Nucleoside phosphonic acids. V. Inhibition of micrococcal nuclease with 5'-deoxythymidine-5'-phosphonic acid containing oligomers

Dh, Rammler; Bagdasarian, Andranik; Morris, Frank X.

doi:10.1021/bi00751a002

Cited by 7 publications

References 9 publications

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Synthesis of 2′,5′‐Dideoxyuridine‐5′‐phosphonates

Aly¹,

Abdel-Megied²,

Pedersen³

et al. 1992

Liebigs Ann. Chem.

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Methyl 2,5-dideoxy-5-iodo-3-O-pivaloyl-~-erythro-pentofuranoside (5) was synthesized from 2-deoxy-~-ribose and treated with triethyl phosphite to give the phosphonate 6. Reaction of 6 with silylated 2,4-dihydroxypyrimidine 7 in the presence of trimethylsilyl trifluoromethanesulfonate as catalyst afforded nucleoside phosphonates 8 and 9 which were deprotected with C2H,0Na in ethanol to give the diethyl 2',5'-dideoxyuridine-5'-phosphonate 10 and its a-anomer 11. No activity was found for the nucleosides 8-11 against HIV or HSV-1. hitherto have been prepared from the corresponding natural nucleoside, one can assume that other nucleoside derivatives can be similarly prepared. However, there is a need for a more convenient route, especially, for nucleoside 5'-phosphonates with unnatural nucleobases. It would be of interest to avoid the synthesis of the nucleoside prior to the synthesis of the phosphonate. In this paper we describe the coupling of an adequately substituted 2,5-dideoxy sugar 5-phosphonate with silylated uracil as an example of a convergent synthesis of such compounds.

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Synthesis of 2′,5′‐Dideoxyuridine‐5′‐phosphonates

Aly¹,

Abdel-Megied²,

Pedersen³

et al. 1992

Liebigs Ann. Chem.

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Staphylococcal nuclease reviewed: A prototypic study in contemporary enzymology. I isolation; physical and enzymatic properties

1978

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This is the first of a series of four articles in which the chemical, enzymological, and crystallographic work on Ribonucleate (deoxyribonucleate)-3'-nucleotidohydrolase, EC 3.1.4.7, (Staphylococcal nuclease, Micrococcal nuclease) will be reviewed and correlated. This article discusses the purification of the enzyme and its general physical and enzymological properties. Subsequent articles will deal with specific studies of the nucleotide binding site, crystallographic studies of a nuclease-inhibitor complex, use of the nuclease as a model for protein folding and possible mechanisms for the action of the enzyme.

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The binding of dinucleoside phosphonates in the active site of the metallo-enzyme, Staphylococcal nuclease: synthetic, solution and preliminary crystallographic studies

Tucker

Edge

Jones

et al. 1995

Inorganica Chimica Acta

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Nucleoside phosphonic acids. V. Inhibition of micrococcal nuclease with 5'-deoxythymidine-5'-phosphonic acid containing oligomers

Abstract: This is paper V in a series entitled "Nucleoside Phosphonic Acids." For previous papers in series, see Rammler and Bax (1970).

Cited by 7 publications

References 9 publications

Synthesis of 2′,5′‐Dideoxyuridine‐5′‐phosphonates

Synthesis of 2′,5′‐Dideoxyuridine‐5′‐phosphonates

Staphylococcal nuclease reviewed: A prototypic study in contemporary enzymology. I isolation; physical and enzymatic properties

The binding of dinucleoside phosphonates in the active site of the metallo-enzyme, Staphylococcal nuclease: synthetic, solution and preliminary crystallographic studies

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