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Oxidative Cleavage of Ribofuranose 5-(α-Hydroxyphosphonates): a Route to Erythrofuranose-based Nucleoside Phosphonic Acids by Šárka Králíková; Miloš Buděšínský; Ivana Tomečková; Ivan Rosenberg is a Chemistry article available to read on EtoBox.

What is Oxidative Cleavage of Ribofuranose 5-(α-Hydroxyphosphonates): a Route to Erythrofuranose-based Nucleoside Phosphonic Acids about?

We report here an oxidative cleavage of (5R)-and (5S)-ribofuranosyl-5-C-phosphonate derivatives with periodate anion under both strong acidic and neutral conditions. In both cases, only (5R)-configured compound underwent the expected oxidation reaction and afforded the desired (4R)-erythrofuranosylphosphonate, whereas the second epimer, (5S)-ribofuranosyl-5-C-phosphonate did not provide the corresponding (4S)-erythrofuranosylphosphonate derivative. This different behavior of epimers toward oxidative cleavage is an important phenomenon. The obtained (4R)-erythrofuranosylphosphonate was used for the preparation of phosphonate mimic of adenosine 5 0 -phosphate via classical nucleosidation reaction. Condensation of the protected shortened AMP analogue with adenosine derivatives, however, provided only the 2 0 ,5 0 -linked ApA analogue. Study on hybridization of the modified 2 0 -5 0 ApAwith polyU revealed its ability to form stable triplex-like complex, similar to natural 2 0 -5 0 r(ApA) and 3 0 -5 0 r(ApA). NMR spectroscopy study showed that the erythrofuranose part of the phosphonate nucleotide unit of modified 2 0 -5 0 ApA was predominantly in the C2 0 -endo conformation, which is c

Who reads Oxidative Cleavage of Ribofuranose 5-(α-Hydroxyphosphonates): a Route to Erythrofuranose-based Nucleoside Phosphonic Acids?

Author

Šárka Králíková; Miloš Buděšínský; Ivana Tomečková; Ivan Rosenberg

Publisher

Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0040-4020)

Published

2006

Language

EN

Field

Chemistry (Physical Sciences)