ja9b09937_si_001.pdf (17.96 MB)
Mercury-Free Automated Synthesis of Guanidinium Backbone Oligonucleotides
journal contribution
posted on 2019-12-16, 05:31 authored by Kacper Skakuj, Katherine E. Bujold, Chad A. MirkinA new method for synthesizing deoxynucleic guanidine
(DNG) oligonucleotides
that uses iodine as a mild and inexpensive coupling reagent is reported.
This method eliminates the need for the toxic mercury salts and pungent
thiophenol historically used in methods aimed at preparing DNG oligonucleotides.
This coupling strategy was readily translated to a standard MerMade
12 oligonucleotide synthesizer with coupling yields of 95% and has
enabled the synthesis of a 20-mer DNG oligonucleotide, the longest
DNG strand to date, in addition to mixed DNA–DNG sequences
with 3–9 DNG inserts. Importantly, DNG oligonucleotides exhibit
robust unaided cellular uptake as compared to unmodified oligonucleotides
without apparent cellular toxicity. Taken together, these findings
should greatly increase the accessibility of cationic backbone modifications
and assist in the development of oligonucleotide-based drugs.
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DNG oligonucleotides exhibitDNG oligonucleotidesMerMade 12 oligonucleotide synthesizer20- mer DNG oligonucleotidesynthesizing deoxynucleic guanidineMercury-Free Automated Synthesisoligonucleotide-based drugsGuanidinium Backbone OligonucleotidesmethodDNAmercury saltsDNG strandcationic backbone modifications
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