Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 25, Issue 58, Pages 13309-13317Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201902411
Keywords
RNA structures; oligoribonucleotides; postsynthetic modifications; tRNA; nucleosides
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Funding
- National Science Center, Poland [UMO-2017/25/B/ST5/00971]
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The synthesis of the protected form of 2-methylthio-N-6-threonylcarbamoyl adenosine (ms(2)t(6)A) was developed starting from adenosine or guanosine by using the optimized carbamate method and, for the first time, an isocyanate route. The hypermodified nucleoside was subsequently transformed into the protected ms(2)t(6)A-phosphoramidite monomer and used in a large-scale synthesis of the precursor 17nt ms(2)t(6)A-oligonucleotide (the anticodon stem and loop fragment of tRNA(Lys) from T. brucei). Finally, stereochemically secure ms(2)t(6)A -> ms(2)ct(6)A cyclization at the oligonucleotide level efficiently afforded a tRNA fragment bearing the ms(2)ct(6)A unit. The applied post-synthetic approach provides two sequentially homologous ms(2)t(6)A- and ms(2)ct(6)A-oligonucleotides that are suitable for further comparative structure-activity relationship studies.
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