Pyrrolidinyl peptide nucleic acid homologues: Effect of ring size on hybridization properties

Organic Letters

Volumn 14, Issue 6, 2012, Pages 1440-1443

  Mansawat, Woraluk ^a   Vilaivan, Chotima ^a   Balázs, Árpád ^b   Aitken, David J ^b   Vilaivan, Tirayut ^a  

^a CHULALONGKORN UNIVERSITY   (Thailand)

^b UNIVERSITÉ PARIS SUD   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOBUTANE DERIVATIVE; DNA; PEPTIDE NUCLEIC ACID; RNA;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; NUCLEIC ACID HYBRIDIZATION; NUCLEOTIDE SEQUENCE; SYNTHESIS;

BASE SEQUENCE; CYCLOBUTANES; DNA; MOLECULAR STRUCTURE; NUCLEIC ACID HYBRIDIZATION; PEPTIDE NUCLEIC ACIDS; RNA;

EID: 84858631870     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol300190u     Document Type: Article

References (40)

1. Silverman, S. K. Angew. Chem., Int. Ed. 2010, 49, 7180-7201
2. Aldaye, F. A.; Palmer, A. L.; Sleiman, H. F. Science 2008, 321, 1795-1799
3. Seeman, N. C. Mol. Biotechnol. 2007, 37, 246-257
4. Leumann, C. J. Bioorg. Med. Chem. 2002, 10, 841-854
5. Nielsen, P. E. Chem. Biodiversity 2010, 7, 796-804
6. Lundin, K. E.; Good, L.; Strömberg, R.; Gräslund, A.; Smith, C. I. E. Adv. Genet. 2006, 56, 1-51
7. Egholm, M.; Buchardt, O.; Christensen, L.; Behrens, C.; Freier, S. M.; Driver, D. A.; Berg, R. H.; Kim, S. K.; Norden, B.; Nielsen, P. E. Nature 1993, 365, 566-568
8. Corradini, R.; Sforza, S.; Tedeschi, T.; Totsingan, F.; Manicardi, A.; Marchelli, R. Curr. Top. Med. Chem. 2011, 11, 1535-1554
9. Efimov, V. A.; Aralov, A. V.; Chakhmakhcheva, O. G. Russ. J. Bioorg. Chem. 2010, 36, 663-683
10. Kumar, V. A.; Ganesh, K. N. Acc. Chem. Res. 2005, 38, 404-412
11. Pokorski, J. K.; Witschi, M. A.; Purnell, B. L.; Appella, D. H. J. Am. Chem. Soc. 2004, 126, 15067-15073
12. Govindaraju, T.; Kumar, V. A.; Ganesh, K. N. J. Am. Chem. Soc. 2005, 127, 4144-4145
13. Dragulescu-Andrasi, A.; Rapireddy, S.; Frezza, B. M.; Gayathri, C.; Gil, R. G.; Ly, D. H. J. Am. Chem. Soc. 2006, 128, 10258-10267
14. Englund, E. A.; Appella, D. H. Angew. Chem., Int. Ed. 2007, 46, 1414-1418
15. Manicardi, A.; Calabretta, A.; Bencivenni, M.; Tedeschi, T.; Sforza, S.; Corradini, R.; Marchelli, R. Chirality 2010, 22, E161-E172
16. Appella, D. H.; Christianson, L. A.; Klein, D. A.; Powell, D. R.; Huang, X.; Barchi, J. J., Jr.; Gellman, S. H. Nature 1997, 387, 381-382
17. Cheng, R. P.; Gellman, S. H.; DeGrado, W. F. Chem. Rev. 2001, 101, 3219-3232
18. Vasudev, P. G.; Chatterjee, S.; Shamala, N.; Balaram, P. Chem. Rev. 2011, 111, 657-687
19. Fülöp, F.; Martinek, T. A.; Tóth, G. K. Chem. Soc. Rev. 2006, 35, 323-334
20. Vilaivan, T.; Lowe, G. J. Am. Chem. Soc. 2002, 124, 9326-9327
21. Vilaivan, T.; Srisuwannaket, C. Org. Lett. 2006, 8, 1897-1900
22. Vilaivan, C.; Srisuwannaket, C.; Ananthanawat, C.; Suparpprom, C.; Kawakami, J.; Yamaguchi, Y.; Tanaka, Y.; Vilaivan, T. Artif. DNA: PNA XNA 2011, 2, 50-59
23. Ananthanawat, C.; Vilaivan, T.; Hoven, V. P.; Su, X. Biosens. Bioelectron. 2010, 25, 1064-1069
24. Vilaivan, T.; Suparpprom, C.; Harnyuttanakorn, P.; Lowe, G. Tetrahedron Lett. 2001, 42, 5533-5536
25. Vilaivan, T.; Suparpprom, C.; Duanglaor, P.; Harnyuttanakorn, P.; Lowe, G. Tetrahedron Lett. 2003, 44, 1663-1666
26. Ngamwiriyawong, P.; Vilaivan, T. Nucleosides, Nucleotides Nucleic Acids 2011, 30, 97-112
27. Fernandes, C.; Pereira, E.; Faure, S.; Aitken, D. J. J. Org. Chem. 2009, 74, 3217-3220
28. Declerck, V.; Aitken, D. J. Amino Acids 2011, 41, 587-595
29. Schinnerl, M.; Murray, J. K.; Langenhan, J. M.; Gellman, S. H. Eur. J. Org. Chem. 2003, 721-726
30. Xu, D.; Prasad, K.; Repič, O.; Blacklock, T. J. Tetrahedron: Asymmetry 1997, 8, 1445-1451
31. Lowe, G.; Vilaivan, T. J. Chem. Soc., Perkin Trans. 1 1997, 555-560
32. Taechalertpaisarn, J.; Sriwarom, P.; Boonlua, C.; Yotapan, N.; Vilaivan, C.; Vilaivan, T. Tetrahedron Lett. 2010, 51, 5822-5826
33. Aitken, D. J.; Gauzy, C.; Pereira, E. Tetrahedron Lett. 2004, 45, 2359-2361
34. Kim, S. K.; Nielsen, P. E.; Egholm, M.; Buchardt, O.; Berg, R. H.; Nordén, B. J. Am. Chem. Soc. 1993, 115, 6477-6481
35. Lohse, J.; Dahl, O.; Nielsen, P. E. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 11804-11808
36. Choi, S. H.; Guzei, I. A.; Spencer, L. C.; Gellman, S. H. J. Am. Chem. Soc. 2008, 130, 6544-6550
37. Siriwong, K.; Chuichay, P.; Saen-oon, S.; Suparpprom, C.; Vilaivan, T.; Hannongbua, S. Biochem. Biophys. Res. Commun. 2008, 372, 765-771
38. Appella, D. H.; Christianson, L. A.; Klein, D. A.; Richards, M. R.; Powell, D. R.; Gellman, S. H. J. Am. Chem. Soc. 1999, 121, 7574-7581
39. Fernandes, C.; Faure, S.; Pereira, E.; Théry, V.; Declerck, V.; Guillot, R.; Aitken, D. J. Org. Lett. 2010, 12, 3606-3609
40. Appella, D. H.; Christianson, L. A.; Karle, I. L.; Powell, D. R.; Gellman, S. H. J. Am. Chem. Soc. 1999, 121, 6206-6212