Side chain homologation of alanyl peptide nucleic acids: Pairing selectivity and stacking

Organic and Biomolecular Chemistry

Volumn 3, Issue 6, 2005, Pages 1058-1066

  Diederichsen, Ulf ^a   Weicherding, Daniel ^a,b   Diezemann, Nicola ^a  

^a Institute of Organic Chemistry   (Germany)

^b Clondiag Chip Technologies GmbH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; AMINO ACIDS; ESTERS; ETHYLENE; ISOMERS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUCLEIC ACIDS; POLYPEPTIDES; PROTEINS; SEPARATION;

ALANYL PEPTIDE NUCLEIC ACIDS; BASE PAIR STACKING; REGIOISOMERS; SIDE CHAIN HOMOLOGATION;

OLIGOMERS;

PEPTIDE NUCLEIC ACID;

ARTICLE; BASE PAIRING; CHEMICAL STRUCTURE; CHEMISTRY; CIRCULAR DICHROISM; CONFORMATION; HYDROGEN BOND; METABOLISM;

BASE PAIRING; CIRCULAR DICHROISM; HYDROGEN BONDING; MODELS, MOLECULAR; MOLECULAR STRUCTURE; NUCLEIC ACID CONFORMATION; PEPTIDE NUCLEIC ACIDS;

EID: 16244408925     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b411545g     Document Type: Article

References (36)

1. Nucleic Acid Structure, ed. S. Neidle, Oxford University Press, Oxford, 1999.
2. C. Branden and J. Tooze, Introduction to Protein Structure, Garland Publishing, New York, 1999.
3. J. Hunziker, H.-J. Roth, M. Böhringer, A. Giger, U. Diederichsen, M. Göbel, R. Krishnan, B. Jaun, C. Leumann and A. Eschenmoser, Helv. Chim. Acta, 1993, 76, 259.
4. A. Eschenmoser and M. Dobler, Helv. Chim. Acta, 1992, 75, 218.
5. U. Diederichsen, in Bioorganic Chemistry - Highlights and New Aspects, ed. U. Diederichsen, T. Lindhorst, L. A. Wessjohann and B. Westermann, Wiley-VCH, Weinheim, 1999, pp. 255-261.
6. (a) U. Diederichsen, Angew. Chem., 1996, 108, 458;
7. (b) U. Diederichsen, Angew. Chem., Int. Ed. Engl., 1996, 35, 445.
8. (a) U. Diederichsen, Angew. Chem., 1997, 109, 1966;
9. (b)U. Diederichsen, Angew. Chem., Int. Ed. Engl., 1997, 36, 1886.
10. U. Diederichsen, Bioorg. Med. Chem. Lett., 1997, 7, 1743.
11. (a) U. Diederichsen, Angew. Chem., 1998, 110, 2395;
12. (b) U. Diederichsen, Angew. Chem., Int. Ed., 1998, 37, 2273.
13. U. Diederichsen and D. Weicherding, SYNLETT, 1999, S1, 917.
14. (a) J. Gante, Angew. Chem., 1994, 106, 1780;
15. (b) J. Gante, Angew. Chem., Int. Ed. Engl., 1994, 33, 1699.
16. R. Declercq, A. van Aerschot, R. J. Read, P. Herdewijn and L. van Meervelt, J. Am. Chem. Soc., 2002, 124, 928.
17. M. Böhringer, H.-J. Roth, J. Hunziker, M. Göbel, R. Krishnen, A. Giger, B. Schweizer, J. Schreiber, C. Leumann and A. Eschenmoser, Helv. Chim. Acta, 1992, 75, 1416.
18. B. Hyrup, M. Egholm, M. Rolland, R. H. Berg, P. E. Nielsen and O. Buchardt, J. Chem. Soc., Chem. Commun., 1993, 518.
19. B. Hyrup, M. Egholm, P. E. Nielsen, P. Wittung, B. Norden and O. Buchardt, J. Am. Chem. Soc., 1994, 116, 7964.
20. P. Lohse, B. Oberhauser, B. Oberhauser-Hofbauer, G. Baschang and A. Eschenmoser, Croat. Chim. Acta, 1996, 69, 535.
21. L. D. Arnold, T. H. Kalantar and J. C. Vederas, J. Am. Chem. Soc., 1985, 107, 7105.
22. L. D. Arnold, R. G. May and J. C. Vederas, J. Am. Chem. Soc., 1988, 110, 2237.
23. A. Lenzi, G. Reginato and M. Taddei, Tetrahedron Lett., 1995, 36, 1713.
24. A. Lenzi, G. Reginato, M. Taddei and E. Trifilieff, Tetrahedron Lett., 1995, 36, 1717.
25. P. Ciapetti, A. Mann, A. Schoenfelder, M. Taddei, E. Trifilieff, I. Canet and J. L. Canet, Lett. Peptide Sci. 1997, 4, 341.
26. P. Ciapetti, F. Soccolini and M. Taddei, Tetrahedron, 1997, 53, 1167.
27. (a) R. Appel, Angew. Chem., 1975, 87, 863;
28. (b) R. Appel, Angew. Chem., Int. Ed. Engl., 1975,14, 801.
29. U. Diederichsen and H. W. Schmitt, Tetrahedron Lett., 1996, 37, 475.
30. The preference of A-T pairing alanyl-PNA for the reverse Watson-Crick or reverse Hoogsteen mode was investigated by 2,6-diaminopurine/thymine alanyl-PNA hexamers. The reverse Watson-Crick mode of diaminopurine/thymine is formed with three hydrogen bonds whereas the reverse Hoogsteen mode is only bidentate. Since diaminopurine/thymine alanyl-PNA hexamers provided comparable stabilities to the A/T alanyl-PNA the reverse Hoogsteen mode is likely to be formed in both cases.
31. Maruzen HGS Molecular Structure Model, Tokyo, Japan.
32. R. E. Dickerson, in Nucleic Acid Structure, ed. S. Neidle, Oxford University Press, Oxford, 1999, pp. 145-197.
33. U. Heinemann and C. Alings, J. Mol. Biol., 1989, 210, 369.
34. U. Diederichsen and H. W. Schmitt, Angew. Chem., 1998, 110, 312.
35. (a) A. M. Brückner, P. Chakraborty, S. H. Gellman and U. Diederichsen, Angew. Chem., 2003, 115, 4532;
36. (b) A. M. Brückner, P. Chakraborty, S. H. Gellman and U. Diederichsen, Angew. Chem., Int. Ed., 2003, 42, 4395.