[Oligodeoxynucleotides containing substituted 4-nitroindoles: synthesis and study of their DNA duplexes].
The synthesis of oligonucleotides containing 1-(2-deoxy-beta-D-ribofuranosyl)-2-methyl-4-nitroindole and 1-(2-deoxy-beta-D-ribofuranosyl)-2-phenyl-4-nitroindole is described. The synthesized modified oligonucleotides were used for studying the stability of intermolecular DNA duplexes with one unnatural strand and for evaluation of discriminating potential of 2-methyl- and 2-phenyl-4-nitroindoles toward nucleic bases. For comparison, an unmodified oligonucleotide and oligonucleotides bearing 5-nitroindole were used. It was shown that 2-methyl-4-nitroindole was only insignificantly inferior in stability to 5-nitroindole and characterized by a similar discriminating potential. 2-Phenyl-4-nitroindole provided a more pronounced duplex destabilization, the discrimination toward natural bases being decreased. The English version of the paper: Russian Journal of Bioorganic Chemistry, 2008, vol. 34, no. 2; see also http:// www.maik.ru.
Timofeev
E N
EN
Kolganova
N A
NA
Smirnov
I P
IP
Kochetkova
S V
SV
Florent'ev
V L
VL
D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry*; D009692:Nucleic Acid Heteroduplexes / Q000737:chemistry*; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis* / Q000737:chemistry; D013329:Structure-Activity Relationship; D013816:Thermodynamics; D044366:Transition Temperature
C530337:1-(2-deoxy-beta-D-ribofuranosyl)-2-methyl-4-nitroindole; C530338:1-(2-deoxy-beta-D-ribofuranosyl)-2-phenyl-4-nitroindole; D007211:Indoles; D009692:Nucleic Acid Heteroduplexes; D009838:Oligodeoxyribonucleotides