Synthesis and fluorescent properties of bi- and tricyclic 4-N-carbamoyldeoxycytidine derivatives.
New bi- and tricyclic deoxycytidine derivatives (dChpd, dCmpp, dCtpp, dCppp) were synthesized as analogues of a fluorescent nucleoside, dChpp, previously reported. The carbamoyl group of dChpd and the 5-position of the cytosine ring are bridged via an ethylene linker so that the modified group forms a nonplanar structure with the cytosine ring. The fluorescent study of dChpd indicated that the coplanar structure between the carbamoyl group and the cytosine ring is of importance. N-Methylation of the carbamoyl group (dCmpp) weakened the intensity of the fluorescence of dChpp, and the derivative (dCtpp), which had a thiocarbamoyl group, lost its fluorescent property. Moreover, addition of a pyrrolo-ring (dCppp) to dChpp enhanced the intensity of fluorescence, and an emission light was observed with a marked Stokes shift of 120 nm.
Miyata
Kenichi
K
Department of Life Science and Division of Collaborative Research for Bioscience and Biotechnology, Frontier Collaborative Research Center, Tokyo Institute of Technology, 4259 Nagatsuta, Midoriku, Yokohama 226-8501, Japan.
Mineo
Ryota
R
Tamamushi
Ryuji
R
Mizuta
Masahiro
M
Ohkubo
Akihiro
A
Taguchi
Haruhiko
H
Seio
Kohji
K
Santa
Tomofumi
T
Sekine
Mitsuo
M
D003841:Deoxycytidine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D013050:Spectrometry, Fluorescence
C515998:4-N-carbamoyldeoxycytidine; D003841:Deoxycytidine