Synthesis of the new nucleoside 5′-alpha-iminophosphates using Staudinger reaction

Synthesis of the new nucleoside 5′-alpha-iminophosphates using Staudinger reaction Full article

Journal

Bioorganic Chemistry
ISSN: 0045-2068

Output data

Year: 2022, Volume: 127, Article number : 105987, Pages count : DOI: 10.1016/j.bioorg.2022.105987

Tags

Alpha-phosphate mimetic nucleotides; Nucleoside 5′-α-iminophosphates; Staudinger reaction; Terminal deoxynucleotidyl transferase substrate

Authors

Vasilyeva S.V. ¹ , Kuznetsova A.A. ¹ , Baranovskaya E.E. ¹ , Kuznetsov N.A. ¹ , Lomzov A.A. ¹ , Pyshnyi D.V. ¹

Affiliations

1	Institute of Chemical Biology & Fundamental Medicine, SB of RAS, pr. Lavrent’eva 8, 630090 Novosibirsk, Russia

Efficient protocols were developed for the synthesis of a new compounds - nucleoside 5′-α-iminophosphates using the Staudinger reaction. These substances are alpha-phosphate mimetic nucleotide in which an oxygen atom is replaced by a corresponding imino (=N-R)-group. Various 5′-iminomonophosphates of nucleosides were obtained. A chemical method for the synthesis of triphosphate derivatives based on the iminomonophosphates has been designed. Thymidine 5′-(1,3-dimethylimidazolidin-2-ylidene)-triphosphate (ppp(DMI)T) was synthesized, its hydrolytic stability and substrate properties in relation to some DNA polymerases was firstly studied. It was shown that ppp(DMI)T can serve as substrate for enzyme catalyzed template-independent DNA synthesis by human terminal deoxynucleotidyltransferase TdT.

Vasilyeva S.V. , Kuznetsova A.A. , Baranovskaya E.E. , Kuznetsov N.A. , Lomzov A.A. , Pyshnyi D.V.
Synthesis of the new nucleoside 5′-alpha-iminophosphates using Staudinger reaction
Bioorganic Chemistry. 2022. V.127. 105987 . DOI: 10.1016/j.bioorg.2022.105987 WOS Scopus OpenAlex

Web of science:	WOS:000826700300004
Scopus:	2-s2.0-85132892630
OpenAlex:	W4283576186

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