(2S,5R/2R,5S)-Aminoethylpipecolyl aepip-aegPNA chimera: Synthesis and duplex/triplex stability

Tetrahedron

Volumn 60, Issue 42, 2004, Pages 9485-9491

  Shirude, Pravin S ^a   Kumar, Vaijayanti A ^a   Ganesh, Krishna N ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

aepipPNA; Peptide nucleic acids; Pipecolic acid PNA

Indexed keywords

1 (N TERT BUTYLOXYCARBONYLAMINOETHYL) 5 (N 3 BENZOYLTHYMIN 1 YL) 2 PIPECOLIC ACID METHYL ESTER; 1 (N TERT BUTYLOXYCARBONYLAMINOETHYL) 5 (THYMIN 1 YL) 2 PIPECOLIC ACID; 1 (N TERT BUTYLOXYCARBONYLAMINOETHYL) 5 (THYMIN 1 YL)PIPECOLIC ACID; 1 (N TERT BUTYLOXYCARBONYLAMINOETHYL) 5 HYDROXY 2 PIPECOLIC ACID METHYL ESTER; 5 HYDROXY N BENZYLOXYCARBONYL 2 PIPECOLIC ACID METHYL ESTER; COMPLEMENTARY DNA; DOUBLE STRANDED DNA; NUCLEIC ACID BASE; OLIGOMER; PEPTIDE NUCLEIC ACID; PIPERIDINE; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; AMINO ACID SUBSTITUTION; AMINO TERMINAL SEQUENCE; ARTICLE; CARBOXY TERMINAL SEQUENCE; CHIMERA; COMPLEX FORMATION; CONFORMATIONAL TRANSITION; DRUG STABILITY; DRUG SYNTHESIS; MOLECULAR RECOGNITION; OLIGOMERIZATION; PRIORITY JOURNAL; STEREOCHEMISTRY; TRANS ISOMER;

EID: 4544388216     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.07.080     Document Type: Article

References (29)

1. P.E. Nielsen Annu. Rev. Biophys. Biomol. Struct. 24 1995 167 183
2. K.N. Ganesh, and P.E. Nielsen Curr. Org. Chem. 4 2000 931 943
3. B. Hyrup, and P.E. Nielsen Bioorg. Med. Chem. Lett. 4 1996 5 23
4. L. Good, and P.E. Nielsen Antisense Nucleic Acids Drug Dev. 7 1997 431 437
5. M. Egholm, O. Buchardt, L. Christensen, C. Behrens, S.M. Freier, D.A. Driver, R.H. Berg, S.K. Kim, B. Norden, and P.E. Nielsen Nature 365 1993 566 568
6. E. Uhlmann, A. Peyman, G. Breipohl, and D.W. Will Angew. Chem., Int. Ed. 37 1998 2796 2823
7. J.C. Hanvey, N.J. Peffer, J.E. Bisi, S.A. Thomson, R. Cadilla, J.A. Josey, D.J. Ricca, F. Hassman, M.A. Bonham, K.G. Au, S.G. Carter, D.A. Bruckenstein, A.L. Boyd, S.A. Noble, and L.E. Babiss Science 258 1992 1481 1485
8. M. D'Costa, V.A. Kumar, and K.N. Ganesh Org. Lett. 1 1999 1513 1516
9. M. D'Costa, V.A. Kumar, and K.N. Ganesh Tetrahedron Lett. 43 2002 883 887
10. M. D'Costa, V.A. Kumar, and K.N. Ganesh Org. Lett. 3 2001 1281 1284
11. V.A. Kumar Eur. J. Org. Chem. 2002 2021 2032
12. T. Vilaivan, and G. Lowe J. Am. Chem. Soc. 124 2002 9326 9327
13. D.T. Hickman, P.M. King, M.A. Cooper, J.M. Slater, and J. Mickelfield Chem. Commun. 2000 2251 2252
14. A. Puschl, T. Boesen, G. Zuccarello, O. Dahl, S. Pitsch, and P.E. Nielsen J. Org. Chem. 66 2001 707 712
15. A. Eschenmoser, and M. Dobler Helv. Chim. Acta 75 1992 218 259
16. E. Lescrinier, R. Esnouf, J. Schraml, R. Busson, H.A. Heus, C.W. Hilbers, and P. Herdewijn Chem. Biol. 7 2000 719 731
17. P.S. Lonkar, and V.A. Kumar Bioorg. Med. Chem. Lett. 14 2004 2147 2149
18. A. Püschl, T. Boesen, T. Tedeschi, O. Dahl, and P.E. Nielsen J. Chem. Soc., Perkin Trans. 1 21 2001 2757 2763
19. P.S. Shirude, V.A. Kumar, and K.N. Ganesh Tetrahedron Lett. 45 2004 3085 3088
20. P.D. Bailey, and J.S. Bryans Tetrahedron Lett. 29 1988 2231 2234
21. D.R. Adams, P.D. Bailey, J.H. Heffernan, and S. Stokes Chem. Commun. 1996 349 350
22. G.B. Fields, and C.G. Fields J. Am. Chem. Soc. 113 1991 4202 4207
23. calcd=2189.10)
24. M.J. Gait Oligonucleotide Synthesis, A Practical Approach 1984 IRL Oxford
25. S.H. Kim, P.E. Nielsen, M. Egholm, and O. Buchardt J. Am. Chem. Soc. 115 1993 6477 6489
26. Perrin, D.D.; Amarego, W. L. F. In Purification of Laboratory Chemicals. 3rd ed.; Pergamon: Oxford, 1989.
27. D.A. Barawkar, K.G. Rajeev, V.A. Kumar, and K.N. Ganesh Nucleic Acids Res. 24 1996 1229 1237
28. P.C. Meltzer, A.Y. Liang, and P. Matsudaira J. Org. Chem. 60 1995 4305 4308
29. E. Kaiser, R.L. Colescott, C.D. Bossinger, and P.I. Cook Anal. Biochem. 34 1970 595 598