Microwave Assisted Synthesis of Py-Im Polyamides
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چکیده
منابع مشابه
Microwave Assisted Synthesis of Py-Im Polyamides
Microwave synthesis was utilized to rapidly build Py-Im polyamides in high yields and purity using Boc-protection chemistry on Kaiser oxime resin. A representative polyamide targeting the 5'-WGWWCW-3' (W = A or T) subset of the consensus Androgen and Glucocorticoid Response Elements was synthesized in 56% yield after 20 linear steps and HPLC purification. It was confirmed by Mosher amide deriva...
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Groove specificity. Pyrrole-imidazole polyamides are well-known for their specific interactions with the minor groove of DNA. Here we demonstrate that polyamides do not similarly bind duplex RNA, and offer a structural rationale for the molecular-level discrimination of nucleic acid duplexes by minor groove binding ligands.
متن کاملSynthesis of Cyclic Py-Im Polyamide Libraries
Cyclic Py-Im polyamides containing two GABA turn units exhibit enhanced DNA binding affinity, but extensive studies of their biological properties have been hindered due to synthetic inaccessibility. A facile modular approach toward cyclic polyamides has been developed via microwave-assisted solid-phase synthesis of hairpin amino acid oligomer intermediates followed by macrocyclization. A focus...
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Pyrrole-imidazole (Py-Im) hairpin polyamides are a class of programmable, sequence-specific DNA binding oligomers capable of disrupting protein-DNA interactions and modulating gene expression in living cells. Methods to control the cellular uptake and nuclear localization of these compounds are essential to their application as molecular probes or therapeutic agents. Here, we explore modificati...
متن کاملPharmacokinetics of Py-Im polyamides depend on architecture: cyclic versus linear.
The pharmacokinetic properties of three pyrrole-imidazole (Py-Im) polyamides of similar size and Py-Im content but different shape were studied in the mouse. Remarkably, hairpin and cyclic oligomers programmed for the same DNA sequence 5'-WGGWWW-3' displayed distinct pharmacokinetic properties. Furthermore, the hairpin 1 and cycle 2 exhibited vastly different animal toxicities. These data provi...
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ژورنال
عنوان ژورنال: Organic Letters
سال: 2012
ISSN: 1523-7060,1523-7052
DOI: 10.1021/ol3010003