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

Bar-Ilan University

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

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 GB
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

ASJC Scopus subject areas

Electronic, Optical and Magnetic Materials
General Chemistry
Ceramics and Composites
Metals and Alloys
Materials Chemistry
Surfaces, Coatings and Films
Catalysis

Access to Document

10.1039/d0cc02886j

Fingerprint

Dive into the research topics of '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'. Together they form a unique fingerprint.

Cite this

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.

@article{30922a4f31c648e391585a638c0e1a00,

title = "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 = "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.",

author = "Molhm Nassir and Lara Balaom and Bilha Fischer",

note = "Publisher Copyright: {\textcopyright} 2020 The Royal Society of Chemistry.",

year = "2020",

month = oct,

day = "1",

doi = "10.1039/d0cc02886j",

language = "الإنجليزيّة",

volume = "56",

pages = "11633--11636",

number = "78",

}

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

TY - JOUR

T1 - 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′-

T2 - O, O -phosphoro-thioate or -selenoate, and elucidation of the origin of the rare specificity

AU - Nassir, Molhm

AU - Balaom, Lara

AU - Fischer, Bilha

PY - 2020/10/1

Y1 - 2020/10/1

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/85092600600

U2 - 10.1039/d0cc02886j

DO - 10.1039/d0cc02886j

M3 - مقالة

C2 - 32870217

SN - 1359-7345

VL - 56

SP - 11633

EP - 11636

JO - Chemical Communications

JF - Chemical Communications

IS - 78

ER -

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

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this