ChemInform Abstract: Adenosine 5′‐(α,β‐Imido)triphosphate, a Substrate for T7 RNA Polymerase and Rabbit Muscle Creatine Kinase.

Ma, Qi-Feng; Babbitt, Patricia C.; Kenyon, George L.

doi:10.1002/chin.198839305

Cited by 3 publications

(5 citation statements)

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“…2′-Methoxyadenosine was prepared from adenosine, by reaction with methyl iodide under alkaline conditions as previously described44. Adenosine 5′- O - α,β ,-imidodiphosphate (AMPNP) was synthesized by reaction of 5′-tosyladenosine45 with imidodiphosphate salt45, 46. Adenosine 5′- O - α,β -difluoromethylenediphosphate (ADPβF) was prepared by coupling 5′-tosyladenosine to difluoro substituted methylenediphosphonic acid, as previously reported45, 47.…”

Section: Methodsmentioning

confidence: 99%

“…2′-Methoxyadenosine was prepared from adenosine by reaction with methyl iodide under alkaline conditions as previously described . Adenosine-5′- O -α,β,-imidodiphosphate (AMPNP) was synthesized by reaction of 5′-tosyladenosine with imidodiphosphate salt. , Adenosine-5′- O -α,β-difluoromethylenediphosphate (AMPCF 2 P) was prepared by coupling 5′-tosyladenosine to difluoro substituted methylenediphosphonic acid, as previously reported. , Adenosine-5′- O -thiophosphosulfate (APSαS) was synthesized by reacting pyridine- N -sulfonic acid with adenosine-5′- O -thiopshophate (AMPS), as previously described . Structures and purity (≥95%) were confirmed by 1 H, 31 P NMR, and HPLC analysis (data not shown).…”

Section: Methodsmentioning

confidence: 99%

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Identification of Critical Ligand Binding Determinants in Mycobacterium tuberculosis Adenosine-5′-phosphosulfate Reductase

Hong¹,

Bhave²,

Carroll

2009

J. Med. Chem.

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Mycobacterium tuberculosis adenosine 5′-phosphosulfate (APS) reductase is an iron-sulfur protein and a validated target to develop new anti-tubercular agents, particularly for the treatment of latent infection. To facilitate the development of potent and specific inhibitors of APS reductase, we have probed the molecular determinants that underlie binding and specificity through a series of substrate and product analogs. Our study highlights the importance of specific substitutent groups for substrate binding and provides functional evidence for ligand-specific conformational states. An active site model has been developed for M. tuberculosis APS reductase that is in accord with the results presented here as well as prior structural data reported for Pseudomonas aeruginosa APS reductase and related enzymes. This model illustrates the functional features required for the interaction of APS reductase with a ligand and provides a pharmacological road map for the rational design of small-molecules as potential inhibitors of APS reductase present in human pathogens, including M. tuberculosis.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Identification of Critical Ligand Binding Determinants in Mycobacterium tuberculosis Adenosine-5′-phosphosulfate Reductase

Hong¹,

Bhave²,

Carroll

2009

J. Med. Chem.

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“…On a larger scale, removal of the excess inorganic phosphate becomes a significant issue. The same chemistry, with noncleavable phosphate linkages (such as CH 2 ), has been validated and appears to be more general (Scheme ).…”

Section: Atp Analogues and Their Interactions With Protein Kinasesmentioning

confidence: 98%

Using Chemical Genetics and ATP Analogues To Dissect Protein Kinase Function

et al. 2007

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Protein kinases catalyze the transfer of the gamma-phosphate of ATP to a protein substrate and thereby profoundly alter the properties of the phosphorylated protein. The identification of the substrates of protein kinases has proven to be a very difficult task because of the multitude of structurally related protein kinases present in cells, their apparent redundancy of function, and the lack of absolute specificity of small-molecule inhibitors. Here, we review approaches that utilize chemical genetics to determine the functions and substrates of protein kinases, focusing on the design of ATP analogues and protein kinase binding site mutants.

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“…The nucleoside-α,β-imidodiphosphate is chemically synthesized and then enzymatically phosphorylated. Displacement of the tosylate leaving group in adenosine 5′-tosylate S.112 by tris(tetrabutylammonium) imidodiphosphate gives access to adenosineα,β-imidodiphosphate S.113 (Ma et al, 1988).…”

Section: Overview Of the Synthesis Of Nucleoside Phosphates And Polypmentioning

confidence: 99%

“…The nucleoside‐α,β‐imidodiphosphate is chemically synthesized and then enzymatically phosphorylated. Displacement of the tosylate leaving group in adenosine 5′‐tosylate S.112 by tris(tetrabutylammonium) imidodiphosphate gives access to adenosine‐α,β‐imidodiphosphate S.113 (Ma et al, ). Enzymatic phosphorylation of S.113 by creatine kinase using phosphoenol pyruvate as the phosphoryl donor provides access to APNPP ( S.114 ).…”

Section: Nucleotide Analogsmentioning

confidence: 99%

Overview of the Synthesis of Nucleoside Phosphates and Polyphosphates

Johnson

Widlanski

2003

CP Nucleic Acid Chemistry

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This overview summarizes methodology used for the synthesis of nucleoside mono-, di-, and triphosphates. Selected techniques such as the Mitsunobu reaction, displacement reactions involving nucleoside 5'-tosylates, "anion-exchange" techniques, and phosphoramidite and phosphoramidate methodologies are highlighted. The chemistry of phosphorylation is detailed with respect to advantages and limitations under various conditions. Applicability of the methods toward the synthesis of analogs such as imidophosphates, phosphorothioates, and radiolabeled nucleotides is also addressed.

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ChemInform Abstract: Adenosine 5′‐(α,β‐Imido)triphosphate, a Substrate for T7 RNA Polymerase and Rabbit Muscle Creatine Kinase.

Cited by 3 publications

References 1 publication

Identification of Critical Ligand Binding Determinants in Mycobacterium tuberculosis Adenosine-5′-phosphosulfate Reductase

Identification of Critical Ligand Binding Determinants in Mycobacterium tuberculosis Adenosine-5′-phosphosulfate Reductase

Using Chemical Genetics and ATP Analogues To Dissect Protein Kinase Function

Overview of the Synthesis of Nucleoside Phosphates and Polyphosphates

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