Translation of DNA into synthetic N-acyloxazolidines.
The translation of DNA into synthetic molecules enables their manipulation by powerful evolution-based methods previously available only to proteins and nucleic acids. The development of increasingly sophisticated DNA-templated small-molecule syntheses is crucial to broadening the scope of this approach. Here, we report the translation of DNA templates into monocyclic and bicyclic N-acyloxazolidines using multistep DNA-templated organic synthesis. Second-generation template architectures, used for the first time in a multistep DNA-templated synthesis, together with reactions and linker cleavage strategies not previously described in a DNA-templated format, were crucial to the successful translation. The products generated in this work represent the most complex small molecules to date synthesized in a DNA sequence-programmed manner and provide the basis for DNA-templated synthetic heterocycle libraries.
Li
Xiaoyu
X
Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts, 02138 USA.
Gartner
Zev J
ZJ
Tse
Brian N
BN
Liu
David R
DR
D000215:Acylation; D001360:Avidin / Q000737:chemistry; D001710:Biotin / Q000737:chemistry; D003500:Cyclization; D004247:DNA / Q000737:chemistry* / Q000235:genetics; D004591:Electrophoresis, Polyacrylamide Gel; D015394:Molecular Structure; D010080:Oxazoles / Q000138:chemical synthesis*; D014176:Protein Biosynthesis; D013698:Templates, Genetic
D010080:Oxazoles; C064210:oxazolidine; D001360:Avidin; D001710:Biotin; D004247:DNA