A new base-pairing motif based on modified guanosines

Angewandte Chemie - International Edition

Volumn 37, Issue 12, 1998, Pages 1726-1729

  Sessler, Jonathan L ^a   Wang, Ruizheng ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

Base pairing; Guanosine; Hydrogen bonds; Molecular recognition; Supramolecular chemistry

Indexed keywords

EID: 0032479404     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19980703)37:12<1726::AID-ANIE1726>3.0.CO;2-X     Document Type: Article

References (25)

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10. a) For a modified adenine that forms four-point hydrogen bonds with guanine, see G. A. Leonard, A. Guy, T. Brown, R. Teoulé, W. N. Hunter, Biochemistry 1992, 31, 8415; b) for a uracil whose carbonyl group accepts two N-H⋯O hydrogen bonds, see R. Taylor, O. Kennard, Acc. Chem. Res. 1984, 17, 320.
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13. A weak signal ascribable to a dimeric species was observed in the mass spectrum of 2. However, the signal in question was not sufficiently intense to allow for a high-resolution analysis.
14. 15N).
15. 3.
16. 6]DMSO).
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19. 2 proton provides evidence of close proximity of these two protons.
20. a) The syn conformation is also believed to play a critical role during the synthesis because only it allows the 8-position to be most susceptible to nucleophilic attack by its coupling partner;
21. b) both a syn conformation of the giycosidic bond and a cis configuration of the C=N bond are assigned to 6 on the basis of NMR spectral similarities.
22. The fact that the lone pairs of the two carbonyl oxygen atoms are tied up in hydrogen bonding is believed to contribute to the nonpolarity of 1.
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24. The insolubility of 1 under the conditions of the experiment precluded the use of the more strongly hydrogen bonding solvent water.
25. The coalescence observed at higher temperature is the result of fast exchanges between different states of DMSO-derived solvation of the four amino protons. This gives rise to an average chemical shift for these protons; at lower temperature, however, the relevant exchange processes are slow enough on the NMR time scale that multiple resonances are observed.