Rapid Hydrolysis of 2‘,3‘-cAMP with a Cu(II) Complex:  Effect of Intramolecular Hydrogen Bonding on the Basicity and Reactivity of a Metal-Bound Hydroxide

Wall, Mark; Linkletter, Barry A.; Williams, Dan; Lebuis, Anne‐Marie; Hynes, Rosemary C.; Chin, Jik

doi:10.1021/ja981227l

Cited by 107 publications

(86 citation statements)

References 11 publications

(14 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…(Wang et al, 1996;Wall et al, 1999;Naing et al, 1995). Some Co(II)-phenanthroline complexes have been synthesized and structures were determined (Ding et al, 2006;Xuan & Zhao, 2007;Zhao et al, 2008).…”

Section: Methodsmentioning

confidence: 99%

See 1 more Smart Citation

Aqua(dicyanamido-κN¹)(2,9-dimethyl-1,10-phenanthroline-κ²N,N′)(nitrato-κ²O,O′)cobalt(II)–2,9-dimethyl-1,10-phenanthroline–water (2/1/2)

Fenghua

Zhao

2011

Acta Cryst E

View full text Add to dashboard Cite

2 O, the Co II ion is coordinated by a bidentate 2,9-dimethyl-1,10-phenanthroline (dmphen) ligand, a bidentate nitrate anion, a water molecule and a monodentate dicyanamide group in a distorted octahedral geometry. One uncoordinated dmphen molecule is situated on a crystallographic twofold axis and the asymmetric unit is completed by one water molecule. In the crystal, molecules form a onedimensional framework in the [001] direction through O-HÁ Á ÁN and O-HÁ Á ÁO hydrogen bonds. The crystal packing is further stabilized by -stacking interactions between the dmphen rings of neighboring molecules, with a centroidcentroid separation of 3.5641 (8) Å and a partially overlapped arrangement of parallel dmphen rings with a distance of 3.407 (2) Å . Related literature

show abstract

Section: Methodsmentioning

confidence: 99%

“…For background to metal-phenanthroline complexes, see: Naing et al (1995); Wang et al (1996); Wall et al (1999). For related Co(II)-phenanthroline structures, see: Ding et al (2006); Xuan & Zhao (2007); Zhao et al (2008).…”

Section: Related Literaturementioning

confidence: 99%

Aqua(dicyanamido-κN¹)(2,9-dimethyl-1,10-phenanthroline-κ²N,N′)(nitrato-κ²O,O′)cobalt(II)–2,9-dimethyl-1,10-phenanthroline–water (2/1/2)

Fenghua

Zhao

2011

Acta Cryst E

View full text Add to dashboard Cite

show abstract

“…For the features of metal-phenanthroline complexes, see: Naing et al (1995); Wang et al (1996); Wall et al (1999). For related structures, see : Cheng et al (2007); Xuan et al (2007); Zhao et al (2007).…”

Section: Related Literaturementioning

confidence: 99%

“…Metal-phenanthroline complexes have attracted much attention because of their peculiar features (Wang et al, 1996;Wall et al, 1999;Naing et al, 1995). Some Cu(II)-phenanthroline complexes have been synthesized and structures were determined (Cheng et al, 2007;Xuan et al, 2007;Zhao et al, 2007).…”

Section: S1 Commentmentioning

confidence: 99%

(2,9-Dimethyl-1,10-phenanthroline-κ²N,N′)bis(2-hydroxybenzoato-κO)copper(II)

2008

View full text Add to dashboard Cite

Key indicators: single-crystal X-ray study; T = 291 K; mean (C-C) = 0.006 Å; R factor = 0.045; wR factor = 0.121; data-to-parameter ratio = 13.2.The Cu II atoms in the two independent molecules of the title compound, [Cu(C 7 H 5 O 3 ) 2 (C 14 H 12 N 2 )], are each coordinated by a bidentate 2,9-dimethyl-1,10-phenanthroline (dmphen) molecule and two monodentate 2-hydroxybenzoate anions in a distorted tetrahedral geometry. The crystal packing is stabilized by intramolecular hydrogen bonding andinteractions between the dmphen rings of neighboring molecules, with distances between their ring planes of 3.5670 (4) and 3.5181 (9) Å . Related literature

show abstract

“…However, for the other complexes with the same protons in the L-ATP and Zn(II)-L-ATP systems, due to the high protonation degree of the anionic substrate, the interaction in the ternary systems is weaker although the corresponding receptors have the same charge (except for complex ZnLATPH 2 ). In the Zn(II)-L-ATP systems, besides the coordinationbound, bridged p-p stacking interactions between the phen and the adenosine of nucleotide ( 1 H NMR), ion-pairing and H-bonding interactions ( 31 P NMR) (Lehn, 1988;Bianchi et al, 2000;Mitchell and Sigel, 1978;Wall et al, 1999), as shown in Scheme 2, there probably exist other types of interactions, involving ion-p-donor (Siu et al 2001), hydrophobic/hydrophilic (phen and nucleoside residue/ amino nitrogen and phosphate oxygen atoms), and even van der Waals interactions. Thus, the self-assembly of the Zn(II)/L/ATP system is similar to that occurring in the biosystem.…”

