Alkylation of Adenine, Adenosine, and NAD+ with 1,3-Propanesultone. Synthesis of N6-(3-sulfonatopropyl)-NAD+, a new NAD+ derivative with substantial coenzyme activity
✍ Scribed by Gianconno Carrea; Gianluca Ottolina; Sergio Riva; Bruno Danieli; Giordano Lesma; Giovanni Palmisano
- Publisher
- John Wiley and Sons
- Year
- 1988
- Tongue
- German
- Weight
- 727 KB
- Volume
- 71
- Category
- Article
- ISSN
- 0018-019X
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✦ Synopsis
The reactivity of 1,3-propanesultone with adenine, adenosine, and NAD+ was studied in order to prepare N6-(3-sulfonatopropy1)-NAD+ (3b), a new NAD' derivative substituted at the purine moiety with substantial coenzyme activity for several dehydrogenases. The regiochemistry of the alkylation at the purine nucleus was investigated by UV, 'H-NMR, and FAB-MS. FAB-MS proved to be a powerful tool for determining the molecular weight of these polar and poorly volatile compounds. In addition, regular fragmentation of 3b and other NAD' derivatives was observed.
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Minor yields were observed in the absence of the proton scavenger.