Nucleic-Acid Analogs with Constraint Conformational Flexibility in the Sugar-Phosphate Backbone 'Tricyclo-DNA' - Part 1: Preparation of [(5′ R,6′ R)-2′-Deoxy-3′,5′-ethano-5′,6′-methano-β-D- ribofuranosyl]thymine and -adenine, and the Corresponding Phosphoramidites for Oligonucleotide Synthesis

Helvetica Chimica Acta

Volumn 80, Issue 8, 1997, Pages 2426-2439

  Steffens, Ralph ^a   Leumann, Christian ^a  

^a UNIVERSITY OF BERN   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

(2' DEOXY 3',5' ETHANO 5',6' METHANO BETA RIBOFURANOSYL)ADENINE; (2' DEOXY 3',5' ETHANO 5',6' METHANO BETA RIBOFURANOSYL)THYMINE; 1 [5' O [BIS(4 METHOXYPHENYL)PHENYLMETHYL] 2' DEOXY 3',5' ETHANO 5',6' METHANO BETA RIBOFURANOSYL]THYMINE 3' (2 CYANOETHYL DIISOPROPYLPHOSPHORAMIDITE); CYCLIC NUCLEOTIDE; CYCLOPROPANE; DNA; N6 BENZOYL 9 [5' O [BIS(4 METHOXYPHENYL)PHENYLMETHYL] 2' DEOXY 3',5' ETHANO 5',6' METHANO BETA RIBOFURANOSYL]ADENINE 3' (2 CYANOETHYL DIISOPROPYLPHOSPHORAMIDITE); NUCLEIC ACID; OLIGONUCLEOTIDE; PHOSPHORAMIDIC ACID DERIVATIVE; SUGAR PHOSPHATE; UNCLASSIFIED DRUG;

ARTICLE; DRUG CONFORMATION; DRUG SYNTHESIS; NUCLEAR OVERHAUSER EFFECT; NUCLEIC ACID STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0031472758     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/hlca.19970800812     Document Type: Article

References (24)

