Catalytic cleavage of phosphate ester bonds by boron chelates

Details Catalytic cleavage of phosphate ester bonds by boron chelates Catalytic cleavage of phosphate ester bonds by boron chelates

2007-01-23

2007-01-23

Solola, Taofiq (Department: 1626)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Heterocyclic carbon compounds containing a hetero ring...

C544S069000, C549S004000

Reexamination Certificate

active

10774619

ABSTRACT:
Novel chemical compounds are disclosed having the general formula L{YXm}n, wherein X is selected from the Group 13 elements, Y is a halide, and L is a chelating ligand containing at least one binding atom contacting the Group 13 element, the atom being selected from the group consisting of C, N, O, and S, and m and n are integers having a value of at least 1. L may be a Schiff base type ligand, such as a salen ligand. The compositions of the present invention may be bidentate, quadridentate, or greater. The compositions may be used in dealkylation of phosphate esters or ethers. Advantageously, the methods of the present invention may be rendered catalytic.

REFERENCES:
Keizer et al., Canadian J. Chem, (2002), vol. 80, No. 11, p. 1463-68.
David et al. Accelerated hydrolysis of industrial organophosphates in water and soil using sodium perborate. Environmental Pollution. vol. 105. 1999. pp. 121-128.
Wei et al. Chelated Borates: Synthesis, reactivity, and cation formation. Inorg. Chem. vol. 37. 1998. pp. 4934-4938.
Wei et al. Synthesis and Structures of Salen-Supported Borates Containing Siloxides. Inorg. Chem. vol. 38. 1999. pp. 3914-3918.
Brown et al. An intramolecularly Stabilized Arylboron Dibromide. Heteroatom Chemistry. vol. 9. No. 1. 1998. pp. 79-83.
Yang et al. Chemical detoxification of Nerve Agent VX. Acc. Chem. Res. vol. 32. 1999. pp. 109-115.
Blasko et al. Recent Studies of Nucleophilic General-Acid, and Metal Ion Catalysis of Phosphate Diester Hydrolysis. Acc. Chem. res. vol. 32. 1999. pp. 475-484.
Oivanen et al. Kinetics and Mechanisms for the cleavage and Isomerization of the Phosphodiester bonds of RNA by bronsted acids and Bases. Chem. Rev. vol. 87. 1998. pp. 961-990.
Gajda et al. Highly efficient phosphodiester hydrolysis promoted by dinuclear copper (II) complex. Inorg. Chem. vol. 40. 2001. pp. 4918-4927.
Jones et al. Enhanced base hydrolysis of coordinated phosphate esters: the reactivity of an unusual cobalt (III) amine dimer. J. Am. Chem. Soc. 1984. vol. 106. pp. 7807-7819.
Vance et al. Functional group convergency in a binuclear dephosphorylation reagent. J. Ame. Chem. Soc. vol. 115. 1993. pp. 12165-12166.
McCue et al. Hydrolysis of a model for the 5′-cap pf mRNA by dinuclear copper (II) and Zinc (II) Complexes. Rapid hydrolysis by four copper (II) ions. Inorg. Chem. vol. 38. 1999. pp. 6136-6142.
Scrimin et al. Comparative reactivities of phosphate ester cleavages by metallomicelles. Langmuir. vol. 12. 1996. pp. 6235-6241.
Yamami et al. Macrocyclic heterodinuclear ZnIIPbII complexes: synthesis, structures, and hydrolytic function toward Tris (p-nitrophenyl) phosphate. Inorg. Chem. 1998. vol. 37. pp. 6832-6838.
Kaminskaia et al. Reactivity of u-hydroxodizinc (II) centers in enzymatic catalysis through model studies. Inorg. Chem. vol. 39. 2000. pp. 3365-3373.
Chapman et al. Selective hydrolysis of phosphate esters, nitrophenyl phosphates and UpU, by dimetric zinc complexes depends on the spacer length. J. Ame. Chem. Soc. 1995. vol. 117. pp. 5462-5469.
Molenveld et al. Highly efficient phosphate diester transesterification by a Calix [4] arene-based dinuclear zinc (II) catalyst. J. Am. Chem. Soc. vol. 119. 1997. pp. 2948-2949.
Benton et al. The cleavage of ethers with boron bromide. I. Some common ether. J. Am/ Chem. Soc. vol. 64. 1942. pp. 1128-1129.
Kim et al. Direct conversion of silyl ethers into alkyl bromides with boron tribromide. J. Org. Chem. vol. 53. 1988. pp. 3111-3113.
