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Structural requirements of the flavin moiety of flavin-adenine dinucleotide for intramolecular complex formation

Structural requirements of the flavin moiety of flavin-adenine dinucleotide for intramolecular complex formation

Biochemistry 4(12): 2612-2615

Fluorescence quenching as a function of pH of solutions of analogs of riboflavin 5[image]-phosphate (FMN) and of flavin-adenine dinucleotide (FAD) has been examined to characterize the structural requirements for formation of the intramolecular donor-acceptor complex in the dinucleotide. The 3-methyl analog of FMN is nearly as fluorescent as FMN, and the corresponding derivative of FAD can form an intramolecular complex which appears similar to FAD. The 6,7-dichloro analog of FMN is considerably less fluorescent, and its FAD analog does not appear to complex well intramolecularly. Flavin-adenine(1-N-oxide) dinucleotide is unable to exist as a stable intramolecular complex. Since replacements of the glycityl chains of FMN analogs with [omega] -hydroxyalkyl substituents result in some increases of fluorescence, a slight quenching effect may be attributable to secondary hydroxyl groups. The 4[image]-hydroxybutyl, 5[image]-hydroxypentyl, and 6[image]-hydroxyhexyl analogs of FAD form intramolecular complexes with pH stabilities essentially identical with that of FAD. The 3[image]-hydroxypropyl, DL-glycero, D-erythro, and D-allo analogs of FMN are as fluorescent as FMN, but the corresponding FAD analogs appear to have steric restrictions which prevent formation of intramolecular complexes. As found earlier for FAD, in all cases where intramolecular complexing of FAD analogs can occur neutral to slightly acid conditions allow complexing, whereas strong acid decreases association by protonating both the 6-amino group of adenine and the flavin.

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Accession: 025531598

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PMID: 5880673

DOI: 10.1021/bi00888a010

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