Non-enzymic reactions of indoles with pyridine coenzymes and related structures

Alivisatos, Spyridon G.A.; Ungar, Frieda; Jibril, Abbas Othman; Mourkides, G. A.

doi:10.1016/0006-3002(61)90178-0

Cited by 49 publications

(16 citation statements)

References 24 publications

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“…Indole derivatives form donor-acceptor (charge-transfer) complexes with a variety of aromatic electron acceptors (Harbury & Foley, 1958;Isenberg & Szent-Gy6rgyi, 1958;Fujimori, 1959;Alivisatos, Ungar, Jibril & Mourkides, 1961 ;Cilento & Tedeschi, 1961;Foster & Hanson, 1964;Wilson, 1966;Shifrin, 1968;Shinitzky & Katchalski, 1968;Montenay-Garestier & H616ne, 1971), and charge-tranfer interactions have been implicated in such biological processes as the binding of nicotinamide (Alivisatos, Ungar, Jibril & Mourkides, 1961;Cilento & Tedeschi, 1961;Shifrin, 1968) and flavin (Harbury & Foley, 1958;Isenberg & Szent-Gy6rgyi, 1958;Wilson, 1966) coenzymes to tryptophan residues of en-0 0 zymes; interactions of indoles with nucleotides and with nucleic acids (Shinitzky & Katchalski, 1968;Montenay-Garestier & H616ne, 1971); and binding of serotonin and hallucinogenic tryptamines to synaptic receptor sites (Szent-Gy6rgyi, 1960). To obtain information about the structural factors involved in indole interactions with aromatic acceptors, we are currently examining a series of crystal structures in which indole derivatives are complexed with picric acid.…”

Section: Introductionmentioning

confidence: 99%

Crystal structures of tryptamine picrate and D,L-tryptophan picrate–methanol, two indole donor–acceptor complexes

Gartland¹,

Freeman²,

Bugg³

1974

Acta Crystallogr Sect B

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The crystal structures of the red picric acid salts of tryptamine and of D,L-tryptophan-methanol were determined by X-ray diffraction methods. Crystals of tryptamine picrate (C10HIaN2.C6H2N307) are monoclinic, space group P21/c, with a= 15.927 (2), b=6.913 (1), c=21.841 (2) A, fl= 133.88 (1) ° and Z= 4. Crystals of O,L-tryptophan picrate-methanol (C11HI3N202. C6H2N307. CH40) are triclinic, space group P1, with a= 11-733 (1), b= 11-547 (1), c=7.971 (1) ,~, a= 100.34 (3), fl=81.31 (1), y=97.98 (2) °, and Z--2. Three-dimensional X-ray intensity data (2882 reflections for the tryptamine complex and 3458 reflections for the tryptophan complex) were measured with an automated diffractometer by use of nickel-filtered copper radiation. Trial structures, obtained by direct methods, were refined by leastsquares calculations to R indices of 0.056 and 0.088 for the tryptamine and tryptophan complexes, respectively. Both crystal structures contain distinct indole-picrate pairs. The indole and picrate planes are stacked, with interplanar spacings of 3.3-3.5 A. The stacking interaction appears to be of the donoracceptor (charge-transfer) type. However, contrary to the continous columns of stacked rings usually found in crystal structures of aromatic donor-acceptor complexes, the stacked indole-picrate pairs are relatively isolated and without re-re interactions between adjacent pairs. The stacking patterns are similar in the tryptamine and tryptophan complexes. The tryptamine and tryptophan cations assume the same conformation found for serotonin in the crystal structure of the serotonin picrate monohydrate donor-acceptor complex.