Section: Zn(ii) Complexes Of L Recognize Atpmentioning

confidence: 99%

Recognition promoted by Zn²⁺ between phenanthroline bridging polyaza ligands and nucleotides — Zn²⁺ acts as ‘messenger’ between the receptor and substrate

Guo

Lin

et al. 2003

J of Molecular Recognition

View full text Add to dashboard Cite

The stability constants of the supramolecular complexes formed between L ((a,b,c,d)) or their Zn(2+) complexes, and adenosine 5'-triphosphate (ATP) in aqueous solution were determined by potentiometric titrations (25 degrees C, I = 0.1 mol dm(-3) KNO(3)). The results show that protonated aliphatic-substituted L (a,d) and aromatic-substituted L (b,c) ligands and/or Zn(II) ion can efficiently recognition the substrate, ATP. All of the equilibrium studies, (1)H and (31)P nuclear magnetic resonance spectra indicate that multiple interactions, including coordination, pi-stacking, ion-pairing, H-bonding, and possible ion-pi-donor, hydrophobic and even van der Waals interactions exist in the Zn(II)-L-ATP systems. On the other hand, the recognition of the substrates by the protonated ligands was significantly promoted by the addition of Zn(II), which leads to coordination competition between the mixed ligands, L and nucleotide. In Zn(II)/L/ATP systems the tendency for phosphate chain to receive proton and metal ion increases, facilitating the cleavage of the phosphate chain of the nucleotide.

show abstract

Rapid Hydrolysis of 2‘,3‘-cAMP with a Cu(II) Complex: Effect of Intramolecular Hydrogen Bonding on the Basicity and Reactivity of a Metal-Bound Hydroxide

Cited by 107 publications

References 11 publications

Aqua(dicyanamido-κN¹)(2,9-dimethyl-1,10-phenanthroline-κ²N,N′)(nitrato-κ²O,O′)cobalt(II)–2,9-dimethyl-1,10-phenanthroline–water (2/1/2)

Aqua(dicyanamido-κN¹)(2,9-dimethyl-1,10-phenanthroline-κ²N,N′)(nitrato-κ²O,O′)cobalt(II)–2,9-dimethyl-1,10-phenanthroline–water (2/1/2)

(2,9-Dimethyl-1,10-phenanthroline-κ²N,N′)bis(2-hydroxybenzoato-κO)copper(II)

Recognition promoted by Zn²⁺ between phenanthroline bridging polyaza ligands and nucleotides — Zn²⁺ acts as ‘messenger’ between the receptor and substrate

Contact Info

Product

Resources

About

Rapid Hydrolysis of 2‘,3‘-cAMP with a Cu(II) Complex: Effect of Intramolecular Hydrogen Bonding on the Basicity and Reactivity of a Metal-Bound Hydroxide

Cited by 107 publications

References 11 publications

Aqua(dicyanamido-κN1)(2,9-dimethyl-1,10-phenanthroline-κ2N,N′)(nitrato-κ2O,O′)cobalt(II)–2,9-dimethyl-1,10-phenanthroline–water (2/1/2)

Aqua(dicyanamido-κN1)(2,9-dimethyl-1,10-phenanthroline-κ2N,N′)(nitrato-κ2O,O′)cobalt(II)–2,9-dimethyl-1,10-phenanthroline–water (2/1/2)

(2,9-Dimethyl-1,10-phenanthroline-κ2N,N′)bis(2-hydroxybenzoato-κO)copper(II)

Recognition promoted by Zn2+ between phenanthroline bridging polyaza ligands and nucleotides — Zn2+ acts as ‘messenger’ between the receptor and substrate

Contact Info

Product

Resources

About

Aqua(dicyanamido-κN¹)(2,9-dimethyl-1,10-phenanthroline-κ²N,N′)(nitrato-κ²O,O′)cobalt(II)–2,9-dimethyl-1,10-phenanthroline–water (2/1/2)

Aqua(dicyanamido-κN¹)(2,9-dimethyl-1,10-phenanthroline-κ²N,N′)(nitrato-κ²O,O′)cobalt(II)–2,9-dimethyl-1,10-phenanthroline–water (2/1/2)

(2,9-Dimethyl-1,10-phenanthroline-κ²N,N′)bis(2-hydroxybenzoato-κO)copper(II)

Recognition promoted by Zn²⁺ between phenanthroline bridging polyaza ligands and nucleotides — Zn²⁺ acts as ‘messenger’ between the receptor and substrate