A New Efficient Synthesis of Long‐Chain Di‐ and Triaminopolyols

Abstract

The asymmetric synthesis of long‐chain di‐ and triaminopolyols is reported. The developed methodology is based on the functionalization of 3,3′‐methylenebis{[6‐(benzyloxy)methoxy]cyclohept‐3‐en‐1‐ol} derivatives that allows theselective introduction of amine moieties at defined positions of polyketide fragments. The versatile strategy disclosed here requires few purification steps and may generate a large panel of stereoisomers. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

Synthesis and Biological Evaluation of Modified 2-Deoxystreptamine Dimers

“…8 Here, we report on the preparation and RNA affinity evaluation of 2-DOS dimers as well as polyamine and aminopolyketide linked analogues. 9,10 Enhancement of the RNA binding affinities for dimeric aminoglycosides may result from an increased overall positive charge and from the possibility to target multiple binding sites within large RNA molecules. In particular, long and conformationally flexible spacers should allow the resulting conjugates to search for several binding sites by screening variable conformations.…”

“…In summary, we have synthesized 2-deoxystreptamine dimers linked by naturally occurring polyamines or aminofunctionalized polyketides. 9 Some analogues containing substituted furyl moieties have been prepared from furyl amino acid building blocks. Evaluation of the bind- ing of rRNA mimics to these derivatives revealed high affinity of the flexible polyketide (+)-16.…”