TY - JOUR

T1 - Synthesis of Novel Representatives of Phosphoryl Guanidine Oligonucleotides

AU - Zhukov, S. A.

AU - Pyshnyi, D. V.

AU - Kupryushkin, M. S.

N1 - Funding Information: This study was supported by the base budgetary financing of the Program of the Basic Scientific Research of the State Scientific Academies in 2013–2020, projects nos. АААА-А17-117020210024-8. M.S. Kupryushkin thanks the Russian Scientific Foundation (project no. 19-14-00204) for the support of the synthesis and characterization of the native and modified oligonucleotides. Publisher Copyright: © 2021, Pleiades Publishing, Ltd. Copyright: Copyright 2021 Elsevier B.V., All rights reserved.

PY - 2021/3

Y1 - 2021/3

N2 - Novel representatives of phosphoryl guanidine oligonucleotide derivatives were prepared in this study. A synthetic scheme has been proposed and implemented suitable for the preparation of a wide range of diaminocarbenium azides starting from various secondary amines for subsequent incorporation of tetrasubstituted guanidine residues into the oligonucleotides by the Staudinger reaction. A number of factors which affected the yield of the phosphoryl guanidine derivative were identified, in particular, the size of the alkyl substituents in the azide used, the purity of the azide, and the conditions for elimination of the protecting cyanoethyl group before the final deprotection of the oligonucleotide.

AB - Novel representatives of phosphoryl guanidine oligonucleotide derivatives were prepared in this study. A synthetic scheme has been proposed and implemented suitable for the preparation of a wide range of diaminocarbenium azides starting from various secondary amines for subsequent incorporation of tetrasubstituted guanidine residues into the oligonucleotides by the Staudinger reaction. A number of factors which affected the yield of the phosphoryl guanidine derivative were identified, in particular, the size of the alkyl substituents in the azide used, the purity of the azide, and the conditions for elimination of the protecting cyanoethyl group before the final deprotection of the oligonucleotide.

KW - automatic oligonucleotide synthesis

KW - modified oligonucleotides

KW - organic azides

KW - phosphoryl guanidine oligonucleotides (PGOs)

KW - phosphoryl guanidines

KW - the Staudinger reaction

UR - http://www.scopus.com/inward/record.url?scp=85104823487&partnerID=8YFLogxK

U2 - 10.1134/S1068162021020291

DO - 10.1134/S1068162021020291

M3 - Article

AN - SCOPUS:85104823487

VL - 47

SP - 380

EP - 389

JO - Russian Journal of Bioorganic Chemistry

JF - Russian Journal of Bioorganic Chemistry

SN - 1068-1620

IS - 2

ER -