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Issue 7, 1994
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Regioselective addition of 2-nitropropane anion to NAD+ analogues

Shunichi Fukuzumi,  Morifumi Fujita,  Junichi Maruta  and  Michel Chanon 

Abstract

Various NAD+ analogues have been reduced regioselectively by the tetramethylammonium salt of 2-nitropropane anion in acetonitrile at 298 K to yield the corresponding 4-alkylated NADH analogues. The one-electron oxidation potential of the tetramethylammonium salt of 2-nitropropane anion has been determined as 0.10 V (vs. SCE) by using second harmonic ac voltammetry as well as by analysing the cyclic voltammograms at various sweep rates. The rate constants for the reduction of NAD+ analogues by 2-nitropropane anion (>1 × 106 dm3 mol–1 s–1) are much larger than those estimated for outer-sphere electron transfer from 2-nitropropane anion to NAD+ analogues based on the one-electron oxidation potential of 2-nitropropane anion and the one-electron reduction potentials of NAD+ analogues. The origin of the regioselectivity is discussed in terms of the HSAB (hard and soft acids and bases) principle.

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Article type: Paper
DOI: 10.1039/P29940001597
Citation: J. Chem. Soc., Perkin Trans. 2, 1994,0, 1597-1602
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    Regioselective addition of 2-nitropropane anion to NAD+ analogues

    S. Fukuzumi, M. Fujita, J. Maruta and M. Chanon, J. Chem. Soc., Perkin Trans. 2, 1994, 0, 1597
    DOI: 10.1039/P29940001597

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