Study of the Staudinger Reaction and Reveal of Key Factors Affecting the Efficacy of Automatic Synthesis of Phosphoryl Guanidinic Oligonucleotide Analogs

Bazhenov, M. A.; Shernyukov, Аndrey V.; Kupryushkin, Maxim S.; Pyshnyi, D. V.

doi:10.1134/s1068162019060074

Cited by 8 publications

(5 citation statements)

References 9 publications

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“…The reactivity was tested similarly to the method described in ref ( 33 ). In screw-tight plastic tubes, ETT (0.08 mmol) and isopropanol (abs.)…”

Section: Methodsmentioning

confidence: 99%

“…Reaction of 2-azidobenzothiazole 3 with 2-cyanoethyl- N , N , N ′, N ′-tetraisopropyl diamidophosphite was carried out in an ampoule under NMR control similar to the experiment described in ref ( 33 ). To a solution of 0.5 M ETT (4 equiv, 0.112 mmol, 240 μL) in dry acetonitrile was added isopropanol (abs.)…”

Section: Methodsmentioning

confidence: 99%

“…Phosphitetriester Thymidine. Reactions of azides 1−4 with a triester were carried out under the control of 31 P NMR as described earlier 33 (Scheme 2). Initially, 5′-O-DMT-thymidine-3′-CE phosphoramidite was converted to a phosphite triester.…”

Section: Study Of Azides' Reactivity With Trivalent Phosphorus (Staud...mentioning

confidence: 99%

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Synthesis of Oligonucleotides Carrying Inter-nucleotide N-(Benzoazole)-phosphoramide Moieties

et al. 2022

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In this work, we present new oligonucleotide derivatives containing inter-nucleotide N-benzimidazole, N-benzoxazole, N-benzothiazole, and 1,3-dimethyl-N-benzimidazole (benzoazoles) phosphoramide groups. These modifications were introduced via the Staudinger reaction with appropriate azides during standard automated solid-phase oligonucleotide synthesis. The principal structural difference between the new azido modifiers and those already known is that they are bulk heterocyclic structures, similar to purine nucleoside bases. Modified oligonucleotides with one and two modifications at different positions and multiple modified heteronucleotide sequences were obtained with high yields. The possibility of multiple modifications in the process of automatic DNA synthesis is fundamental and critical for further application of our oligonucleotide derivatives. Initial studies on the properties of new oligonucleotides were carried out. The stability of the oligodeoxyribonucleotide duplex containing phosphoramide groups of N-benzoazoles with complementary DNA or RNA is slightly lower than that of native complexes.

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“…The reactivity was tested similarly to the method described in ref ( 33 ). In screw-tight plastic tubes, ETT (0.08 mmol) and isopropanol (abs.)…”

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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Synthesis of Oligonucleotides Carrying Inter-nucleotide N-(Benzoazole)-phosphoramide Moieties

et al. 2022

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“…To further improve the activity of HTT-956, we introduced PN backbone linkages to the asymmetric wings. 51 , 52 , 53 , 54 , 55 , 56 In our prior work, we evaluated the impact of stereorandom PN, R p PN, and S p PN linkages in the wings of antisense oligonucleotides targeting Malat1 and C9orf72 transcripts and noted the following observations: (1) PN linkages do not substantially alter thermal stability; (2) they have no discernable impact on the RNase H-induced cleavage pattern; and (3) they improve in vitro silencing activity compared with oligonucleotides that lack them, and this effect is not substantially impacted by the chirality or pattern of PN linkages. 38 , 57 In mice, PN backbone modifications also improved the potency, durability, and distribution of silencing throughout the CNS.…”

Section: Resultsmentioning

confidence: 99%

Preclinical evaluation of stereopure antisense oligonucleotides for allele-selective lowering of mutant HTT

Iwamoto,

Liu,

Frank-Kamenetsky

et al. 2024

Molecular Therapy - Nucleic Acids

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“…Osipov considered the problem of automatic synthesis equipment action programs in a constantly changing environment, studied the deductive and comprehensive capabilities of automated synthesis equipment cycles and self-replicating programs and proposed a method for synthesizing such action programs under various possible conditions [8]. Bazhenov introduced a new nuanced analysis of the chemical conversion that occurs during the synthesis of guanidine phosphate oligonucleotides (PGOs) by automated synthesis equipment, which gives the automated synthesis equipment better stability under deblocking conditions [9]. Satsangi confirmed in his research that the design of the reversible system of automated equipment is very different from the traditional system, explored evolutionary algorithms, and used enhanced quantum heuristic evolutionary algorithms to synthesize digital circuits and reference circuits of various automated synthesis equipment, and evolved with other algorithms, and existing search and optimization techniques were compared for performance analysis [10].…”

Section: Introductionmentioning

confidence: 99%

Carbon Nanomaterial Manufacturing System and Automatic Synthesis Equipment and Its Control Device and Control Methods

Lou

Cai

2020

Journal of Chemistry

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In recent years, people are committed to developing new technologies and technologies for energy storage and conversion, environmental detection, high-performance sensors and energy security, and other aspects of the increasingly prominent problems in the field of environmental and biosafety. The purpose of this paper is to explore the manufacturing system and automatic synthesis equipment of carbon nanomaterials, understand the control device and control method, and analyze the structure and morphology characteristics of three kinds of carbon nanomaterials produced by carbon nanomaterial manufacturing system by X-ray diffraction and infrared spectroscopy. The results show that the carbon nanomaterial manufacturing system and automatic synthesis system in this paper solve the problems of high cost, low efficiency, and small scale of the existing carbon nanomaterials manufacturing and achieve the precision control of automatic production, so that the productivity is increased by 20%–35%, and the cost is reduced by 15%–30%. Therefore, they are widely used in the fields of science and technology, environmental protection, and intelligent manufacturing broad prospects. Carbon nanotube manufacturing equipment and automatic synthesis equipment have great production advantages, which can greatly improve the quality and efficiency of carbon nanomaterials. UPY, GO, and UGO carbon nanomaterials produced by carbon nanotube manufacturing equipment are not easy to fall off from the materials. When the wavelength is 500 nm, the absorption frequency of the three materials is the largest. With the extension of the spectral wavelength, the absorption frequency of the three materials is reduced by 52%, 33%, and 34.7%, respectively.

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Study of the Staudinger Reaction and Reveal of Key Factors Affecting the Efficacy of Automatic Synthesis of Phosphoryl Guanidinic Oligonucleotide Analogs

Cited by 8 publications

References 9 publications

Synthesis of Oligonucleotides Carrying Inter-nucleotide N-(Benzoazole)-phosphoramide Moieties

Synthesis of Oligonucleotides Carrying Inter-nucleotide N-(Benzoazole)-phosphoramide Moieties

Preclinical evaluation of stereopure antisense oligonucleotides for allele-selective lowering of mutant HTT

Carbon Nanomaterial Manufacturing System and Automatic Synthesis Equipment and Its Control Device and Control Methods

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