Nuclear magnetic resonance study of the confirmation of nicotinamide-adenine dinucleotide and reduced nicotinamide-adenine dinucleotide insolution

Catterall, William A.; Hollis, Donald P.; Walter, Charles

doi:10.1021/bi00838a021

Cited by 39 publications

(43 citation statements)

References 10 publications

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“…It is therefore predictable that positioning of the eadenosine of any fluorescent coenzyme moiety (e.q., EATP, EADP) in close proximity to a tryptophan in a protein will result in complete fluorescence quenching of the former. Accumulated evidence on the conformation of nicotinamide adenine dinucleotide, NAD+, and the reduced form, NADH, in neutral aqueous solution is consistent with a population of open forms, in which the ribose-diphosphate-ribose backbone is extended, and closed forms, in which the heterocyclic rings are "stacked" in close proximity (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14). Energy transfer from adenine to dihydronicotinamide in NADH in very dilute solution is compatible only with a structure in which the two heterocyclic rings are in close proximity (15,16 (25,26) with chloroacetaldehyde, thus providing a model in which indole is used as a neutral substitute for tryptophan.…”

mentioning

confidence: 91%

Dynamic and static quenching of 1,N6-ethenoadenine fluorescence in nicotinamide 1,N6-ethenoadenine dinucleotide and in 1,N6-etheno-9-(3-(indol-3-yl) propyl) adenine.

Gruber¹,

Leonard²

1975

Proc. Natl. Acad. Sci. U.S.A.

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For nicotinamide 1,N6-ethenoadenine dinucleotide (ENAD+), the fluorescent analog of NAD+, in neutral aqueous solution the quantum yield has been determined to be 0.028 and the fluorescent lifetime, 2.1 nsec. Simultaneous determination of quantum yields and lifetimes of eNAD+ and of the "half molecule" EAMP allows the calculation of the percentage of stacked and open conformations of the dinucleotide. At 250 in neutral aqueous solution there is 45 I 5% of stacked forms. The value of the fluorescent lifetime observed for ENAD+ is sensitive to fluorescent impurities, especially those containing the E-adenosine moiety, and a purification procedure using high performance liquid chromatography was devised to obtain fluorescently homogeneous preparations.In order to study the effect on e-adenosine fluorescence caused by the possible close proximity of a tryptophan in a polypeptide chain or protein, we have prepared 1,N6-etheno- These studies relate to intramolecular stacking interactions within the ENAD+ molecule and set a probable upper limit for the interactions within the NAD+ molecule itself. It is also important to delineate possible interactions between the adenosine moiety of various coenzymes and the individual amino acids, e.g., tryptophan, of various proteins. To do so on a simplified level we synthesized 1,N6-etheno-9-[3- (indol-3-yl)propyl]adenine (EAde9-Cs-Ind3) by reaction of 9-[3-(indol-3-yl)propyl]adenine (Ade9-C3-Ind3) (25, 26) with chloroacetaldehyde, thus providing a model in which indole is used as a neutral substitute for tryptophan. From simultaneous measurement of the fluorescence lifetime and the quantum yield of EAde9-C3-Ind3 relative to those of the "half molecules" 1,N6-etheno-9-propyladenine (EAde9-C3) and 3-propylindole (Ind3-Cs), we are able to predict the fluorescence quenching effect of bringing the E-adenine moiety into close proximity with the indole of tryptophan. (27.6 MPa). The eluate was monitored by absorbance at 254 nm, recorded on a Hewlett-Packard recorder modified as described previously (27). As a criterion of purity we used identical lifetimes determined by both phase shift and modulation (28,29). This technique is very sensitive to the presence of more than a single fluorescent decay, and the presence of EAMP in our preparation would be expected to 3966

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mentioning

confidence: 91%

Dynamic and static quenching of 1,N6-ethenoadenine fluorescence in nicotinamide 1,N6-ethenoadenine dinucleotide and in 1,N6-etheno-9-(3-(indol-3-yl) propyl) adenine.

Gruber¹,

Leonard²

1975

Proc. Natl. Acad. Sci. U.S.A.

