The Journal of Organic Chemistry
Note
(22) Kehler, J.; Puschl, A.; Dahl, O. Nucleosides Nucleotides 1997, 16,
1633−1636.
ASSOCIATED CONTENT
* Supporting Information
■
S
(23) Yau, E. K.; Ma, Y.-X.; Caruthers, M. H. Tetrahedron Lett. 1990,
31, 1953−1956.
1H NMR, 13C NMR and 31P NMR spectra of phosphor-
othioamidites 2a−2d; HRMS spectra of new phosphorothioa-
midites 2a−2c; MALDI-TOF mass spectra of oligonucleotides
3a−3f; HPLC profiles of the crude and purified oligonucleo-
tides (3a, 3c, 3e and 3f); trityl yields of 3e and 3f from the
solid-phase synthesis. This material is available free of charge
(24) Brill, W. K.-D.; Nielsen, J.; Caruthers, M. H. J. Am. Chem. Soc.
1991, 113, 3972−3980.
(25) Grandas, A.; Marshall, W. S.; Nielsen, J.; Caruthers, M. H.
Tetrahedron Lett. 1989, 30, 543−546.
(26) Nielsen, J.; Brill, W. K.-D.; Caruthers, M. H. Tetrahedron Lett.
1988, 29, 2911−2914.
(27) Brill, W. K.-D.; Nielsen, J.; Caruthers, M. H. Tetrahedron Lett.
1988, 29, 5517−5520.
AUTHOR INFORMATION
Corresponding Author
■
(28) Bjergarde, K.; Dahl, O. Nucleic Acids Res. 1991, 19, 5843−5850.
(29) Brill, W. K.-D.; Tang, J.-Y.; Ma, Y.-X.; Caruthers, M. H. J. Am.
Chem. Soc. 1989, 111, 2321−2322.
Present Address
(30) Wiesler, W. T.; Caruthers, M. H. J. Org. Chem. 1996, 61, 4272−
4281.
‡Department of Pathology and Laboratory Medicine, The
University of Rochester Medical Center, 601 Elmwood Avenue,
Box 626, Rochester, NY 14642.
(31) Greef, C. H.; Seeberger, P. H.; Caruthers, M. H. Tetrahedron
Lett. 1996, 37, 4451−4454.
(32) Petersen, K. H.; Nielsen, J. Tetrahedron Lett. 1990, 31, 911−914.
(33) Yang, X.; Sierant, M.; Janicka, M.; Peczek, L.; Martinez, C.;
Hassell, T.; Li, N.; Li, X.; Wang, T.; Nawrot, B. ACS Chem. Biol. 2012,
7, 1214−1220.
Notes
The authors declare no competing financial interest.
(34) Derrick, W. B.; Greef, C. H.; Caruthers, M. H.; Uhlenbeck, O.
C. Biochemistry 2000, 39, 4947−4954.
ACKNOWLEDGMENTS
■
Dedicated to the memory of Prof. Yao-Zeng Huang on his
100th birthday. This work was supported by an NIH grant to
J.A.P. (1R01AI081987). J.K.F. was also supported by the
University of Chicago Medical Scientist Training Program (5
T32 GM07281).
(35) Bergot, B. J.; Egan, W. J. Chromatogr. 1992, 599, 35−42.
(36) Iyer, R. P.; Egan, W.; Regan, J. B.; Beaucage, S. L. J. Am. Chem.
Soc. 1990, 112, 1253−1254.
(37) Frederiksen, J. K.; Li, N.-S.; Das, R.; Herschlag, D.; Piccirilli, J.
A. RNA 2012, 18, 1123−1141.
(38) An attempt to extend the scope of our approach to prepare 5′-
Ups2Ups2Ups2Ups2Ups2U-3′ containing exclusively phosphorodi-
thioate linkages was not successful. The yields dropped significantly
even though double coupling was used for each linkage. The reasons
are still unclear. Therefore, our method may not be suitable for
synthesizing oligonucleotides containing exclusively phosphorodi-
thioate linkages.
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