title: Synthesis and fluorescent properties of bi- and tricyclic 4-N-carbamoyldeoxycytidine derivatives.
abstract: 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.
authors.affiliation: 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.
authors.forename: Kenichi
authors.initials: K
authors.lastname: Miyata
authors.forename: Ryota
authors.initials: R
authors.lastname: Mineo
authors.forename: Ryuji
authors.initials: R
authors.lastname: Tamamushi
authors.forename: Masahiro
authors.initials: M
authors.lastname: Mizuta
authors.forename: Akihiro
authors.initials: A
authors.lastname: Ohkubo
authors.forename: Haruhiko
authors.initials: H
authors.lastname: Taguchi
authors.forename: Kohji
authors.initials: K
authors.lastname: Seio
authors.forename: Tomofumi
authors.initials: T
authors.lastname: Santa
authors.forename: Mitsuo
authors.initials: M
authors.lastname: Sekine
mesh_terms: D003841:Deoxycytidine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D013050:Spectrometry, Fluorescence
chemical_list: C515998:4-N-carbamoyldeoxycytidine; D003841:Deoxycytidine