Survey of the proton affinities of adenine, cytosine, thymine and uracil dideoxyribonucleosides, deoxyribonucleosides and ribonucleosides

✍ Scribed by Liguori, Angelo; Napoli, Anna; Sindona, Giovanni

• Publisher: John Wiley and Sons
• Year: 2000
• Tongue: English
• Weight: 83 KB
• Volume: 35
• Category: Article
• ISSN: 1076-5174
• DOI: 10.1002/(sici)1096-9888(200002)35:2<139::aid-jms921>3.0.co;2-a

✦ Synopsis

The kinetic method was applied to the determination of the proton affinities (PAs) of modified deoxy-and dideoxyribonucleosides. A correlation between the measured PAs and the replacement of one of the three hydroxyl groups of the ribose unit is presented. A PA scale was obtained which shows that the replacement of the primary or of one or both secondary hydroxyl groups of a ribonucleoside with a hydrogen atom induces the lowering or the enhancement of the nucleoside PA, respectively. The scale extends over a very narrow range of ∼2 kcal mol -1 , thus demonstrating the sensitivity of the kinetic method in the evaluation of small differences in thermodynamic parameters.