Synthesis of Guanosines and Deoxyguanosines from 5-amino-1-(β-D-ribofuranosyl)imidazole-4-carboxamide ('AICA-riboside')
Methods are described for the synthesis of 15N-labelled guanosines and deoxyguanosines, suitable for incorporation into oligonucleotides.The 15N is located at N-1 (e.g. guanosine 1a and deoxyguanosine 1b> or at the NH2 (e.g. guanosine 1
Bleasdale, Christine,Ellwood, Simon B.,Golding, Bernard T.,Slaich, Pritpal K.,Taylor, Oonah J.,Watson, William P.
p. 2859 - 2866
(2007/10/02)
A NOVEL AND EFFICIENT SYNTHESIS OF ISOGUANOSINE
Isoguanosine (4b) was synthesized by a one-pot reaction involving a condensation of 5-amino-1-(β-D-ribofuranosyl)imidazole-4-carboxamide (1b) with benzoyl isothiocyanate, treatment of the resulting thiourea derivative with DCC furnished 5-(N1-benzoylcarbamoyl)aminoimidazole-4-carbonitrile (3b) which was then annulated with ethanolic ammonia to afford isoguanosine in a 68percent yield from 1b.
5-Amino-1β-D-ribofuranosylimidazole-4-carboxamide ('AICA-riboside', 2) has been converted into guanosine ; the mechanism of formation of the pyrimidine ring in the nucleoside has been elucidated.
Golding, Bernard T.,Slaich, Pritpal K.,Watson, William P.
p. 901 - 902
(2007/10/02)
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