Synthesis and incorporation into oligodeoxynucleotides of carbocyclic exo-amino nucleosides

Synthesis

Volumn 44, Issue 7, 2012, Pages 1011-1025

  Yaren, Oezlem ^a   Röthlisberger, Pascal ^a   Leumann, Christian J ^a  

^a UNIVERSITY OF BERN   (Switzerland)

Author keywords

medicinal chemistry; molecular recognition; nucleobases; nucleosides; oligonucleotides

Indexed keywords

BASE-PAIRING; BUILDING BLOCKES; DNA DUPLEXES; DNA SYNTHESISS; MEDICINAL CHEMISTRY; NATURAL BASIS; NUCLEOBASES; NUCLEOSIDE ANALOGUES; NUCLEOSIDES; OLIGODEOXYNUCLEOTIDES; OTHER APPLICATIONS; PAIRING PROPERTIES; PRIMARY AROMATIC AMINES; SPECIFIC INTERACTION; SYNTHETIC ROUTES;

MOLECULAR RECOGNITION; OLIGONUCLEOTIDES;

BIOMOLECULES;

1,3 PHENYLENEDIAMINE; 1,5 DIAMINONAPHTHALENE; 3 AMINOPYRIDINE; 6 AMINOFLAVONE; AMINONUCLEOSIDE; ANILINE; AROMATIC AMINE; CARBOCYCLIC NUCLEOSIDE; DNA; DOUBLE STRANDED DNA; FLAVONE DERIVATIVE; NAPHTHALENE DERIVATIVE; NUCLEOSIDE ANALOG; NUCLEOTIDE; OLIGODEOXYNUCLEOTIDE; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; BASE PAIRING; BIOTECHNOLOGY; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; DNA SYNTHESIS; EPIMER; MASS SPECTROMETRY; PROTEIN INTERACTION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 84859100985     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0031-1289737     Document Type: Article

References (33)

1. Daluge S M., Good S S., Faletto M B., Miller W H., StClair M H., Boone L R., Tisdale M, Parry N R., Reardon J E., Dornsife R E., Averett D R., Krenitsky T A., Antimicrob. Agents Chemother. 1997 41 1082
2. Helguera A M., Rodríguez-Borges J E., Caamaño O, García-Mera X, González M P., Cordeiro M N. D. S., Mol. Inf. 2010 29 213
3. Hergueta A R., Fernandez F, Lopez C, Balzarini J, De Clercq E, Chem. Pharm. Bull. 2001 49 1174
4. Crimmins M T., King B W., J. Org. Chem. 1996 61 4192
5. Sagi J, Szemzö A, Szécsi J, Ötvös L, Nucleic Acids Res. 1990 18 2133
6. Freier S M., Altmann K H., Nucleic Acids Res. 1997 25 4429
7. Altmann K H., B'Vierre M O., De Mesmaeker A, Moser H E., Bioorg. Med. Chem. Lett. 1995 5 431
8. Altmann K H., Kesselring R, Francotte E, Rihs G, Tetrahedron Lett. 1994 35 2331
9. Altmann K H., Kesselring R, Synlett 1994 853
10. Altmann K H., Imwinkelried R, Kesselring R, Rihs G, Tetrahedron Lett. 1994 35 7625
11. Marquez V E., Siddiqui M A., Ezzitouni A, Russ P, Wang J, Wagner R W., Matteucci M D., J. Med. Chem. 1996 39 3739
12. Saneyoshi H, Mazzini S, Aviñó A, Portella G, González C, Orozco M, Marquez V E., Eritja R, Nucleic Acids Res. 2009 37 5589
13. Kubo I, Kim M, Wood W F., Naoki H, Tetrahedron Lett. 1986 27 4277
14. Moss R J., Petrie C R., Meyer R B., Nord L D., Willis R C., Smith R A., Larson S B., Kini G D., Robins R K., J. Med. Chem. 1988 31 786
15. Fortin H, Tomasi S, Delcros J.-G, Bansard J.-Y, Boustie J, ChemMedChem 2006 1 189
16. Varaprasad C V., Habib Q, Li D Y., Huang J F., Abt J W., Rong F, Hong Z, An H Y., Tetrahedron 2003 59 2297
17. Greenberg M M., Acc. Chem. Res. 2012 45 DOI: 10.1021/ar2002182
18. Agrofoglio L, Condom R, Guedj R, Challand S R., Selway J, Nucleosides Nucleotides 1994 13 1147
19. Agrofoglio L, Condom R, Guedj R, Challand R, Selway J, Tetrahedron Lett. 1993 34 6271
20. Wojciechowski F, Leumann C J., Chem. Soc. Rev. 2011 40 5669
21. Seo Y J., Malyshev D A., Lavergne T, Ordoukhanian P, Romesberg F E., J. Am. Chem. Soc. 2011 133 19878
22. Seo Y J., Hwang G T., Ordoukhanian P, Romesberg F E., J. Am. Chem. Soc. 2009 131 3246
23. Kool E T., Sintim H O., Chem. Commun. 2006 3665
24. Hirao I, Kimoto M, Mitsui T, Fujiwara T, Kawai R, Sato A, Harada Y, Yokoyama S, Nat. Meth. 2006 3 729
25. Yaren O, Mosimann M, Leumann C J., Angew. Chem. Int. Ed. 2011 50 1935
26. Biggadike K, Borthwick A D., Evans D, Exall A M., Kirk B E., Roberts S M., Stephenson L, Youds P, J. Chem. Soc., Perkin Trans. 1 1988 549
27. Ludek O R., Meier C, Synthesis 2003 2101
28. Huang H, Greenberg M M., J. Org. Chem. 2008 73 2695
29. Oligonucleotides and Analogues - A Practical Approach Oxford University Press Oxford 1991
30. Brotschi C, Mathis G, Leumann C J., Chem. Eur. J. 2005 11 1911
31. Grigorenko N A., Leumann C J., Chem. Eur. J. 2009 15 639
32. Matsuda S, Fillo J D., Henry A A., Rai P, Wilkens S J., Dwyer T J., Geierstanger B H., Wemmer D E., Schultz P G., Spraggon G, Romesberg F E., J. Am. Chem. Soc. 2007 129 10466
33. Hildbrand S, Blaser A, Parel S P., Leumann C J., J. Am. Chem. Soc. 1997 119 5499