2′,2′-Ligation demonstrates the thermal dependence of DNA-directed positional control

Tetrahedron

Volumn 64, Issue 36, 2008, Pages 8417-8422

  Liu, Yu ^a   Sha, Ruojie ^a   Wang, Risheng ^a   Ding, Liang ^a   Canary, James W ^a   Seeman, Nadrian C ^a  

^a NEW YORK UNIVERSITY   (United States)

Author keywords

Nucleic acids; Positional synthesis; Reaction regioselectivity; Templated chemical ligation; Thermal control

Indexed keywords

AMINE; CARBOXYLIC ACID; NUCLEIC ACID; OLIGODEOXYNUCLEOTIDE; URIDINE DERIVATIVE;

ARTICLE; DNA TEMPLATE; GEL ELECTROPHORESIS; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; PRIORITY JOURNAL; TEMPERATURE SENSITIVITY;

EID: 47949091193     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.05.046     Document Type: Article

References (36)

1. Silverman A.P., and Kool E.T. Chem. Rev. 106 (2006) 3775-3789
2. Li X., and Liu D.R. Angew. Chem., Int. Ed. 43 (2004) 4848-4870
3. Summerer D., and Marx A. Angew. Chem., Int. Ed. 41 (2002) 89-90
4. Zhan Z.J., Ye J., Li X., and Lynn D.G. Curr. Org. Chem. 5 (2001) 885-902
5. Naylor R., and Gilham P.T. Biochemistry 5 (1966) 2722-2728
6. Inoue T., Joyce G.F., Grzeskowiak D., Orgel L.E., Brown J.M., and Reese C.B. J. Mol. Biol. 178 (1984) 669-676
7. Selvasekaran J., and Turnbull K.D. Bioorg. Med. Chem. 9 (2001) 2493-2500
8. Zhan Z.J., and Lynn D.G. J. Am. Chem. Soc. 119 (1997) 12420-12421
9. Luo P., Leitzel J.C., Zhan Z.J., and Lynn D.G. J. Am. Chem. Soc. 120 (1998) 3019-3031
10. Xu Y., Karalkar N.B., and Kool E.T. Nat. Biotechnol. 19 (2001) 148-152
11. Czlapinski J.L., and Sheppard T.L. J. Am. Chem. Soc. 123 (2001) 8618-8619
12. Ihara T., Fujiii T., Mukae M., Kitamura Y., and Jyo A. J. Am. Chem. Soc. 126 (2004) 8880-8881
13. Kumar R., EI-Sagheer A., Tumpane J., Lincoln P., Wilhelmsson L.M., and Brown T. J. Am. Chem. Soc. 129 (2007) 6859-6864
14. Fujimoto K., Matsuda S., Takahashi N., and Saito I. J. Am. Chem. Soc. 122 (2000) 5646-5647
15. Hong I.S., and Greenberg M.M. J. Am. Chem. Soc. 127 (2005) 3692-3693
16. Sawai H., Totsuka S., Yamamoto K., and Ozaki H. Nucleic Acids Res. 26 (1998) 2995-3000
17. Sawai H., Wada M., Kouda T., and Ozaki A.N. Chembiochem 7 (2006) 605-611
18. Wu X., Delgado G., Krishnamurthy R., and Eschenmoser A. Org. Lett. 4 (2002) 1283-1286
19. Zhu L., Lukeman P.S., Canary J.W., and Seeman N.C. J. Am. Chem. Soc. 125 (2003) 10178-10179
20. Zhu L., dos Santos O., Seeman N.C., and Canary J.W. Nucleosides Nucleotides and Nucleic Acids 21 (2002) 723-735
21. Ficht S., Mattes A., and Seitz O. J. Am. Chem. Soc. 126 (2004) 9970-9981
22. Dose C., Ficht S., and Seitz O. Angew. Chem., Int. Ed. 45 (2006) 5369-5373
23. Gartner Z.J., Kanan M.W., and Liu D.R. Angew. Chem., Int. Ed. 41 (2002) 1796-1800
24. Liu, Y.; Wang, R.; Ding, L.; Sha, R.; Lukeman, P. S.; Canary, J. W.; Seeman, N. C. Chembiochem, in press.
25. The LC-MS eluent contains 0.1% formic acid (C18 column); the nucleoside elution order is dC, dA, dG, and dT, which was confirmed by mass data and also by control experiments with commercial nucleosides and digests of unmodified DNA.
26. Werner D., Brunar H., and Noe C.R. Pharm. Acta Helv. 73 (1998) 3-10
27. Urban E., and Noe C.R. Il Farmaco 58 (2003) 243-258
28. Uesugi S., Miki H., Ikehara M., Iwahashi H., and Kyogoku Y. Tetrahedron Lett. 42 (1979) 4073-4076
29. Guschlbauer W., and Janlowski K. Nucleic Acids Res. 8 (1980) 1421-1433
30. Venkateswarlu D., Lind K.E., Mohan V., Manoharan M., and Ferguson D.M. Nucleic Acids Res. 27 (1999) 2189-2195
31. Ozaki H., Sato Y., Azuma S., and Sawai H. Nucleosides Nucleotides Nucleic acids 19 (2000) 593-601
32. Blackburn G.M., Gait M.J., Loakes D., and Williams D.M. Nucleic Acids in Chemistry and Biology Vol. 3 (2006), The Royal Society of Chemistry, Cambridge pp 64-67
33. Heller D., and Buschmann H. Top. Catal. 5 (1998) 159-176
34. Teranishi K., and Ueno F. Tetrahedron Lett. 43 (2002) 2393-2397
35. Gartner Z.J., and Liu D.R. J. Am. Chem. Soc. 123 (2001) 6961-6963
36. Gartner Z.J., Kanan M.W., and Liu D.R. J. Am. Chem. Soc. 124 (2002) 10304-10306