Synthesis of polyamide nucleic acids (PNAs) using a novel Fmoc/Mmt protecting-group combination

Bioorganic and Medicinal Chemistry Letters

Volumn 6, Issue 6, 1996, Pages 665-670

  Breipohl, G ^a   Knolle, J ^a   Langner, D ^a   O'Malley, G ^a   Uhlmann, E ^a  

^a SANOFI   (France)

Author keywords

[No Author keywords available]

Indexed keywords

NUCLEIC ACID DERIVATIVE; POLYAMIDE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; REACTION ANALYSIS; TECHNIQUE;

EID: 0029871516     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/0960-894X(96)00082-0     Document Type: Article

References (12)

1. Egholm, M.; Nielsen, P.E.; Berg, R.H. and Buchardt, O.; Science 1991, 254, 1497-1500
2. Egholm, M.; Nielsen, P.E.; Berg, R.H. and Buchardt, O.; J. Am. Chem. Soc. 1992, 114, 1895-1897
3. for a review dephospho analogs see: Uhlmann, E.; Peyman, A.; Methods in Molecular Biology, Vol. 20: Protocols for Oligonucleotides and Analogs, Ed. Agrawal, S.; Humana Press Inc. 1993, pp 355-389
4. Dueholm, K.L.; Egholm, M.; Behrens, C.; Christensen, L.; Hansen, H.F.; Vulpius, T.; Petersen, K.H.; Berg, R.H.; Nielsen, P.E. and Buchardt, O.; J. Org. Chem. 1994, 59, 5767-5773
5. for a review see: Uhlmann, E. and Peyman, A.; Chem. Rev. 1990, 90, 543-584
6. Thomson S.A.; Josey, J. A.; Cadilla, R.; Gaul, M. D.; Hassman, C. F.; Luzzio, M. J.; Pipe, A. J.; Reed, K. L.; Ricca, D. J.; Wiethe, R. W.; Noble; S.A.; Tetrahedron 1995, 6179-6194
7. Will, D. W.; Breipohl, G.; Langner, D.; Knolle, J. and Uhlmann, E.; Tetrahedron 1995, 12069-12082
8. Heimer, E.P.; Gallo-Torres, H.E.; Felix, A.M.; Ahmad, M.; Lambros T.J.; Scheidl; F. and Meienhofer, J.; Int. J. Peptide Protein Res. 23, 1984, 203-211
9. Breipohl, G.; König, W.; EP 0460446, Hoechst AG
10. Coste, J.; Le-Nguyen, D. and Castro, B.; Tetrahedron Lett. 1990, 205-208
11. Breipohl, G.; Knolle, J. and Stüber, W.; Int. J. Peptide Protein Res., 1989, 34, 262-267
12. 6 + Na requires 826.2966)/ NMR: δ 10.50 (br s, 1H);7.9 - 6.8 (m, 24H); 4.50 (br s, 1.2H); 4.43 -4.15 (m, 3.8H); 3.90 and 3.78 (br s, 2H, two rotamers); 3.70 and 3.67 (s, 3H, two rotamers); 3.45 - 2.80 (m, 4H)}.