Highly efficient synthesis of DNA-binding hairpin polyamides via the use of a new triphosgene coupling strategy.
A facile and highly efficient solid phase synthesis method is reported for the preparation of hairpin DNA-binding polyamides using the cost-effective triphosgene (BTC) activating agent. Difficult polyamide sequences were prepared from N-methylimidazole (Im) and N-methylpyrrole (Py) building blocks with high stepwise yields (>98%) using Boc chemistry. The versatility of the triphosgene coupling approach was also demonstrated for the first time on aryl hydrazine resins to afford biomedically relevant tail-truncated polyamides in excellent isolated yields.
Su
Wu
W
Department of Chemistry, University of Leicester, University Road, Leicester, UK.
Gray
Stephen J
SJ
Dondi
Ruggero
R
Burley
Glenn A
GA
D004247:DNA / Q000737:chemistry / Q000378:metabolism*; D007093:Imidazoles / Q000737:chemistry; D015394:Molecular Structure; D009757:Nylons / Q000138:chemical synthesis* / Q000737:chemistry; D011758:Pyrroles / Q000737:chemistry
D007093:Imidazoles; D009757:Nylons; D011758:Pyrroles; D004247:DNA; C096654:N-methylpyrrole; C018100:1-methylimidazole