Conformational transmission in pentacoordinated phosphorus systems, modelling the activated state of cyclic AMP

The first successful crystal structures of biorelevant nucleoside and carbohydrate-based phosphoranes are reported. Employing thymidine, a nucleotidyl phosphorane was synthesized in 90% yield and was shown by X-ray analysis to possess a trigonal bipyramidal geometry. With the use of 1,2-O-isopropylidene-alpha-d-glucofuranose, a carbohydrate-based phosphorane was formed and similarly found to have a trigonal bipyramidal geometry. NMR studies demonstrated the existence of isomerism in solution associated with the nucleotidyl phosphorane and rapid exchange for the carbohydrate-based phosphorane. The geometrical representations reported here are expected to have significant applications associated with active site mechanisms of phosphoryl transfer enzymes, for example, in DNA, RNA, c-AMP, and others.

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Biologically Relevant Phosphoranes: Structural Characterization of a Nucleotidyl Phosphorane

Timosheva

Chandrasekaran

Holmes

2005

J. Am. Chem. Soc.

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The Chemical and Biochemical Properties of Methylphosphotriester DNA

Buck¹

2004

Nucleosides, Nucleotides and Nucleic Acids

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Conformational transmission in pentacoordinated phosphorus systems, modelling the activated state of cyclic AMP

Abstract: The proposed activated state of cyclic adenosine 3 ',

Cited by 2 publications

References 48 publications

Biologically Relevant Phosphoranes: Structural Characterization of a Nucleotidyl Phosphorane

Biologically Relevant Phosphoranes: Structural Characterization of a Nucleotidyl Phosphorane

The Chemical and Biochemical Properties of Methylphosphotriester DNA

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