Structure of puromycin aminonucleoside

Abstract

3'-Amino-3'-deoxy-N,N-dimethyladenosine, $C_{12}H_{18}N_6O_3$, $M_r = 294.3$, monoclinic, $P2_1$, a = 4.684(1), b= 10.252(1), c= 14.381 (3)\AA, \beta = 91.16 (2)°, V= 690.49 $\AA^3$, Z = 2, $D_x = 1.39$ Mg $m^{-3}$, \lambda(Cu K\alpha) = 1.5418 \AA, \mu = 0.84 $mm^{-1}$, F(000) = 312, T= 295 K, R =0.045 for 986 observed reflections with I > 1.5\sigma(I). The adenine base is unprotonated at N(I) and is dimethylated at N(6). The nucleoside has a 3'-deoxy-3'-aminofuranosyl ribose sugar. The base is in the anti conformation (x= 2.3°) with respect to the furanosyl ring, which shows a C(3')-endo-C(2')-exo pucker $(_2T^3)$. 0(5') is disordered. The structure of the compound is similar to that of the nucleoside portion of the antibiotic puromycin.