A simple glycol nucleic acid

Journal of the American Chemical Society

Volumn 127, Issue 12, 2005, Pages 4174-4175

  Zhang, Lilu ^a   Peritz, Adam ^a   Meggers, Eric ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCOL NUCLEIC ACID; NUCLEIC ACID; UNCLASSIFIED DRUG;

ARTICLE; BASE PAIRING; CATALYSIS; CIRCULAR DICHROISM; MELTING POINT; NUCLEIC ACID ANALYSIS; TEMPERATURE DEPENDENCE; THERMOSTABILITY; ULTRAVIOLET SPECTROSCOPY;

CIRCULAR DICHROISM; DNA; EPOXY COMPOUNDS; GLYCOLS; NUCLEIC ACIDS; NUCLEOTIDES; OLIGONUCLEOTIDES; PROPANOLS; RNA; STEREOISOMERISM;

EID: 16244417170     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja042564z     Document Type: Article

References (15)

1. For a review on the chemical etiology of nucleic acid structure, see: Eschenmoser, A. Science 1999, 284, 2118-2124.
2. For a review on oligonucleotide analogues with phosphodiester connectivity, see: Leumann, C. J. Bioorg. Med. Chem. 2002, 10, 841-854.
3. For oligonucleotide analogues containing an uncharged pseudopeptide backbone, see: (a) Nielsen, P. E. Acc. Chem. Res. 1999, 32, 624-630.
4. (b) Diederichsen, U. Angew. Chem., Int. Ed. Engl. 1997, 36, 1886-1889.
5. Schöning, K.-U.; Scholz, P.; Guntha, S.; Wu, X.; Krishnamurthy, R.; Eschenmoser, A. Science 2000, 290, 1347-1351.
6. For using the glycol backbone in a single metallo-nucleobase pair, see: Zhang, L.; Meggers, E. J. Am. Chem. Soc. 2005, 127, 74-75.
7. Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2001, 40, 2004-2021.
8. For related epoxide ring openings with nucleobases, see: (a) Baumgartner, H.; Marschner, C.; Pucher, R.; Griengl, H. Tetrahedron Lett. 1991, 32, 611-614.
9. (b) Ludek, O. R.; Meier, C. Synthesis 2003, 2101-2109.
10. Acyclic nucleotides have been demonstrated to strongly destabilize duplex DNA: (a) Schneider, K. C.; Benner, S. A. J. Am. Chem. Soc. 1990, 112, 453-455.
11. (b) Peng, L.; Roth, H.-J. Helv. Chim. Acta 1997, 80, 1494-1512.
12. For the concept of conformational restriction of nucleosides as a measure for preorganizing oligonucleotide single strands for duplex formation, see: (a) Tarköy, M.; Leumann, C. Angew. Chem., Int. Ed. Engl. 1993, 32, 1432-1434.
13. (b) Steffens, R.; Leumann, C. J. J. Am. Chem. Soc. 1999, 121, 3249-3255.
14. (c) Wengel, J. Acc. Chem. Res. 1999, 32, 301-310.
15. For a review on the origin of life, see: Orgel, L. E. Trends Biochem. Sci. 1998, 23, 491-495.