The Strength of the Anomeric Effect in Adenosine, Guanosine, and in Their 2′-Deoxy Counterparts is Medium-Dependent

Journal of Organic Chemistry

Volumn 62, Issue 25, 1997, Pages 8800-8808

  Luyten, Ingrid ^a   Thibaudeau, Christophe ^a   Chattopadhyaya, Jyoti ^a  

^a UPPSALA UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0006484295     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971350f     Document Type: Article

References (31)

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22. In our search for the most pseudoequatorially oriented aglycon we have quantified the thermodynamics of a few other unnatural C-nucleosides, and they all show less pronounced pseudoequatorial C-aglycon than 9-deazaadenin-9-yl in 9-deaazaadenosine: 1-Deoxy-1-phenyl-β-D-ribofuranose (ΔH° = -5.4 kJ/mol ΔG° = -28 kJ/mol), 1-Deoxy-1-naphthyl-β-D-ribofuranose (ΔH° = 0.4 kJ/mol ΔG° = -0.4 kJ/mol), 1-Deoxy-1-(p-aminophenyl)-β-D-ribofuranose(ΔH° = -7.3 kJ/ mol ΔG° = -3.4 kJ/mol), 5-(β-D-ribofuranosyl)-2-bromopyridine (ΔH° = -44 kJ/mol ΔG° = -3.1 kJ/mol), 3-(β-D-ribofuranosyl)-2-fluoropyridine (ΔH° = 0.4 kJ/mol, ΔG° = -1.1 kJ/mol), 5-(β-D-ribofuranosyl)py- ridin-2-one (ΔH° = -5.6 kJ/mol, ΔG° = -3.4 kJ/mol),), 3-(β-D-ribofuranosyl)pyridin-2-one (ΔH° = -0.1 kJ/mol, ΔG° = -0.3 kJ/mol).
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25. For references to the PSEUROT v.5.4 program, see (a) Altona, C.; Francke, R.; de Haan, R.; Ippel, J. H.; Daalmans, G. J.; Westra, Hoekzema, A. J. A.; van Wijk, J. Magn. Res. Chem. 1994, 32, 670. (b) Donders, L. A.; de Leeuw, F. A. A. M.; Altona, C. Magn. Reson. Chem. 1989, 27, 556. (c) Altona, C.; Ippel, J. H.; Erkelens, C.; Groesbeek, G.; Donders, L. A. Magn. Res. Chem. 1989, 27, 564.
26. For references to the PSEUROT v.5.4 program, see (a) Altona, C.; Francke, R.; de Haan, R.; Ippel, J. H.; Daalmans, G. J.; Westra, Hoekzema, A. J. A.; van Wijk, J. Magn. Res. Chem. 1994, 32, 670. (b) Donders, L. A.; de Leeuw, F. A. A. M.; Altona, C. Magn. Reson. Chem. 1989, 27, 556. (c) Altona, C.; Ippel, J. H.; Erkelens, C.; Groesbeek, G.; Donders, L. A. Magn. Res. Chem. 1989, 27, 564.
27. m(S)).
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