Azide Phosphoramidite in Direct Synthesis of Azide-Modified Oligonucleotides

Fomich, Maksim A.; Kvach, Maksim V.; Navakouski, Maksim; Weise, Christoph; Baranovsky, A. V.; Korshun, Vladimir A.; Shmanai, Vadim V.

doi:10.1021/ol502155g

Cited by 27 publications

(29 citation statements)

References 65 publications

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“…Although DMAP is more available than silver salts, longer reaction time and higher temperature were mostly used for secondary alcohols. 3a,4 Other strategies to facilitate tritylation of secondary alcohols include using a stronger base such as DBU and NaH to deprotonated the alcohol. 5 However, NaH may have substrate compatibility issues, and when DBU was used, long reaction time was required.…”

Section: Introductionmentioning

confidence: 99%

Tritylation of alcohols under mild conditions without using silver salts

Shahsavari

Chen

Wigstrom

et al. 2016

Tetrahedron Letters

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Secondary alcohols were conveniently tritylated under mild conditions within a short running time with tritylium trifluoroacetate generated in situ from trityl alcohols and trifluoroacetic anhydride. No expensive silver salts were needed for the reactions. Four secondary alcohols were tritylated with both mono- and dimethoxy trityl alcohols giving good to excellent isolated yields. The reaction was also tested on four nucleoside derivatives that have primary alcohols. Satisfactory results were also obtained.

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Section: Introductionmentioning

confidence: 99%

Tritylation of alcohols under mild conditions without using silver salts

Shahsavari

Chen

Wigstrom

et al. 2016

Tetrahedron Letters

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“…Выход 140 мг (84 % от теор.). 70,130,38,130,19,128,09,127,93,80,25,69,94,62,04,34,32,31,67,29,75,29,50,29,30,29,25,29,22,27,35,25,06,22,72,14,22. ТСХ: R f 0,50 (10 % EtOAc/ПЭ).…”

Section: экспериментальная частьunclassified

“…В данной работе мы предлагаем улучшенный подход, основанный на реакции CuAAC. Он отличается тем, что вначале при помощи ранее разработанных реагентов [29] мы вводим азидную группу в 3′-или 5′-положение олигонуклеотида, а лишь затем полученный олигонуклеотид с азидной группой конъюгируем с алкин-содержащим липидом. Преимущества этого подхода состоят в большей универсальности.…”

unclassified

Synthesis of Conjugates of Oligonucleotides and 11,11-D2-Linoleic Acid Derivatives via Azide-Alkyne Cycloaddition

Fomich¹,

Bekish²,

Шарко³

et al. 2018

Vescì Akademìì navuk Belarusì. Seryâ himičnyh navuk

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СИНТЕЗ КОНъЮГАТОВ ОЛИГОНУКЛЕОТИДОВ С ПРОИЗВОДНЫмИ 11,11-D 2-ЛИНОЛЕВОЙ КИСЛОТЫ ПО РЕАКцИИ АЗИД-АЛКИНОВОГО цИКЛОПРИСОЕДИНЕНИЯ Аннотация. Предложен новый подход к синтезу конъюгатов олигонуклеотидов и жирных кислот, основанный на медь-катализируемой реакции циклоприсоединения азидсодержащих олигонуклеотидов к производным жирных кислот с терминальной тройной связью (CuAAC). Для демонстрации этого подхода осуществлен синтез пяти производных 11,11-D 2-линолевой кислоты, содержащих концевую тройную связь в различных частях молекулы. Разработана методика их конъюгации с азидсодержащим модельным олигонуклеотидом Т 20 , проверено влияние различных условий (времени, концентрации катализатора, избытка алкинсодержащего реагента, состава растворителя и др.) на выход продукта. Такие конъюгаты устойчивы в биологических средах, обладают повышенной способностью проникать в клетки и могут найти применение в качестве средств генной терапии. Ключевые слова: полиненасыщенные жирные кислоты, олигонуклеотиды, биоконъюгаты, клик-химия Для цитирования. Синтез конъюгатов олигонуклеотидов с производными 11,11-D 2-линолевой кислоты по реакции азид-алкинового циклоприсоединения / М. А. Фомич [и др.] // Вес. Нац. акад. навук Беларусі. Сер. хім.

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“…Most recently, it was found that azide and phosphoramidite functions are compatible with each other in artificial building block 9 . Accordingly, azide‐bearing oligonucleotides were prepared and provided full postsynthetic click functionality 26 …”

Section: Copper‐catalyzed Azide–alkyne Cycloaddition (Cuaac) and Tmentioning

confidence: 99%

Copper‐Free Postsynthetic Labeling of Nucleic Acids by Means of Bioorthogonal Reactions

et al. 2015

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Postsynthetic modification of nucleic acids has the advantage that the chemical development of only a few building blocks is necessary, each bearing a chosen reactive functional group that is applicable to its reactive counterpart for a variety of different labeling types. The reactive group is either linked to phosphoramidites for chemical synthesis on solid phase or attached to nucleoside triphosphates for application in primer extension experiments and PCR. Chemoselectivity is required for this strategy, together with bioorthogonality to perform these labelings in living cells or even organisms. Currently, the copper-free reactions include strain-promoted 1,3-dipolar cycloadditions, "photoclick" reactions, Diels-Alder reactions with inverse electron demand, and nucleophilic additions. The majority of these modification strategies show good to excellent reaction kinetics, an important prerequisite for labeling inside cells and in vivo in order to keep the concentrations of the reacting partners as low as possible.

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Azide Phosphoramidite in Direct Synthesis of Azide-Modified Oligonucleotides

Cited by 27 publications

References 65 publications

Tritylation of alcohols under mild conditions without using silver salts

Tritylation of alcohols under mild conditions without using silver salts

Synthesis of Conjugates of Oligonucleotides and 11,11-D2-Linoleic Acid Derivatives via Azide-Alkyne Cycloaddition

Copper‐Free Postsynthetic Labeling of Nucleic Acids by Means of Bioorthogonal Reactions

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