- Formation of 2-chloroinosine from guanosine by treatment of HNO2 in the presence of NaCl
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We investigated the reaction of Guo with nitrous acid in the presence of NaCl. When 1 mM Guo was incubated with 100 mM NaNO2 and 2 M NaCl in sodium acetate buffer at pH 3.2 and 37°C, 2-chloroinosine (2-Cl-Ino) was produced in addition to oxanosine (Oxo) and xanthosine (Xao). The yield of 2-Cl-Ino was 0.033 mM at an incubation time of 2 h. Under the same reaction conditions, GMP and dGuo gave rise to the corresponding 2-chloro derivatives with comparable yields. All the 2-chloro derivatives were fairly stable (t1/2>360 h) at physiological pH and temperature. To elucidate the reaction mechanism of the chlorination, the diazoate derivative of Guo, a reaction intermediate of the Guo-HNO2 system, was employed as a starting compound. When the diazoate was incubated with 2 M NaCl in a neutral solution, 2-Cl-Ino was produced in addition to Oxo and Xao. These results suggest that the 2-chloro derivatives can be produced from foodstuffs in the human stomach and may have potential importance as a carcinogen causing gastric cancer.
- Suzuki, Toshinori,Ide, Hiroshi,Yamada, Masaki,Morii, Takashi,Makino, Keisuke
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p. 2937 - 2941
(2007/10/03)
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- A new synthesis of oxanosine and 2'-deoxyoxanosine
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An easy and more efficient synthesis of oxanosine and 2'-deoxyoxanosine has been developed, a key step in the reported synthesis is a new photochemical transformation by UV irradiation of 1-hydroxy derivatives of inosine.
- De Napoli, Lorenzo,Di Fabio, Giovanni,Messere, Anna,Montesarchio, Daniela,Piccialli, Gennaro,Varra, Michela
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p. 7397 - 7400
(2007/10/03)
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