[{"@context":"http:\/\/schema.org\/","@type":"BlogPosting","@id":"https:\/\/wiki.edu.vn\/en\/wiki41\/fluorenylmethyloxycarbonyl-protecting-group-wikipedia\/#BlogPosting","mainEntityOfPage":"https:\/\/wiki.edu.vn\/en\/wiki41\/fluorenylmethyloxycarbonyl-protecting-group-wikipedia\/","headline":"Fluorenylmethyloxycarbonyl protecting group – Wikipedia","name":"Fluorenylmethyloxycarbonyl protecting group – Wikipedia","description":"before-content-x4 From Wikipedia, the free encyclopedia after-content-x4 The fluorenylmethoxycarbonyl protecting group (Fmoc) is a base-labile protecting group used in organic","datePublished":"2021-05-11","dateModified":"2021-05-11","author":{"@type":"Person","@id":"https:\/\/wiki.edu.vn\/en\/wiki41\/author\/lordneo\/#Person","name":"lordneo","url":"https:\/\/wiki.edu.vn\/en\/wiki41\/author\/lordneo\/","image":{"@type":"ImageObject","@id":"https:\/\/secure.gravatar.com\/avatar\/c9645c498c9701c88b89b8537773dd7c?s=96&d=mm&r=g","url":"https:\/\/secure.gravatar.com\/avatar\/c9645c498c9701c88b89b8537773dd7c?s=96&d=mm&r=g","height":96,"width":96}},"publisher":{"@type":"Organization","name":"Enzyklop\u00e4die","logo":{"@type":"ImageObject","@id":"https:\/\/wiki.edu.vn\/wiki4\/wp-content\/uploads\/2023\/08\/download.jpg","url":"https:\/\/wiki.edu.vn\/wiki4\/wp-content\/uploads\/2023\/08\/download.jpg","width":600,"height":60}},"image":{"@type":"ImageObject","@id":"https:\/\/upload.wikimedia.org\/wikipedia\/commons\/thumb\/3\/3d\/Fmoc1.png\/220px-Fmoc1.png","url":"https:\/\/upload.wikimedia.org\/wikipedia\/commons\/thumb\/3\/3d\/Fmoc1.png\/220px-Fmoc1.png","height":"150","width":"220"},"url":"https:\/\/wiki.edu.vn\/en\/wiki41\/fluorenylmethyloxycarbonyl-protecting-group-wikipedia\/","wordCount":2276,"articleBody":"     (adsbygoogle = window.adsbygoogle || []).push({});before-content-x4From Wikipedia, the free encyclopedia         (adsbygoogle = window.adsbygoogle || []).push({});after-content-x4The fluorenylmethoxycarbonyl protecting group (Fmoc) is a base-labile protecting group used in organic synthesis.         (adsbygoogle = window.adsbygoogle || []).push({});after-content-x4Mechanism of Fmoc protection of amine groupTable of ContentsProtection & Formation[edit]Cleavage & Deprotection[edit]Roles in SPPS[edit]References[edit]External links[edit]Protection & Formation[edit]Fmoc carbamate is frequently used as a protecting group for amines, where the Fmoc group can be introduced by reacting the amine with fluorenylmethyloxycarbonyl chloride (Fmoc-Cl), e.g.:[1]The other common method for introducing the Fmoc group is through 9-fluorenylmethylsuccinimidyl carbonate (Fmoc-OSu), which may itself be obtained by the reaction of Fmoc-Cl with the dicyclohexylammonium salt of N-hydroxysuccinimide.[2]       (adsbygoogle = window.adsbygoogle || []).push({});after-content-x4Reacting with 9-fluorenylmethyloxycarbonyl azide (itself made by reacting Fmoc-Cl with sodium azide) in sodium bicarbonate and aqueous dioxane is also a method to install Fmoc group.[3]Because the fluorenyl group is highly fluorescent, certain UV-inactive compounds may be reacted to give the Fmoc derivatives, suitable for analysis by reversed phase HPLC. Analytical uses of Fmoc-Cl that do not use chromatography may be limited by the requirement that excess Fmoc-Cl be removed before an analysis of fluorescence.Cleavage & Deprotection[edit]The Fmoc group is rapidly removed by primary bases as well as some secondary bases.