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Section: Introductionmentioning

confidence: 99%

Crystal structures of tryptamine picrate and D,L-tryptophan picrate–methanol, two indole donor–acceptor complexes

Gartland¹,

Freeman²,

Bugg³

1974

Acta Crystallogr Sect B

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“…Alivisitos el al. (6) have also observed the difference in magnitude of K between indole-NAD+ and some indole derivative-NAD+ con~plexes, although no definite explanation has been drawn by them regarding the origin of such differences. I n order to arrive at a more definite conclusion, we have not only studied the conlplex fortuation between the three aron~atic ailxino acids and indole with MCP and NAD+ respectively by spectrophotolnetric methods but also have done molec~~lar orbital calculations on the system.…”

Section: Resultsmentioning

confidence: 99%

“…A more detailed study of nonenzymatic interactions of various indoles with NAD+ has been carried out by Alivisitos et,al. (6). Their spectral data indicate a 1 : 1 stoichionletry for the complexes, and the association constants for indoles with a side chain at the 3-position are found to be 3 to 4 times larger than those obtained for the indole-NADf complex.…”

Section: Introductionmentioning

confidence: 89%

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Donor–acceptor interactions in biomolecules. II. Spectroscopic and molecular orbital studies of amino acid – nicotinamide adenine dinucleotide complexes

Nagchaudhuri¹,

Suri²

1976

Can. J. Chem.

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JAYANTI NAGCHAUDHURI and RASHMI SURI. Can. J. Chern. 54, 59 (1976).The nature of complex formation between aromatic amino acids and some of their components with NADi (nicotinamide adenine dinucleotide) have been studied by spectropliotometric methods. A comparison of the stability of these complexes with that of the complexes of the same donors with a model compound of NAD+ i.e. N-metl~yl-3-carboxamide pyridinium chloride (MCP) has been carried out by examining the type of complexes formed and their geometry. Simple molecular orbital calculations have been done to determine the quantity of charge transfer 6Q and stabilization energy 6E and to show the significance of mutual orientation of donor and acceptor in determining the stability. The enhanced stability of tryptophanNADi complex in comparison to indole-NADi complex Iias also been explained.

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“…The demonstration that a complex is formed between auxins and pyridine nucleotides and the discovery that such complexes are inhibitory to certain PN-requiring dehydrogenases (1,2,6) has made it desirable to explore the possibilities that such a complex might be either uniquely or preferentially a cofactor for some key reaction(s) in the metabolic sequence leading to the growth of plant cells. Metabolic control, exerted through such a hypothetical cofactor, could open normally quiescent pathways in response to the provision of either endogenous or exogenous auxin and result in a growth response by supplying substrates for growth reactions, or by providing energy in a form particularly suited for the growth process.…”

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confidence: 99%

Interaction of Nucleotides with Auxins in Growth of Pea Stem Segments

Wedding

Black

1964

Plant Physiol.

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The demonstration that a complex is formed between auxins and pyridine nucleotides and the discovery that such complexes are inhibitory to certain PN-requiring dehydrogenases (1, 2, 6) has made it desirable to explore the possibilities that such a complex might be either uniquely or preferentially a cofactor for some key reaction (s) Since purine-containing compounds such as kinetin and adenine have been shown to have effects on growth, dry matter production, protein synthesis and morphological characteristics of plants (4), and since the auxin-PN complex is probably formed through the purine moiety of the nucleotides (1, 2), the possibility exists that any observed effect of the nucleotides on growth might be due to their conversion to kinin-like compounds.Experiments designed to provide information relating to these questions have been carried out using the increase in fresh weight of pea epicotyl segments (3) as an assay for growth response. Materials and MethodsThe plant material used was Pisum sativum, L., var. Alaska. The growth assay was an adaptation of that used by Galston and Hand (3).

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Non-enzymic reactions of indoles with pyridine coenzymes and related structures

Cited by 49 publications

References 24 publications

Crystal structures of tryptamine picrate and D,L-tryptophan picrate–methanol, two indole donor–acceptor complexes

Crystal structures of tryptamine picrate and D,L-tryptophan picrate–methanol, two indole donor–acceptor complexes

Donor–acceptor interactions in biomolecules. II. Spectroscopic and molecular orbital studies of amino acid – nicotinamide adenine dinucleotide complexes

Interaction of Nucleotides with Auxins in Growth of Pea Stem Segments

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