| 词条 | Fluorenylmethyloxycarbonyl protecting group |
| 释义 |
The fluorenylmethyloxycarbonyl protecting group (Fmoc) is a base-labile protecting group used in organic synthesis. ReactionsFmoc 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] It may be cleaved by bases, typically a solution of piperidine: Fmoc protection has found significant use in solid phase peptide synthesis because its removal with piperidine solution does not disturb the acid labile linker between the peptide and the resin.[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. Common amine protection methods
Common amine deprotection methods
References1. ^{{cite journal | doi = 10.1016/j.molstruc.2007.11.059 | title = A solid-state 17O NMR, X-ray, and quantum chemical study of N-α-Fmoc-protected amino acids | year = 2008 | last1 = Yamada | first1 = Kazuhiko | last2 = Hashizume | last3 = Shimizu | last4 = Ohki | last5 = Yokoyama | journal = Journal of Molecular Structure | volume = 888 | pages = 187–196 | first2 = Daisuke | first3 = Tadashi | first4 = Shinobu | first5 = Shigeyuki}} 2. ^{{cite journal | author = Paquet, A. | title = Introduction of 9-fluorenylmethyloxycarbonyl, trichloroethoxycarbonyl, and benzyloxycarbonyl amine protecting groups into O-unprotected hydroxyamino acids using succinimidyl carbonates | url = http://article.pubs.nrc-cnrc.gc.ca/ppv/RPViewDoc?issn=1480-3291&volume=60&issue=8&startPage=976 | journal = Canadian Journal of Chemistry | volume = 60 | pages = 976–980 | year = 1982 | doi = 10.1139/v82-146 | issue = 8 | deadurl = yes | archiveurl = https://archive.is/20120726095027/http://article.pubs.nrc-cnrc.gc.ca/ppv/RPViewDoc?issn=1480-3291&volume=60&issue=8&startPage=976 | archivedate = 2012-07-26 | df = }} 3. ^J. Jones, Amino Acid and Peptide Synthesis, 2nd edn., Oxford University Press, 2002. 4. ^{{Cite journal|last=Carpino|first=Louis A.|last2=Han|first2=Grace Y.|title=9-Fluorenylmethoxycarbonyl amino-protecting group|journal=The Journal of Organic Chemistry|volume=37|issue=22|pages=3404–3409|doi=10.1021/jo00795a005|year=1972}} 5. ^Wuts, P; Green, T (2006); "Greene's Protective Groups in Organic Synthesis"; DOI: 10.1002/9780470053485. 6. ^{{Cite journal|last=Farrera-Sinfreu|first=Josep|last2=Royo|first2=Miriam|last3=Albericio|first3=Fernando|date=2002-10-21|title=Undesired removal of the Fmoc group by the free ε-amino function of a lysine residue|url=http://www.sciencedirect.com/science/article/pii/S0040403902016052|journal=Tetrahedron Letters|volume=43|issue=43|pages=7813–7815|doi=10.1016/S0040-4039(02)01605-2}} 2 : Biochemistry methods|Protecting groups |
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