Journal of the American Chemical Society
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synthesize by the Yoshikawa or Ludwig-Eckstein methods16,17
.
Based on these considerations, we believe that the current ap-
proach provides an alternative paradigm for synthesizing large
quantities of nucleoside triphosphates for emerging applications
in biotechnology and molecular medicine.
(10)
Wang, Y.; Ngor, A. K.; Nikoomanzar, A.;
Chaput, J. C. Evolution of a General RNA-Cleaving FANA Enzyme.
Nat. Commun. 2018, 9, 5067.
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Rangel, A. E.; Chen, Z.; Ayele, T. M.; Heemstra,
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Burgess, K.; Cook, D. Syntheses of Nucleoside
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Triphosphates. Chem. Rev. 2000, 100, 2047-2060.
ASSOCIATED CONTENT
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Kore, A. R.; Srinivasan, B. Recent Advances in
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the Synthesis of Nucleoside Triphosphates. Curr. Org. Syn. 2013,
10, 903-934.
Supporting Information.
Additional information and experimental methods. This material
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Hollenstein, M. Nucleoside triphosphates--
building blocks for the modification of nucleic acids. Molecules 2012,
17, 13569-91.
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AUTHOR INFORMATION
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Roy, B.; Depaix, A.; Perigaud, C.; Peyrottes, S.
Recent Trends in Nucleotide Synthesis. Chem Rev 2016, 116, 7854-
97.
Corresponding Author
*jchaput@uci.edu
(16)
Yoshikawa, M.; Kato, T.; Takenishi, T. A novel
method for phosphorylation of nucleosides to 5'-nucleotides.
Tetrahedron Lett. 1967, 8, 5065-5068.
Notes
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Ludwig, J.; Eckstein, F. Rapid and efficient
J.L., S.B., and J.C. are named inventors on a provisional pa-
tent application describing the synthesis and application or-
ganic pyrophosphate reagents.
synthesis of nucleoside 5'-0 -( 1-thiotriphosphates), 5'-triphosphates
and 2',3'-cyclophosphorothioates using 2-chloro-4H- 1,3,2-
benzodioxaphosphorin-4-one. J. Org. Chem. 1989, 54, 631-635.
(18)
Hofer, A.; Cremosnik, G. S.; Muller, A. C.;
Giambruno, R.; Trefzer, C.; Superti-Furga, G.; Bennett, K. L.;
Jessen, H. J. A Modular Synthesis of Modified Phosphoanhydrides.
Chemistry 2015, 21, 10116-22.
ACKNOWLEDGMENT
We would like to thank members of the Chaput laboratory for
helpful discussions and critical reading of the manuscript. This
work was supported by the DARPA Folded Non-Natural Poly-
mers with Biological Function Fold F(x) Program under award
number N66001-16-2-4061.
(19)
synthesis
phosphoramidites. Angew. Chem. Int. Ed. Engl. 2014, 53, 286-9.
(20) Sau, S. P.; Chaput, J. C. A Gram-Scale HPLC-
Cremosnik, G. S.; Hofer, A.; Jessen, H. J.
Iterative
of nucleoside oligophosphates with
Free Synthesis of TNA Triphosphates Using an Iterative
Phosphorylation Strategy. Org. Lett. 2017, 19, 4379-4382.
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Hoard, D. E.; Ott, D. G. Conversion of Mono-
and Oligodeoxyribonucleotides to 5-Triphosphates. J. Am. Chem.
Soc. 1965, 87, 1785-8.
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