{"id":129,"date":"2021-08-03T14:03:55","date_gmt":"2021-08-03T06:03:55","guid":{"rendered":"http:\/\/phosphoramidite.cn\/en\/?p=129"},"modified":"2021-08-03T14:07:31","modified_gmt":"2021-08-03T06:07:31","slug":"innovative-2%e2%80%b2%e2%80%91o%e2%80%91imino-2-propanoate-protecting-group-for-effective-solid-phase-synthesis-and-2%e2%80%b2%e2%80%91o%e2%80%91deprotection-of-rna-sequences","status":"publish","type":"post","link":"https:\/\/nugene.com.cn\/en\/index.php\/innovative-2%e2%80%b2%e2%80%91o%e2%80%91imino-2-propanoate-protecting-group-for-effective-solid-phase-synthesis-and-2%e2%80%b2%e2%80%91o%e2%80%91deprotection-of-rna-sequences\/","title":{"rendered":"Innovative 2\u2032\u2011O\u2011Imino-2-propanoate-Protecting Group for Effective Solid-Phase Synthesis and 2\u2032\u2011O\u2011Deprotection of RNA Sequences"},"content":{"rendered":"\n<figure class=\"wp-block-image size-full\"><img loading=\"lazy\" decoding=\"async\" width=\"605\" height=\"212\" src=\"http:\/\/phosphoramidite.cn\/en\/wp-content\/uploads\/2021\/08\/2021-08-03-135941.png\" alt=\"\" class=\"wp-image-130\" srcset=\"https:\/\/nugene.com.cn\/en\/wp-content\/uploads\/2021\/08\/2021-08-03-135941.png 605w, https:\/\/nugene.com.cn\/en\/wp-content\/uploads\/2021\/08\/2021-08-03-135941-300x105.png 300w\" sizes=\"auto, (max-width: 605px) 100vw, 605px\" \/><figcaption>The implementation of protecting groups for the 2\u2032-hydroxyl function of ribonucleosides is still challenging, particularly when RNA sequences must be of the highest purity for therapeutic applications as nucleic acid-based drugs. A 2\u2032- hydroxyl-protecting group should optimally (i) be easy to install; (ii) allow rapid and efficient incorporation of the 2\u2032-O-protected ribonucleosides into RNA sequences to minimize, to the greatest extent possible, the formation of process-related impurities (e.g., shorter than full-length sequences) during solid-phase synthesis; and (iii) be completely cleaved from RNA sequences without the production of alkylating side products and\/or formation of mutagenic nucleobase adducts. The reaction of 2\u2032-Oaminoribonucleosides with ethyl pyruvate results in the formation of stable 2\u2032-O-imino-2-methyl propanoic acid ethyl esters and, subsequently, of the fully protected ribonucleoside phosphoramidite monomers, which are required for the solid-phase synthesis of two chimeric RNA sequences (20-mers) containing the four canonical ribonucleosides. Upon treatment of the RNA sequences with a solution of sodium hydroxide, the 2\u2032-O-imino-2-methyl propanoic acid ethyl ester-protecting groups are saponified to their sodium salts, which after ion exchange underwent quantitative intramolecular decarboxylation under neutral conditions at 65 \u00b0C to provide fully deprotected RNA sequences in marginally better yields than those obtained from commercial 2\u2032-O-tert-butyldimethylsilyl ribonucleoside phosphoramidites under highly similar conditions.<\/figcaption><\/figure>\n","protected":false},"excerpt":{"rendered":"","protected":false},"author":1,"featured_media":0,"comment_status":"closed","ping_status":"closed","sticky":false,"template":"","format":"standard","meta":{"site-sidebar-layout":"default","site-content-layout":"default","ast-main-header-display":"","ast-hfb-above-header-display":"","ast-hfb-below-header-display":"","ast-hfb-mobile-header-display":"","site-post-title":"","ast-breadcrumbs-content":"","ast-featured-img":"","footer-sml-layout":"","theme-transparent-header-meta":"default","adv-header-id-meta":"","stick-header-meta":"","header-above-stick-meta":"","header-main-stick-meta":"","header-below-stick-meta":"","footnotes":""},"categories":[6,9],"tags":[10,11],"class_list":["post-129","post","type-post","status-publish","format-standard","hentry","category-news","category-rd","tag-rna-sequences","tag-solid-phase-synthesis"],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v21.1 - 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