alkyne protecting group

However, the use of expensive silicon protected acetylene reagents and/or stoichio-metric AgF restricts these method to … 2018;66(2):147-154. doi: 10.1248/cpb.c17-00696. 2013;32(6):306-19. doi: 10.1080/15257770.2013.787147. This site needs JavaScript to work properly. The functionalized protecting groups were deprotected by a nitroreductase/NADH reduction system to give "naked" oligonucleotides. Synthesis and Characterization of Cell-Permeable Oligonucleotides Bearing Reduction-Activated Protecting Groups on the Internucleotide Linkages. TMS as an alkyne protecting group is not satisfactory, the TIPS group is a valid alternative and its removal can be efficiently accomplished with stoichiometric AgF. Copyright © 2017 Elsevier Ltd. All rights reserved. This method allowed the synthesis of oligonucleotide prodrugs bearing the functionalized protecting group at the desired sites and desired residues on oligodeoxyribonucleotide (ODN) backbones. The azide can be used for a “click” reaction and the TIPS group can be removed following polymerization, allowing the alkyne … The bulk of a silane can protect an acetylene against catalytic hydrogenation because of rate differences between an olefin (primary or secondary) vs. the more hindered protected alkyne. A versatile conjugatable/bioreduction-responsive protecting group for phosphodiester moieties was designed, synthesized and incorporated into oligonucleotide strands. Following early reports on PPGs for use in organic … Please check your email for instructions on resetting your password. Published by Elsevier Ltd. Saneyoshi H, Yamamoto Y, Kondo K, Hiyoshi Y, Ono A. J Org Chem. Use the link below to share a full-text version of this article with your friends and colleagues. We compare the new photolabile protecting group with the commonly used alkyne protecting group, 2-methyl-3-butyn-2-ol and the results show that NB ethers are stable under the cleaving conditions for the cleavage of methylbutynol protected alkynes. Please enable it to take advantage of the complete set of features! Find NCBI SARS-CoV-2 literature, sequence, and clinical content: Epub 2017 Jan 23. ScienceDirect ® is a registered trademark of Elsevier B.V. ScienceDirect ® is a registered trademark of Elsevier B.V. A photolabile protection strategy for terminal alkynes. Several photo-caged alcohols were synthesized via mild copper(II)-catalyzed substitution between tertiary propargylic alcohols and 2-nitrobenzyl alcohol to build up robust, base stable o-nitrobenzyl (NB) photo-cleavable compounds. We present a strategy for photolabile protection of terminal alkynes. 2016 Sep 21;27(9):2149-56. doi: 10.1021/acs.bioconjchem.6b00368. Nucleosides Nucleotides Nucleic Acids. If you do not receive an email within 10 minutes, your email address may not be registered, Trialkylsilylacetylenes are often used as a convenient method for introducing an acetylenic unit because they tend to be easily handled liquids or solids, as opposed to gaseous acetylene. Conjugation; Drug delivery; Oligonucleotide therapeutics; Protecting group. We use cookies to help provide and enhance our service and tailor content and ads. Subsequently, controlled pore glass-supported oligonucleotides were conjugated to a variety of functional molecules using a copper-catalyzed azide-alkyne cycloaddition reaction. 1: eg. Copyright © 2020 Elsevier B.V. or its licensors or contributors. Nucleosides Nucleotides Nucleic Acids. NLM A protecting group (PG) is a molecular framework that is introduced onto a specific functional group (FG) in a poly-functional molecule to block its reactivity under reaction conditions needed to make modifications elsewhere in the molecule.

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