1. U. Englisch, D. H. Gauss, Angew. Chem. 1991, 103, 629; ibid., Int. Ed. Engl. 1991, 30, 613; E. Uhlmann, A. Peyman, Chem. Rev. 1990, 90, 543; J. F. Milligan, M. D. Matteucci, J. C. Martin, J. Med. Chem. 1993, 36, 1923; A. De Mesmaeker, R. Häner, P. Martin, H. E. Moser, Acc. Chem. Res. 1995, 28, 366; K.-H. Altman, N. M. Dean, D. Fabbro, S. M. Freier, T. Geiger, R. Häner, D. Hüsken, P. Martin, B. P. Monia, M. Müller, F. Natt, P. Nidelin, J. Phillips, U. Pieles, H. Sasmor, H. E. Moser, Chimia 1996, 50, 168.
2. U. Englisch, D. H. Gauss, Angew. Chem. 1991, 103, 629; ibid., Int. Ed. Engl. 1991, 30, 613; E. Uhlmann, A. Peyman, Chem. Rev. 1990, 90, 543; J. F. Milligan, M. D. Matteucci, J. C. Martin, J. Med. Chem. 1993, 36, 1923; A. De Mesmaeker, R. Häner, P. Martin, H. E. Moser, Acc. Chem. Res. 1995, 28, 366; K.-H. Altman, N. M. Dean, D. Fabbro, S. M. Freier, T. Geiger, R. Häner, D. Hüsken, P. Martin, B. P. Monia, M. Müller, F. Natt, P. Nidelin, J. Phillips, U. Pieles, H. Sasmor, H. E. Moser, Chimia 1996, 50, 168.
3. U. Englisch, D. H. Gauss, Angew. Chem. 1991, 103, 629; ibid., Int. Ed. Engl. 1991, 30, 613; E. Uhlmann, A. Peyman, Chem. Rev. 1990, 90, 543; J. F. Milligan, M. D. Matteucci, J. C. Martin, J. Med. Chem. 1993, 36, 1923; A. De Mesmaeker, R. Häner, P. Martin, H. E. Moser, Acc. Chem. Res. 1995, 28, 366; K.-H. Altman, N. M. Dean, D. Fabbro, S. M. Freier, T. Geiger, R. Häner, D. Hüsken, P. Martin, B. P. Monia, M. Müller, F. Natt, P. Nidelin, J. Phillips, U. Pieles, H. Sasmor, H. E. Moser, Chimia 1996, 50, 168.
4. U. Englisch, D. H. Gauss, Angew. Chem. 1991, 103, 629; ibid., Int. Ed. Engl. 1991, 30, 613; E. Uhlmann, A. Peyman, Chem. Rev. 1990, 90, 543; J. F. Milligan, M. D. Matteucci, J. C. Martin, J. Med. Chem. 1993, 36, 1923; A. De Mesmaeker, R. Häner, P. Martin, H. E. Moser, Acc. Chem. Res. 1995, 28, 366; K.-H. Altman, N. M. Dean, D. Fabbro, S. M. Freier, T. Geiger, R. Häner, D. Hüsken, P. Martin, B. P. Monia, M. Müller, F. Natt, P. Nidelin, J. Phillips, U. Pieles, H. Sasmor, H. E. Moser, Chimia 1996, 50, 168.
5. U. Englisch, D. H. Gauss, Angew. Chem. 1991, 103, 629; ibid., Int. Ed. Engl. 1991, 30, 613; E. Uhlmann, A. Peyman, Chem. Rev. 1990, 90, 543; J. F. Milligan, M. D. Matteucci, J. C. Martin, J. Med. Chem. 1993, 36, 1923; A. De Mesmaeker, R. Häner, P. Martin, H. E. Moser, Acc. Chem. Res. 1995, 28, 366; K.-H. Altman, N. M. Dean, D. Fabbro, S. M. Freier, T. Geiger, R. Häner, D. Hüsken, P. Martin, B. P. Monia, M. Müller, F. Natt, P. Nidelin, J. Phillips, U. Pieles, H. Sasmor, H. E. Moser, Chimia 1996, 50, 168.
6. U. Englisch, D. H. Gauss, Angew. Chem. 1991, 103, 629; ibid., Int. Ed. Engl. 1991, 30, 613; E. Uhlmann, A. Peyman, Chem. Rev. 1990, 90, 543; J. F. Milligan, M. D. Matteucci, J. C. Martin, J. Med. Chem. 1993, 36, 1923; A. De Mesmaeker, R. Häner, P. Martin, H. E. Moser, Acc. Chem. Res. 1995, 28, 366; K.-H. Altman, N. M. Dean, D. Fabbro, S. M. Freier, T. Geiger, R. Häner, D. Hüsken, P. Martin, B. P. Monia, M. Müller, F. Natt, P. Nidelin, J. Phillips, U. Pieles, H. Sasmor, H. E. Moser, Chimia 1996, 50, 168.
7. B. Hyrup, P. E. Nielsen, Bioorg. Med. Chem. 1996, 4, 6.
8. C. M. Niemeyer, Angew. Chem. 1997, 109, 603.
9. C. A. Mirkin, R. L. Letsinger, R. C. Mucic, J. J. Storhoff, Nature (London) 1996, 382, 607.
10. A. P. Alivisatos, K. P. Johnsson, X. Peng, T. E. Wilson, C. J. Loweth, M. P. Bruchez Jr., P. G. Schultz, Nature (London) 1996, 382, 609.
11. M. Tarköy, M. Bolli, B. Schweizer, C. Leumann, Helv. Chim. Acta 1993, 76, 481.
12. M. Bolli, C. Litten, R. Schütz, C. Leumann, Chem. Biol. 1996, 3, 197.
13. P. Herdewijn, Liebigs Ann. 1996, 1337.
14. D. B. Dess, J. C. Martin, J. Org. Chem. 1983, 48, 4155; D. B. Dess, J. C. Martin, J. Am. Chem. Soc. 1991, 113, 7277.
15. D. B. Dess, J. C. Martin, J. Org. Chem. 1983, 48, 4155; D. B. Dess, J. C. Martin, J. Am. Chem. Soc. 1991, 113, 7277.
16. J. M. Conia, Pure Appl. Chem. 1975, 43, 317.
17. L. Friedman, J. G. Berger, J. Am. Chem. Soc. 1961, 83, 500.
18. J. A. Staroscik, B. Rickborn, J. Org. Chem. 1972, 37, 738.
19. H. Vorbrüggen, B. Bennua, Chem. Ber. 1981, 114, 1279.
20. R. Steffens, Dissertation Universität Bern, in preparation.
21. S. J. Weiner, P. A. Kollman, D. T. Nguyen, D. Case, J. Comput. Chem. 1986, 7, 230.
22. D. B. Davies, Prog. NMR Spectroc. 1978, 12, 135.
23. H. R. Drew, R. M. Wing, T. Takano, C. Broka, S. Tanaka, K. Itakura, R. E. Dickerson, Proc. Natl. Acad. Sci. U.S.A. 1981, 282, 743.
24. M. Tarköy, M. Bolli, C. Leumann, Helv. Chim. Acta 1994, 77, 716.