[4] Piperidine is usually preferred for Fmoc group removal as it forms a stable adduct with the dibenzofulvene byproduct, preventing it from reacting with the substrate.[4] Fmoc protection has found significant use in solid phase peptide synthesis (SPPS).Roles in SPPS[edit]The use of Fmoc as a temporary protecting group for amine at the N-terminus in SPPS is very widespread for Fmoc\/tBu approach, because its removal with piperidine solution does not disturb the acid-labile linker between the peptide and the resin.[5] A typical SPPS Fmoc deprotection is performed with a solution of 20% piperidine in N,N-dimethylformamide (DMF).[6]Common deprotection cocktails for Fmoc during SPPS:20% piperidine in DMF (Fmoc group has an approximate half life of 6 seconds in this solution)[6]5% piperazine, 1% DBU and 1% formic acid in DMF. This method avoids the use of strictly controlled piperidine.[7] No side product was observed for a peptide with 9 residues synthesized with this method.[8]References[edit]^ Yamada, Kazuhiko; Hashizume, Daisuke; Shimizu, Tadashi; Ohki, Shinobu; Yokoyama, Shigeyuki (2008). “A solid-state 17O NMR, X-ray, and quantum chemical study of N-\u03b1-Fmoc-protected amino acids”. Journal of Molecular Structure. 888 (1\u20133): 187\u2013196. doi:10.1016\/j.molstruc.2007.11.059.^ Paquet, A. (1982). “Introduction of 9-fluorenylmethyloxycarbonyl, trichloroethoxycarbonyl, and benzyloxycarbonyl amine protecting groups into O-unprotected hydroxyamino acids using succinimidyl carbonates”. Canadian Journal of Chemistry. 60 (8): 976\u2013980. doi:10.1139\/v82-146.^ Carpino, Louis A.; Han, Grace Y. (1972). “9-Fluorenylmethoxycarbonyl amino-protecting group”. The Journal of Organic Chemistry. 37 (22): 3404\u20133409. doi:10.1021\/jo00795a005.^ a b Fields, Gregg B. (1995),  Pennington, Michael W.; Dunn, Ben M. (eds.), “Methods for Removing the Fmoc Group”, Peptide Synthesis Protocols, Methods in Molecular Biology, Totowa, NJ: Humana Press, pp.\u00a017\u201327, doi:10.1385\/0-89603-273-6:17, ISBN\u00a0978-1-59259-522-8, retrieved 2021-10-15^ J. Jones, Amino Acid and Peptide Synthesis, 2nd edn., Oxford University Press, 2002^ a b Wuts, P; Green, T (2006); “Greene’s Protective Groups in Organic Synthesis”; DOI: 10.1002\/9780470053485.^ Ralhan, Krittika; KrishnaKumar, V. Guru; Gupta, Sharad (8 December 2015). “Piperazine and DBU: a safer alternative for rapid and efficient Fmoc deprotection in solid phase peptide synthesis”. RSC Advances. 5 (126): 104417\u2013104425. doi:10.1039\/C5RA23441G. ISSN\u00a02046-2069.^ Lam, Pak-Lun; Wu, Yue; Wong, Ka-Leung (30 March 2022). “Incorporation of Fmoc-Dab(Mtt)-OH during solid-phase peptide synthesis: a word of caution”. Organic & Biomolecular Chemistry. 20 (13): 2601\u20132604. doi:10.1039\/D2OB00070A. ISSN\u00a01477-0539.External links[edit] Media related to Fmoc at Wikimedia Commons     (adsbygoogle = window.adsbygoogle || []).push({});after-content-x4"},{"@context":"http:\/\/schema.org\/","@type":"BreadcrumbList","itemListElement":[{"@type":"ListItem","position":1,"item":{"@id":"https:\/\/wiki.edu.vn\/en\/wiki41\/#breadcrumbitem","name":"Enzyklop\u00e4die"}},{"@type":"ListItem","position":2,"item":{"@id":"https:\/\/wiki.edu.vn\/en\/wiki41\/fluorenylmethyloxycarbonyl-protecting-group-wikipedia\/#breadcrumbitem","name":"Fluorenylmethyloxycarbonyl protecting group – Wikipedia"}}]}]