Nucleoside phosphate analogues of biological interest, and their synthesis via aryl nucleoside H-phosphonates as intermediates.

• Authors: Jacek Cieślak , Michał Sobkowski , Jadwiga Jankowska , Małgorzata Wenska , Marzena Szymczak , Barbara Imiołczyk , Izabela Zagórowska , David Shugar , Jacek Stawiński , Adam Kraszewski
• Languages of publication: EN

Abstracts

EN

This review presents a brief account of the chemistry and mechanistic aspects of aryl H-phosphonates, and selected applications of this class of compounds as intermediates in the synthesis of a wide range of biologically important analogues of nucleoside phosphates, and oligonucleotides, in which the phosphate moieties are replaced by other structurally related groups. The aryl nucleoside H-phosphonates, compounds of controlled reactivity, have proven to be more versatile and superior to various mixed anhydrides as synthetic intermediates, particularly for preparation of nucleotide analogues bearing P-N or P-S bonds in various configurational arrangements at the phosphate moiety.

Keywords

EN

H-phosphono(di)thioates; aryl nucleoside H-phosphonates; nucleoside 2',3'-cyclic phosphate analogues; H-phosphonamidates; nucleophilic catalysis

• Publisher: Polish Biochemical Society
• Journal: Acta Biochimica Polonica
• Year: 2001
• Volume: 48
• Issue: 2
• Pages: 429-442

Dates

published

2001

received

2001-02-14

revised

2001-05-22

accepted

2001-05-31

Contributors

author

Jacek Cieślak

• Institute of Bioorganic Chemistry, Polish Academy of Sciences, Z. Noskowskiego 12/14, 61-704 Poznań, Poland

author

Michał Sobkowski

• Institute of Bioorganic Chemistry, Polish Academy of Sciences, Z. Noskowskiego 12/14, 61-704 Poznań, Poland

author

Jadwiga Jankowska

• Institute of Bioorganic Chemistry, Polish Academy of Sciences, Z. Noskowskiego 12/14, 61-704 Poznań, Poland

author

Małgorzata Wenska

• Institute of Bioorganic Chemistry, Polish Academy of Sciences, Z. Noskowskiego 12/14, 61-704 Poznań, Poland

author

Marzena Szymczak

• Institute of Bioorganic Chemistry, Polish Academy of Sciences, Z. Noskowskiego 12/14, 61-704 Poznań, Poland

author

Barbara Imiołczyk

• Institute of Bioorganic Chemistry, Polish Academy of Sciences, Z. Noskowskiego 12/14, 61-704 Poznań, Poland

author

Izabela Zagórowska

• Institute of Bioorganic Chemistry, Polish Academy of Sciences, Z. Noskowskiego 12/14, 61-704 Poznań, Poland

author

David Shugar

• Institute of Biochemistry and Biophysics, Polish Academy of Sciences, Warszawa, Poland

author

Jacek Stawiński

• Institute of Bioorganic Chemistry, Polish Academy of Sciences, Z. Noskowskiego 12/14, 61-704 Poznań, Poland

author

Adam Kraszewski

• Institute of Bioorganic Chemistry, Polish Academy of Sciences, Z. Noskowskiego 12/14, 61-704 Poznań, Poland

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