Aluminum chloride complexes with purine, adenine and guanine

Mikulski, Chester M.; Cocco, Susan; MATTUCCI, L.; DEFRANCO, N.; Weiss, Lynne; Karayannis, Nicholas M.

doi:10.1016/s0020-1693(00)85060-4

Cited by 27 publications

(8 citation statements)

References 43 publications

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“…Similar shifts for C(6) and C(8) have been reported for MeHg(II) complexes of guanosine and inosine 32 when binding occurs at the N(7) atom. Since similar shifts are also noted in the present study for C(6) and C (8) resonances with respect to magnitude and directions, the N(7) atom of PUR is suggested as the binding site for the ruthenium complex. The C(2) resonance shows negligible upfield shifts (0.1 ppm) indicating the non-participation of N(1) and N(3) atoms in coordination.…”

Section: Nmr and 1 H Nmr Spectrasupporting

confidence: 89%

“…The participation of ligand ring nitrogens in coordination is interpreted. [1][2][3][4][5][6][7][8][9] On the other hand, the NH 2 deformation modes of free ADN are only slightly shifted in the IR spectrum of the complex indicating the non-participation of the exocyclic N(6) nitrogen of the NH 2 group in coordination.…”

Section: Infrared Studiesmentioning

confidence: 99%

“…The imidazole nitrogen which is protonated in the neutral PUR is considered as the most likely binding site. 10 Although a crystal structure determination of PUR places the labile proton at N (7) in the crystal, 11 it is equally well established from 13 C NMR studies that the N(7)-H and N( 9)-H tautomers of PUR are of comparable energies. 12,13 The labile proton resides on a non-coordinated imidazole nitrogen in metal complexes with neutral PUR or ADN showing the vibration ν NH (im) ≈ 2690 W for PUR and ≈ 2910 W, 2595 W for AND.…”

Section: Infrared Studiesmentioning

confidence: 99%

“…PUR has no exocyclic group at C(6) site so there is no steric differences between N(1) and N(7) sites. 31 Hence, N (7) or N(9) in PUR, which are the most basic sites, are the possible coordination sites. 13 C NMR peak assignment 12 and chemical shift data are tabulated in Table 6.…”

Section: Nmr and 1 H Nmr Spectramentioning

confidence: 99%

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Interaction of carbonylchlorohydridotris (triphenylphosphine) ruthenium (II) with purine, adenine, cytosine and cytidine

Ghose

2004

Journal of Chemical Research

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Many heavy metal ions are toxic in nature and certain complexes show antineoplastic activity. The interaction of the metal ions with DNA constituents might cause these. The biologically important nucleic acids constituents provide potential binding sites for metal ions.As a number of factors are responsible for the ability of the various donor atoms of nucleosides and nucleotides to act as sites of complexation, it is difficult to predict the binding sites for metal ions in a metal complex. The present paper deals with studies of carbonylchlorohydridotris (triphenylphosphine) ruthenium (II) complex with purine (PUR), adenine (ADN), cytosine (CTS) and cytidine (CTD). Investigations were undertaken to examine any change in the potential binding sites of the ligands which were reported for simple metal ions due to the presence of the triphenylphosphine ligands which could create steric restrants. Experimental Materials: The chemicals used were of AnalaR grade. PUR, ADN, CTS, CTD and [(C 6 H 5 ) 3 P] 3 Ru(CO)(Cl)H were obtained from Aldrich Chemicals Company, Inc., U.S.A. Solvents were dried before use. All the reactions were carried out under dry N 2 . The light petroleum used had b.p. 60-80°C.Methods: IR spectra (KBr) were recorded on a Perkin-Elmer 783 spectrometer and electronic spectra (CHCl 3 ) on a Shimadzu UV 190 spectrometer. 1 H NMR and 13 C NMR spectra were measured with a JEOL spectrometer model FX 900 FTNMR using TMS in DMSO-d 6 as internal standard.Chloride and phosphorus were estimated gravimetrically. C, H and N analyses were determined by a Perkin-Elmer model 240c elemental analyser.Preparation of complexes: All the reactions were carried out under dry dinitrogen. All the ruthenium (II) complexes were prepared by a similar procedure.The complex was prepared by the addition of the appropriate ligand suspended in 25ml methanol to a continuously stirred solution of 0.500 g [RuHCl(CO)(PPh 3 )] in 5 ml dichloromethane in 1:1 ratio under nitrogen atmosphere. The mixture was refluxed for 30 min, then allowed to cool, filtered off and the resulting solid was washed with methanol and finally with petroleum ether and dried under reduced pressure. Yields were 80-90 %.