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“…However, the molecule may exist either in an unfolded conformation or in a folded conformation with the two rings superimposed over each other. A folded conformation is observed for many coenzymes, examples being the pyridine dinucleotides (7)(8)(9)(10)(11)(12)(13)(14)(15) and flavin adenine dinucleotide (FAD) (16)(17)(18)(19). Besides these intramolecular interactions, intermolecular association equilibria must be considered.…”

Section: Introductionmentioning

confidence: 99%

Self Association of Folic Acid in Aqueous Solution by Proton Magnetic Resonance

Lam¹,

Kotowycz²

1972

Can. J. Chem.

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Proton magnetic resonance experiments on the disodium salt of folic acid in aqueous solutions (pD 7.1) indicate that the folate ion exists in an unfolded, extended conformation in solution. However, based on a temperature and concentration dependence of the proton chemical shifts, folate ions are involved in intermolecular association consisting of a vertical stacking interaction. A stacking model is proposed for the association with the hydrophilic ends of the molecule alternating in orientation with respect to the hydrophobic portion of the neighboring molecules.Les experiences de r.m.n. sur le sel dissodique de I'acide folique en solutions aqueuses (pD 7.1) indiquent que I'ion folate existe dans une conformation non plissie et itirie. Cependant, les risultats fondis sur I'influence de la tempirature et de la concentration sur les diplacements chimiques du proton montrent que les ions folates sont impliquts dans une association intermoliculaire rigie par une interaction due i un empilement vertical. Un modele pour cet entassement est proposi oh les bouts hydrophiliques de la molicule alternent en orientation avec la portion hydrophobique des molicules voisines.

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“…It is generally agreed that this association undergo considerable upfield shifts with increasing proceeds beyond the dimer stage. concentration, while at the same time the nicotinEarlier studies (4,8,13) had pointed out that the amide protons N2, N4, N5, and N 6 all undergo 'H nmr chemical shifts of NAD+ can vary with downfield shifts. It is interesting to note that the concentration; however, so far no attempts have chemical shifts of the Al' and N1' protons of the been made to obtain equilibrium constants from contiguous bases also change in opposite directions, the data.…”

Section: Materials and San~ple Preparationmentioning

confidence: 98%

“…Numerous nmr studies have been undertaken to investigate the dynamic conformation of p-nicotinamide adenine dinucleotide (NAD') in aqueous solution (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19). A detailed discussion of the existing nmr literature on this subject was made recently by Ellis and co-workers (20).…”

Section: Introductionmentioning

confidence: 99%

Specific binding of phenylalanine and tryptophan to β-nicotinamide adenine dinucleotide

Neurohr¹,

Mantsch²

1979

Can. J. Chem.

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This 1H nmr study provides the first experimental evidence for specific complex formation between the coenzyme nicotinamide adenine dinucleotide (β-NAD+) and the two aromatic amino acids phenylalanine and tryptophan. It is shown that the interaction is of the stacking type and occurs between the aromatic side chains of these amino acids and the adenine moiety of NAD+. Binding parameters were obtained from dilution studies, taking into account the self-association of NAD+. The apparent microscopic association constants for complex formation of phenylalanine and tryptophan with excess NAD+ in aqueous solutions are 1.35 M−1 and 11.35 M−1, respectively, indicating that the adenine moiety of NAD+ can discriminate between phenylalanine and tryptophan by a stronger binding to the latter. The results are discussed with regard to the interaction of NAD+ with dehydrogenases.

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Nuclear magnetic resonance study of the confirmation of nicotinamide-adenine dinucleotide and reduced nicotinamide-adenine dinucleotide insolution

Abstract: The findings reported here are consistent with the conclusion that the pyridine nucleotides can exist in solution as an equilibrium mixture of folded and unfolded forms. For

Cited by 39 publications

References 10 publications

Dynamic and static quenching of 1,N6-ethenoadenine fluorescence in nicotinamide 1,N6-ethenoadenine dinucleotide and in 1,N6-etheno-9-(3-(indol-3-yl) propyl) adenine.

Dynamic and static quenching of 1,N6-ethenoadenine fluorescence in nicotinamide 1,N6-ethenoadenine dinucleotide and in 1,N6-etheno-9-(3-(indol-3-yl) propyl) adenine.

Self Association of Folic Acid in Aqueous Solution by Proton Magnetic Resonance

Specific binding of phenylalanine and tryptophan to β-nicotinamide adenine dinucleotide

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