{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,24]],"date-time":"2025-10-24T13:14:53Z","timestamp":1761311693639,"version":"3.41.2"},"reference-count":19,"publisher":"Wiley","issue":"1","license":[{"start":{"date-parts":[[2020,5,8]],"date-time":"2020-05-08T00:00:00Z","timestamp":1588896000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100000038","name":"Natural Sciences and Engineering Research Council of Canada","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100000038","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["currentprotocols.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["CP Nucleic Acid Chemistry"],"published-print":{"date-parts":[[2020,6]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>This article contains the detailed synthesis and characterization protocols of azobenzene containing siRNAs, which have photoswitchable properties effectively controlled with light. First, the azobenzene scaffolds are synthesized via reduction of nitrophenyl alcohols in the presence of zinc. Next, the hydroxyl group of azobenzene derivatives are protected with a dimethoxytrityl (DMT) group, followed by phosphitylation with 2\u2010cyanoethyl\u2010<jats:italic>N,N<\/jats:italic>\u2010diisopropylchlorophosphoramidite. These phosphoramidite monomers are compatible with automated solid\u2010phase oligonucleotide synthesis to generate azobenzene\u2010containing oligonucleotides. \u00a9 2020 by John Wiley &amp; Sons, Inc.<\/jats:p><jats:p><jats:bold>Basic Protocol 1<\/jats:bold>: Synthesis of 4,4\u2032\u2010bis(hydroxymethyl)\u2010azobenzene phosphoramidite<\/jats:p><jats:p><jats:bold>Basic Protocol 2<\/jats:bold>: Synthesis of 4,4\u2032\u2010bis(hydroxyethyl)\u2010azobenzene phosphoramidite<\/jats:p><jats:p><jats:bold>Basic Protocol 3<\/jats:bold>: Synthesis, purification and characterization of oligonucleotides containing azobenzene derivatives<\/jats:p>","DOI":"10.1002\/cpnc.107","type":"journal-article","created":{"date-parts":[[2020,5,8]],"date-time":"2020-05-08T13:58:41Z","timestamp":1588946321000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":4,"title":["Synthesis of Azobenzene Derivative Phosphoramidites for Incorporation into Oligonucleotides"],"prefix":"10.1002","volume":"81","author":[{"given":"Matthew L.","family":"Hammill","sequence":"first","affiliation":[{"name":"Faculty of Science University of Ontario Institute of Technology  Oshawa Ontario Canada"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Jean\u2010Paul","family":"Desaulniers","sequence":"additional","affiliation":[{"name":"Faculty of Science University of Ontario Institute of Technology  Oshawa Ontario Canada"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2020,5,8]]},"reference":[{"key":"e_1_2_7_2_1","doi-asserted-by":"publisher","DOI":"10.1039\/c1cs15023e"},{"key":"e_1_2_7_3_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201202134"},{"key":"e_1_2_7_4_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.3863253"},{"issue":"1","key":"e_1_2_7_5_1","first-page":"A.3C.1\u2212A.3C.22","article-title":"Introduction to the synthesis and purification of oligonucleotides","volume":"00","author":"Ellington A.","year":"2001","journal-title":"Current Protocol Nucleic Acid Chemistry"},{"key":"e_1_2_7_6_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201503303"},{"key":"e_1_2_7_7_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201405840"},{"key":"e_1_2_7_8_1","doi-asserted-by":"publisher","DOI":"10.1002\/slct.201702322"},{"key":"e_1_2_7_9_1","doi-asserted-by":"publisher","DOI":"10.1039\/C9OB02509J"},{"key":"e_1_2_7_10_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2018.10.044"},{"key":"e_1_2_7_11_1","doi-asserted-by":"publisher","DOI":"10.1039\/JR9380000633"},{"key":"e_1_2_7_12_1","doi-asserted-by":"publisher","DOI":"10.1039\/b806406g"},{"key":"e_1_2_7_13_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201505061"},{"key":"e_1_2_7_14_1","doi-asserted-by":"publisher","DOI":"10.1002\/asia.201402758"},{"key":"e_1_2_7_15_1","doi-asserted-by":"publisher","DOI":"10.1039\/C6CS00461J"},{"key":"e_1_2_7_16_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201405885"},{"key":"e_1_2_7_17_1","doi-asserted-by":"publisher","DOI":"10.1261\/rna.753407"},{"key":"e_1_2_7_18_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200461458"},{"key":"e_1_2_7_19_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.bioconjchem.5b00125"},{"key":"e_1_2_7_20_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja01547a010"}],"container-title":["Current Protocols in Nucleic Acid Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/cpnc.107","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/cpnc.107","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/currentprotocols.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/cpnc.107","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,9,6]],"date-time":"2023-09-06T10:17:43Z","timestamp":1693995463000},"score":1,"resource":{"primary":{"URL":"https:\/\/currentprotocols.onlinelibrary.wiley.com\/doi\/10.1002\/cpnc.107"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2020,5,8]]},"references-count":19,"journal-issue":{"issue":"1","published-print":{"date-parts":[[2020,6]]}},"alternative-id":["10.1002\/cpnc.107"],"URL":"https:\/\/doi.org\/10.1002\/cpnc.107","archive":["Portico"],"relation":{},"ISSN":["1934-9270","1934-9289"],"issn-type":[{"type":"print","value":"1934-9270"},{"type":"electronic","value":"1934-9289"}],"subject":[],"published":{"date-parts":[[2020,5,8]]},"assertion":[{"value":"2020-05-08","order":2,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e107"}}