, K. Seio and M. Sekine, Org. Biomol. Chem., 2014, 12, 2255
    DOI: 10.1039/C3OB42420K

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