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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 6, Number 1
January 20, 1985 

Charge-Transfer Complexing Properties of 1-Methyl Nicotinamide and Adenine in Relation to the Intramolecular Interaction in Nicotinamide Adenine Dinucleotide (NAD+)
Joon Woo Park, Young Hee Paik
The charge-transfer complexing properties of 1-methyl nicotinamide (MNA), an acceptor, and adenine, a donor, were investigated in water and SDS micellar solutions in relation to the intramolecular interaction in nicotinamide adenine dinucleotide (NAD+). The spectral and thermodynamic parameters of MNA-indole and methyl viologen-adenine complex formations were determined, and the data were utilized to evaluate the charge-transfer abilities of MNA and adenine. The electron affinity of nicotinamide was estimated to be 0.28 eV from charge-transfer energy of ∼300 nm for MNA-indole. The large enhancement of MNA-indole complexation in SDS solutions by entropy effect was attributed to hydrophobic nature of indole. The complex between adenine and methyl viologen showed an absorption band peaked near 360 nm. The ionization potential of adenine was evaluated to be 8.28 eV from this. The much smaller enhancement of charge-transfer interaction involving adenine than that of indole in SDS solutions was attributed to weaker hydrophobic nature of the donor. The charge-transfer energy of 4.41 eV (280 nm) was estimated for nicotinamide-adenine complex. The spectral behaviors of NAD+ were accounted to the presence of intramolecular interaction in NAD+, which is only slightly enhanced in SDS solutions. The replacement of nicotinamide-adenine interaction in NAD+ by intermolecular nicotinamide-indole interaction in enzyme bound NAD+, and guiding role of adenine moiety in NAD+ were discussed.
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