Conversion of formycin into the fluorescent isoguanosine analogue 7-amino-3-(β-D-ribofuranosyl)-1H-pyrazolo[4,3-d]pyrimidin-5(4H)-one
- 1 January 1984
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 10,p. 2421-2423
- https://doi.org/10.1039/p19840002421
Abstract
On u.v. irradiation, in aqueous solution, formycin N(6)-oxide (3) undergoes photorearrangement to give 5-cyano-3-(β-D-ribofuranosyl)-4-ureido-1H-pyrazole (5) as the major product; small amounts of 7-amino-3-(β-D-ribofuranosyl)-1H-pyrazolo[4,3-d]pyrimidin-5(4H)-one (4) and formycin (1) are also formed. When treated with aqueous ammonia, compound (5) cyclizes to the isoguanosine analogue (4). The latter compound is strongly fluorescent and its c.d. spectrum resembles that of formycin. Its u.v. absorption and fluorescence characteristics are compared with those of the corresponding guanosine analogue 5-amino-3-(β-D-ribofuranosyl)-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one (2).This publication has 0 references indexed in Scilit: