Issue 14, 2014

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

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

Supplementary files

Article information

Article type
Paper
Submitted
04 Dec 2013
Accepted
10 Feb 2014
First published
11 Feb 2014

Org. Biomol. Chem., 2014,12, 2255-2262

Author version available

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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