3-(9-Adenyl)propionyltryptamine monohydrate

Ohki, M.; Takénaka, Akio; Shimanouchi, Hirotaka; Sasada, Yoshio

doi:10.1107/s0567740877009959

Cited by 13 publications

(4 citation statements)

References 2 publications

(2 reference statements)

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“…34 The DFT calculations were performed using the GAUSSIAN98 program package. 35 The single-point calculations used the B3LYP hybrid functional and the 6-311+G-(2df,p) basis set based on structures optimized using the 6-31+G(d) basis set with a starting geometry obtained from the X-diffraction data, 15 unless stated otherwise explicitly. In combination with the NoSymm option of GAUSSIAN98, the eigenvectors (principal directions) of the calculated dipolar coupling principal values are directly comparable with the experimental results.…”

Section: Methodsmentioning

confidence: 99%

“…Single crystals of C‚NFG are orthorhombic with space group Pna2 1 . 15 The crystallographic axes were used as reference axes in this study. The unit cell consists of four asymmetric units, interconnected by hydrogen bonding.…”

Section: Methodsmentioning

confidence: 99%

“…All crystals used were examined using X-ray diffraction methods, and the cell parameters agreed well with the published data. 15 2.2. Room-Temperature Experiments.…”

Section: Methodsmentioning

confidence: 99%

“…However, the literature contains very few examples of such complexes which have been well characterized structurally. [15][16][17] Evidently, the small number is due to the inherent difficulty of preparing crystals of complexes with constituents exhibiting significantly different physiochemical properties. The present work is a report of our first attempt in this direction.…”

Section: Introductionmentioning

confidence: 99%

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Electron Transfer in Amino Acid·Nucleic Acid Base Complexes: EPR, ENDOR, and DFT Study of X-Irradiated N-Formylglycine·Cytosine Complex Crystals

Sagstuen

Vågane

et al. 2006

J. Phys. Chem. A

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Single crystals of the 1:1 complex of the nucleic acid base cytosine and the dipeptide N-formylglycine (C.NFG) have been irradiated at 10 and 273 K to doses of about 70 kGy and studied at temperatures between 10 and 293 K using 24 GHz (K-band) and 9.5 GHz (X-band) electron paramagnetic resonance (EPR), electron nuclear double resonance (ENDOR), and ENDOR-induced EPR (EIE) spectroscopy. In this complex, the cytosine base is hydrogen bonded at positions N3 and N4 to the carboxylic group of the dipeptide, and the N3 position of cytosine has become protonated by the carboxylic group. At 10 K, two major radicals were characterized and identified. One of these (R1) is ascribed to the decarboxylated N-formylglycine one-electron oxidized species. The other (R2) is the N3-protonated cytosine one-electron reduced species. A third minority species (R3) appears to be a different conformation or protonation state of the one-electron reduced cytosine radical. Upon warming, the R2 and R3 radicals decay at about 100 K, and at 295 K, the only cytosine-centered radicals present are the C5 and C6 H-addition radicals (R5, R6). The R1 radical decays at about 150 K, and a glycine backbone radical (R4) grows in slowly. Thus, in the complex, a complete separation of initial oxidation and reduction events occurs, with oxidation localized at the dipeptide moiety, whereas reduction occurs at the nucleic acid base moiety. DFT calculations indicate that this separation is driven by large differences in electron affinities and ionization potentials between the two constituents of the complex. Once the initial oxidation and reduction products are trapped, no further electron transfer between the two constituents of the complex takes place.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

“…All crystals used were examined using X-ray diffraction methods, and the cell parameters agreed well with the published data. 15 2.2. Room-Temperature Experiments.…”

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Electron Transfer in Amino Acid·Nucleic Acid Base Complexes: EPR, ENDOR, and DFT Study of X-Irradiated N-Formylglycine·Cytosine Complex Crystals

Sagstuen

Vågane

et al. 2006

J. Phys. Chem. A

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Crystal and molecular structure of 9‐vinyladenine

Scharfenberg‐Pfeiffer

Kretschmer

Hoffmann

1988

Cryst. Res. Technol.

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The title compound 9-vinyladenine crystallizes in the monoclinic space group C2/c with 16molecules in the unit cell and the lattice parameters a = 13.682, b = 10.260, c = = 21.674 A, /? = 97.72". The crystal structure has been determined by direct methods and refined by full matrix least squares calculations up to the discrepancy factor R = 0.045.The two symmetry independent molecules differ in the orientation of the vinyl group relative to the adenine frame.Die Titelverbindung 9-Vinyladenin kristallisiert, in der monoklinen Raumgruppe C 2 / c mit 16 Molekulen in der Elementarzelle und den Gitterkonstanten a = 13,682, b = 10,250, e = 21,674 A, /I = 97,72". Die Kristallstruktur wurde mit direkten Methoden bestimmt und mit der Methode der kleinsten Quadrate bis zu einem R-Wert von 0,045 verfeinert.Die zwei symmetrieunabhangigen Molekule unterscheiden sich in der Orientierung der Vinylgruppe relativ zum Adeninkfirper.

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Aadmpy10 - Bidrub10

Sundaralingam¹,

Haromy²

Crystallographic and Structural Data I

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3-(9-Adenyl)propionyltryptamine monohydrate

Cited by 13 publications

References 2 publications

Electron Transfer in Amino Acid·Nucleic Acid Base Complexes: EPR, ENDOR, and DFT Study of X-Irradiated N-Formylglycine·Cytosine Complex Crystals

Electron Transfer in Amino Acid·Nucleic Acid Base Complexes: EPR, ENDOR, and DFT Study of X-Irradiated N-Formylglycine·Cytosine Complex Crystals

Crystal and molecular structure of 9‐vinyladenine

Aadmpy10 - Bidrub10

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