Synthesis and properties of a new fluorescent bicyclic 4-N-carbamoyldeoxycytidine derivative.
[reaction: see text] A bicyclic 4-N-carbamoyldeoxycytidine derivative (1, dC(hpp)) geometrically locked was synthesized as a new fluorescent nucleobase. The hybridization properties of oligodeoxynucleotides containing dC(hpp) were investigated by use of T(m) analysis. It was found that dC(hpp) forms stable base pairs not only with the complementary guanine base, but also with the adenine base. Interestingly, the fluorescence of dC(hpp) was suppressed only when a dC(hpp)-dG base pair was formed.
Miyata
Kenichi
K
Department of Life Science, Tokyo Institute of Technology, 4259 Nagatsuta, Midoriku, Yokohama 226-8501, Japan.
Tamamushi
Ryuji
R
Ohkubo
Akihiro
A
Taguchi
Haruhiko
H
Seio
Kohji
K
Santa
Tomofumi
T
Sekine
Mitsuo
M
D020029:Base Pairing; D004247:DNA / Q000737:chemistry*; D003841:Deoxycytidine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000737:chemistry*; D006147:Guanine / Q000737:chemistry; D015394:Molecular Structure; D012689:Sequence Homology, Nucleic Acid; D013329:Structure-Activity Relationship
C515998:4-N-carbamoyldeoxycytidine; D005456:Fluorescent Dyes; D003841:Deoxycytidine; D006147:Guanine; D004247:DNA