Kg. Rajeev et al., CONFORMATIONALLY RESTRAINED CHIRAL ANALOGS OF SPERMINE - CHEMICAL SYNTHESIS AND IMPROVEMENTS IN DNA TRIPLEX STABILITY, Journal of organic chemistry, 62(15), 1997, pp. 5169-5173
The synthesis of novel chiral analogues of spermine, 11 (2R,4S) and 14
(2S,4R), is reported starting from trans-4-hydroxy-L-proline 3. These
cyclic analogues are generated from linear, achiral spermine by incor
porating a pyrrolidine ring on the backbone to effect conformational r
igidity, with simultaneous creation of two asymmetric centers. The chi
ral analogues bind both AT and CG rich DNA duplexes as effectively as
spermine and exhibit even better association with DNA tripler than spe
rmine. The newer analogues have features for structural elaboration to
novel molecular entities of potential importance in therapeutics and
material design.