J. Hovinen, SYNTHESIS OF CARBON-3-SUBSTITUTED 1,5,9-TRIAZACYCLODODECANES, RNA CLEAVAGE AGENTS SUITABLE FOR OLIGONUCLEOTIDE TETHERING, Bioconjugate chemistry, 9(1), 1998, pp. 132-136
Citations number
33
Categorie Soggetti
Chemistry Inorganic & Nuclear",Biology,"Biochemical Research Methods
Two derivatives of 1,5,9-triazacyclododecane bearing an alkylamino tet
her group at carbon-3 (7 and 13) were synthesized. The first of them,
7, was prepared starting from diethyl 2-(2-cyanoethyl)malonate and the
second one, 13, from glycerol. In both cases, the cyclization reactio
n was performed by allowing the corresponding ditosylates (5 and 12) t
o react with TBD. The guanidinium salts formed were reduced in situ to
the orthoamides (6 and 12), acid-catalyzed hydrolysis of which yielde
d the title compounds. The suitability of the azacrowns prepared for o
ligonucleotide tethering is also demonstrated.