Self-pairing PNA with alternating alanyl/homoalanyl backbone

Tetrahedron Letters

Volumn 37, Issue 4, 1996, Pages 475-478

  Diederichsen, Ulf ^a   Schmitt, Harald W ^a  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; BASE PAIRING; CIRCULAR DICHROISM; MODEL; ULTRAVIOLET SPECTROPHOTOMETRY;

EID: 0030070565     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02216-3     Document Type: Article

References (12)

1. The name Peptide Nucleic Acid (PNA) was introduced by Buchard and Nielsen for an oligomer containing a polyamide with nucleobase substituted side chains. (For a discussion of the 'not strictly chemically correct name' see Nielsen, P. E.; Egholm, M.; Buchardt, O.; Bioconjugate Chem. 1994, 5, 3 .). The abbreviation PNA is common today at least for the description of the Nielsen-type of oligomer. We decided to use the abbreviation PNA for our oligomers as well, since our backbone is a real peptide and the functionality for recognition and storage of information is based on the DNA/RNA nucleobases. In this way PNA is a chimera between peptides and nucleic acids. Peptide nucleic acid (PNA) was used for nucleo homoalanyl oligomers before. (Lenzi, A.; Reginato, G.; Taddei, M.; Tetrahedron Lett. 1995, 36, 1713.) Garner suggests 'Peptide based Nucleic Acid surrogates (PNA). (Garner, P.; Yoo, J. U.; Tetrahedron Lett. 1993, 34, 1275.)
2. The name Peptide Nucleic Acid (PNA) was introduced by Buchard and Nielsen for an oligomer containing a polyamide with nucleobase substituted side chains. (For a discussion of the 'not strictly chemically correct name' see Nielsen, P. E.; Egholm, M.; Buchardt, O.; Bioconjugate Chem. 1994, 5, 3 .). The abbreviation PNA is common today at least for the description of the Nielsen-type of oligomer. We decided to use the abbreviation PNA for our oligomers as well, since our backbone is a real peptide and the functionality for recognition and storage of information is based on the DNA/RNA nucleobases. In this way PNA is a chimera between peptides and nucleic acids. Peptide nucleic acid (PNA) was used for nucleo homoalanyl oligomers before. (Lenzi, A.; Reginato, G.; Taddei, M.; Tetrahedron Lett. 1995, 36, 1713.) Garner suggests 'Peptide based Nucleic Acid surrogates (PNA). (Garner, P.; Yoo, J. U.; Tetrahedron Lett. 1993, 34, 1275.)
3. The name Peptide Nucleic Acid (PNA) was introduced by Buchard and Nielsen for an oligomer containing a polyamide with nucleobase substituted side chains. (For a discussion of the 'not strictly chemically correct name' see Nielsen, P. E.; Egholm, M.; Buchardt, O.; Bioconjugate Chem. 1994, 5, 3 .). The abbreviation PNA is common today at least for the description of the Nielsen-type of oligomer. We decided to use the abbreviation PNA for our oligomers as well, since our backbone is a real peptide and the functionality for recognition and storage of information is based on the DNA/RNA nucleobases. In this way PNA is a chimera between peptides and nucleic acids. Peptide nucleic acid (PNA) was used for nucleo homoalanyl oligomers before. (Lenzi, A.; Reginato, G.; Taddei, M.; Tetrahedron Lett. 1995, 36, 1713.) Garner suggests 'Peptide based Nucleic Acid surrogates (PNA). (Garner, P.; Yoo, J. U.; Tetrahedron Lett. 1993, 34, 1275.)
4. Diederichsen, U.; Angew. Chem., submitted.
5. 2 (lysineamide), The amino acids with D-configuration are underlined.
6. Carpino, L. A.; El-Faham, A.; Minor, C. A.; Albericio, F.; J. Chem. Soc., Chem. Commun. 1994, 201.
7. a) Lenzi, A.; Reginato, G.; Taddei, M.; Tetrahedron Lett. 1995, 36, 1713.
8. b) Lenzi, A.; Reginato, G.; Taddei, M.; Trifilieff, E.; Tetrahedron Lett. 1995, 36, 1717.
9. a) Lohse, P.; Synthese und Eigenschaften von Nukleodipeptamidinium-Salzen; thesis Nr. 9937 in the laboratory of A. Eschenmoser; ETH Zürich 1992.
10. b) Lohse, P; Oberhauser, B.; Oberhauser-Hofbauer, B.; Eschenmoser, A.; Croatica Chim. Acta, in press.
11. Nielsen, P. E.; Egholm, M.; Berg, R. H.; Buchardt, O.; Science 1991, 254, 1497.
12. 2O): δ (ppm) 8.29-8.15 (m, 6H, H2, H8 adenine), 7.36-7.31 (m, 2H, H6 thymine), 7.25 (s, 1H, H6 thymine), 4.58-3.75 (m, 19H, Hα, Hβ alanine, Hγ homoalanine), 2.92 (t, 2H, J=8.1 Hz, Hε Lys), 2.50-2.05 (m, 6H, Hβ homoalanine), 1.85-1.55 (m, 4H Lys), 1.65 (s, 6H, thymine), 1.57 (s, 3H, thymine), 1.34 (m, 2H, Lys).