Bazzicalupi et al. Carboxy and diphosphate ester hydrolysis by a dizinc complex with a new alcohol-pendant macrocycle. Inorg. Chem. 1999. vol. 38. pp. 4115-4122.
Ember Lois. EPA Destroying chemical arms:No easy task. C & EN. Aug. 30, 1999. pp. 11-12.
Ranu et al. Dealkylation of ethers. A review. Organic preparations and procedures int. vol. 28. No. 4. pp. 371-409.
Miguel-Angel Munoz-Hernandez et al., “Reactivity and Derivitization of Five-Coordinate, Chelated Aluminum,” Inorg. Chem, 2001, 40, 6782-6787.
Y. Wang et al., “Ligand-Tetrahydrofuran Coupling in Chelated Aluminum Phosphinates,” Inorg. Chem. 2002, 41, 558-565.
Yuzhong Wang et al., “Five-Coordinate Organoaluminum Acetylides and Crystal Structure of the Hydrosylate, [Salophen (tBu)Al]2O,” Journal of Organometallic Chemistry 689 (2004). 759-765.
David, Michael D. et al., Accelerated hydrolysis of industrial organophosphates in water and soil using sodium perborate; Environ. Pollution 105 (1999) 121-128.
Olivanen, Mikko et al., Kinetics and Mechanisms for the Cleavage and Isomerization of the Phosphodiester Bonds of RNA by Bronsted Acids and Bases; Chem. Rev. 1998, 98, 961-990.
Blasko, Andrei et al., Recent Studies of Nucleophilic, General-Acid, and Metal Ion Catalysis of Phosphate Diester Hydrolysis; Acc. Chem. Res. 1999, 32, 475-484.
Bazzicalupi, Carla et al., Carboxy and Diphosphate Ester Hydrolysis by a Dizinc Complex with a New Alcohol-Pendant Macrocycle; Inorg. Chem. 1999, 38, 4115-4122.
Gajda, Tamas et al., Highly Efficient Phosphodiester Hydrolysis Promoted by a Dinuclear Copper (II) Complex; Inorg. Chem., 2001, 40, 4918-4927.
Jones, David R. et al., Enhanced Base Hydrolysis of Coordinated Phosphate Esters: The Reactivity of an Unusual Cobalt (III) Amine Dimer; J. Am. Chem. Soc. 1984, 106, 7807-7819.
Vance, David H. et al., Functional Group Convergency in a Binuclear Dephosphorylation Reagent; J. Am. Chem. Soc., 1993, 115, 12165-12166.
McCue, Kevin P. et al., Hydrolysis of a Model for the 5′-Cap of mRNA by Dinuclear Copper (II) and Zinc (II) Complexes . . . Rapid Hydrolysis by Four Copper (II) Ions; Inorg. Chem. 1999, 38, 6136-6142.
Scrimin, Paolo et al., Comparative Reactivities of Phosphate Ester Cleavages by Metallomicelles, Langmuir 1996, 12, 6235-6241.
Kaminskaia, Natalia V., et al., Reactivity of u-Hydroxodizinc (II) Centers in Enzymatic Catalysts through Model Studies; Inorg. Chem. 2000, 39, 3365-3373.
Yamami, Masako et al., Macrocyclic Heterodinuclear ZnIIPbII Complexes: Synthesis, Structures and Hydrolytic Function toward Tris(p-nitrophenyl) Phosphate; Inorg. Chem. 1998, 37, 6832-6838.
Chapman, William H. Jr. et al., Selective Hydrolysis of Phosphate Esters, Nitrophenyl Phosphates and UpU, by Dimeric Zinc Complexes Depends on the Spacer Length; J. Am. Chem. Soc. 1995, 117, 5462-5469.
Molenveld, Peter et al., Highly Efficient Phosphate Diester Transesterification by a Calix[4]arene-Based Dinuclear Zinc(II) Catalyst;J. Am. Chem. Soc. 1997, 119, 2948-2949.
Benton, F.L. et al., The Cleavage of Ethers with Boron Bromide; Contrib. from Chemical Labs of U. of Notre Dame, May 1942; vol. 64 p. 1128.
Kim, Sunggak et al., Direct Conversion of Silyl Ethers into Alkyl Bromides with Boron Tribromide, J. Org. Chem. 1988, 53, 3111-3113.
Wei, Pingrong et al., Synthesis and Structure of Salen-Supported Borates Containing Siloxides, Inorg. Chem. 1999, 38, 3914-3918.
Brown, David S., An Intramolecularly Stabilized Arylboron Dibromide, Heteroatom Chem. vol. 9, No. 1, 1998, 79-83.
Yang, Yu-Chu, Chemical Detoxification of Nerve Agent VX, Acc. Chem. Res. 1999, 32, 109-115.
Ember, Lois, Destroying chemical arms: No easy task, C&EN Aug. 30, 1999, 11.
Hileman, bette, EPA Cuts Use of Common Pesticide, C&EN Jun. 12, 2000, 11.
Goodman, Steven N. et al., A Practical Synthesis of a,B-Unsaturated Imides, Useful Substrates For Asymmetric Conjugate Addition Reactions, Adv. Synth. Catal. 2002, 344, No. 9.

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