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Section: Nmr and 1 H Nmr Spectrasupporting

confidence: 89%

Section: Infrared Studiesmentioning

confidence: 99%

Section: Infrared Studiesmentioning

confidence: 99%

Section: Nmr and 1 H Nmr Spectramentioning

confidence: 99%

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Interaction of carbonylchlorohydridotris (triphenylphosphine) ruthenium (II) with purine, adenine, cytosine and cytidine

Ghose

2004

Journal of Chemical Research

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“…It may also combine with compounds containing phosphorus, e.g. with DNA and RNA (Matsumoto et al, 1976;Karlik et al, 1980) and with ATP (Wagatsuma, 1983) and purines (Mikulski et al, 1982), or with cell wall pectic substances (Wagatsuma, 1983).…”

Section: Introductionmentioning

confidence: 99%

Aluminium polyphosphate in the ectomycorrhizal fungus Suillus variegatus (Fr.) O. Kunze as revealed by energy dispersive spectrometry

Väre

1990

New Phytologist

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SUMMARYThe aluminium detoxification mechanism of an ectomycorrhizal fungus, Suillus variegatus (Fr.) O. Kunze, grown on Petri dishes was studied using an atomic absorption spectrometer (AAS) and scanning transmission electronmicroscope with an electron dispersion photometer (STEM-EDS). Higher concentrations of soluble Al in the growth medium resulted in abundant formation of aluminium polyphosphate granules in the hyphae, which have not been noted earlier in ectomycorrhizal fungi or in their mycorrhizas. EDTA washing and STEM-EDS demonstrated that the granules were mainly located in the cell walls. The results suggest that growth of the fungal mycelium decreased as a result of higher Al and lower P concentrations inside the cells, as measured by AAS. The aluminium polyphosphate granules also contained varying amounts of other elements such as Ca, Cl, K, S, and Si.

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Highly Enantioselective Catalytic Conjugate Addition of N‐Heterocycles to α,β‐Unsaturated Ketones and Imides

Gandelman

Jacobsen

2005

Angewandte Chemie

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Nitrogen-containing heterocycles and their derivatives have broad application in synthetic, materials, and biological chemistry, and as a result their synthesis and reactivity are subjects of considerable interest.[1] Generation of chiral Nheteroaromatic derivatives in optically active form is a challenging facet of this research area that has seen important, but somewhat uneven progress.[2] For example, neither stoichiometric nor catalytic asymmetric conjugate additions of nitrogen-centered nucleophiles based on N-heterocyclic structures has been developed, despite the impressive recent advances in the general area of 1,4-addition chemistry and the utility that the resulting products might hold. [3,4] Potential applications might include preparation of novel non-natural nucleosides (NNNs), [5] a class of compounds with a broad range of important biological applications. [6,7] Our group demonstrated recently that [(salen)Al] complexes efficiently catalyze the highly enantioselective conjugate addition of HN 3 , [8a,e] HCN, [8b] electron-deficient nitrile derivatives, [8c,e] and oximes [8d] to a,b-unsaturated imides and ketones in the absence of added base. As each of these nucleophiles includes a relatively acidic X À H (X = N, C, O) bond (pK a 5-17), we hypothesized that heterocyclic compounds bearing similarly acidic NÀH bonds might be suitable reaction partners in [(salen)Al]-catalyzed conjugate additions. Herein, we report the successful development of catalytic asymmetric conjugate additions of aromatic N-heterocycles to a,b-unsaturated carbonyl compounds. Both a,b-unsaturated imides and ketones undergo efficient and highly regio-and enantioselective additions with a variety of both fused and nonfused aromatic heterocyclic compounds. This methodology introduces a new, versatile synthetic method for the preparation of interesting chiral building blocks, including NNNs.Purine, the structural core of the nucleobases in the most promising antiviral agents, [7a] was chosen as a model substrate. It contains a relatively acidic NÀH bond (pK a 8.6) and is known to exist in two (N7-H and N9-H) tautomeric forms.[9a]The oxo-bridged dimeric catalyst 1[8c] was found to promote the addition of purine to 3-hepten-2-one (2 b) in the absence of external base. The reaction resulted in full conversion into

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Aluminum chloride complexes with purine, adenine and guanine

Cited by 27 publications

References 43 publications

Interaction of carbonylchlorohydridotris (triphenylphosphine) ruthenium (II) with purine, adenine, cytosine and cytidine

Interaction of carbonylchlorohydridotris (triphenylphosphine) ruthenium (II) with purine, adenine, cytosine and cytidine

Aluminium polyphosphate in the ectomycorrhizal fungus Suillus variegatus (Fr.) O. Kunze as revealed by energy dispersive spectrometry

Highly Enantioselective Catalytic Conjugate Addition of N‐Heterocycles to α,β‐Unsaturated Ketones and Imides

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