Addressing regio- And stereo-specificity challenges in the synthesis of nucleoside 2′,3′-cyclic monophosphate analogs-a rapid and facile synthesis of nucleoside-2′,3′-: O, O -phosphoro-thioate or -selenoate, and elucidation of the origin of the rare specificity

Molhm Nassir; Lara Balaom; Bilha Fischer

doi:10.1039/d0cc02886j

Addressing regio- And stereo-specificity challenges in the synthesis of nucleoside 2′,3′-cyclic monophosphate analogs-a rapid and facile synthesis of nucleoside-2′,3′-: O, O -phosphoro-thioate or -selenoate, and elucidation of the origin of the rare specificity

Molhm Nassir, Lara Balaom, Bilha Fischer

Department of Chemistry

University of Bonn

Research output: Contribution to journal › Article › peer-review

2 Scopus citations

Abstract

A new facile, rapid, stereo- and regio-selective one-pot synthesis of nucleoside-2′,3′-O,O-phosphorothioate and selenoate analogs has been developed. This method avoids the need for protection strategies and chiral reagents, chiral metal catalysts, or chiral separations. This synthetic method has been applied to all natural nucleosides (U/A/G/C/T). Furthermore, we have deciphered the origin of the stereo- and regio-selectivity of the reaction.

Original language	English
Pages (from-to)	11633-11636
Number of pages	4
Journal	Chemical Communications
Volume	56
Issue number	78
DOIs	https://doi.org/10.1039/d0cc02886j
State	Published - 1 Oct 2020

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© 2020 The Royal Society of Chemistry.

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Nassir, M., Balaom, L., & Fischer, B. (2020). Addressing regio- And stereo-specificity challenges in the synthesis of nucleoside 2′,3′-cyclic monophosphate analogs-a rapid and facile synthesis of nucleoside-2′,3′-: O, O -phosphoro-thioate or -selenoate, and elucidation of the origin of the rare specificity. Chemical Communications, 56(78), 11633-11636. https://doi.org/10.1039/d0cc02886j

Nassir, Molhm ; Balaom, Lara ; Fischer, Bilha. / Addressing regio- And stereo-specificity challenges in the synthesis of nucleoside 2′,3′-cyclic monophosphate analogs-a rapid and facile synthesis of nucleoside-2′,3′- : O, O -phosphoro-thioate or -selenoate, and elucidation of the origin of the rare specificity. In: Chemical Communications. 2020 ; Vol. 56, No. 78. pp. 11633-11636.

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abstract = "A new facile, rapid, stereo- and regio-selective one-pot synthesis of nucleoside-2′,3′-O,O-phosphorothioate and selenoate analogs has been developed. This method avoids the need for protection strategies and chiral reagents, chiral metal catalysts, or chiral separations. This synthetic method has been applied to all natural nucleosides (U/A/G/C/T). Furthermore, we have deciphered the origin of the stereo- and regio-selectivity of the reaction.",

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Nassir, M, Balaom, L & Fischer, B 2020, 'Addressing regio- And stereo-specificity challenges in the synthesis of nucleoside 2′,3′-cyclic monophosphate analogs-a rapid and facile synthesis of nucleoside-2′,3′-: O, O -phosphoro-thioate or -selenoate, and elucidation of the origin of the rare specificity', Chemical Communications, vol. 56, no. 78, pp. 11633-11636. https://doi.org/10.1039/d0cc02886j

Addressing regio- And stereo-specificity challenges in the synthesis of nucleoside 2′,3′-cyclic monophosphate analogs-a rapid and facile synthesis of nucleoside-2′,3′-: O, O -phosphoro-thioate or -selenoate, and elucidation of the origin of the rare specificity. / Nassir, Molhm; Balaom, Lara; Fischer, Bilha.
In: Chemical Communications, Vol. 56, No. 78, 01.10.2020, p. 11633-11636.

Research output: Contribution to journal › Article › peer-review

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Nassir M, Balaom L, Fischer B. Addressing regio- And stereo-specificity challenges in the synthesis of nucleoside 2′,3′-cyclic monophosphate analogs-a rapid and facile synthesis of nucleoside-2′,3′-: O, O -phosphoro-thioate or -selenoate, and elucidation of the origin of the rare specificity. Chemical Communications. 2020 Oct 1;56(78):11633-11636. doi: 10.1039/d0cc02886j

Addressing regio- And stereo-specificity challenges in the synthesis of nucleoside 2′,3′-cyclic monophosphate analogs-a rapid and facile synthesis of nucleoside-2′,3′-: O, O -phosphoro-thioate or -selenoate, and elucidation of the origin of the rare specificity

Abstract

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