Tomas Szabó

Nucleoside Phosphonates. Development of Synthetic Methods and Reagents

Abstract In this paper a short account of our recent research concerning development of new synthetic methods and new reagents for the preparation of DNA and RNA fragments and their analogues is given. #Dedicated to Professor Yoshihisa Mizuno on the occasion of his 75th birthday. ¶Present address: Astra Production Chemicals, S-151 85 Sodertalje, Sweden.

Synthesis and some conformational features of the 5′-deoxy-5′-methylphosphonate linked dimer, 5′-deoxy-5′-C-(phosphonomethyl)thymidin-3′-yl (thymidin-5′-yl)methylphosphonate [p(ch2Tp(ch2T]

Abstract Efficient synthesis of the 5′-deoxy-5′-methylphosphonate linked thymidine dimer 11 [p( ch 2 Tp( ch 2 T] was developed via the 5′-deoxy-5′-C-(phosphonomethyl)-3′-silylated thymidine derivative 4 as a key intermediate. Conformational analysis of the sugar parts of the dimer showed that the deoxyribose residues exist in solution mainly in the S-type conformations but with a predominant contribution of antiperiplanar rotamers around the C4′ – C5′ bonds in both sugar units.

A new approach to stereospecific synthesis of P-chiral phosphorothioates. Preparation of diastereomeric dithymidyl-(3?-5?) phosphorothioatesElectronic supplementary information (ESI) available: synthesis and characterization of compounds 2 through 6. See http://www.rsc.org/suppdata/cc/b3/b311912b/

A new method for stereospecific synthesis of P-chiral phosphorothioates based on intramolecular nucleophile catalysis was developed.

Preparation of nucleoside 5′-deoxy-5′-methylenephosphonates as building blocks for the synthesis of methylenephosphonate analogues

Efficient synthesis of suitably protected 2′-deoxycytidine, 2′-deoxyadenosine, and 2′-deoxyguanosine derivatives bearing the 5′-methylenephosphonate moiety with the 4-methoxy-1-oxido-2-picolyl function as an intramolecular nucleophile catalytic group is described.

Solid Phase Synthesis of 5′-Methylenephosphonate DNA

Abstract A new approach to the solid phase synthesis of 5′-methylenephosphonate DNA is described. It makes use of intramolecular catalysis which ensures rapid and high-yielding condensations and thus provides a convenient entry to ionic, achiral analogs of thymidylic acids up to 20 nucleotides in length.

Recent Studies in Nucleoside Phosphonate Chemistry

Abstract New activation pathways have been found for H-phosphonate monoesters subjected to a reaction with alkyl chlorophosphates or sterically hindered aromatic acyl chlorides. Studies on synthesis of nucleoside methylphosphnate diesters using a new condensing system are also discussed.

Studies on Nucleoside Phosphonates and Their Derivatives. a Progress Report

Abstract Abstract: Some synthetic, mechanistic and structural aspects of ongoing research on biologically important phosphate derivatives and their analogues are discussed.