Fluorenylmethyloxycarbonyl chloride

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Fluorenylmethyloxycarbonyl chloride[1]
Fmoc-2D-skeletal.png
Identifiers
CAS number 28920-43-6 YesY
PubChem 34367
ChemSpider 31647 YesY
Jmol-3D images Image 1
Properties
Molecular formula C15H11ClO2
Molar mass 258.70 g mol−1
Melting point 62-64 °C
Hazards
EU classification Corrosive (C)
R-phrases R34
S-phrases S26 S36/37/39 S45
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY (verify) (what is: YesY/N?)
Infobox references

Fluorenylmethyloxycarbonyl chloride (FMOC-Cl) is a chloroformate ester. It is used to introduce FMOC group as the FMOC carbamate.

Preparation[edit]

This compound may be prepared by reacting 9-fluorenylmethanol with phosgene:[2]

Preparation of Fmoc-Cl.png

Reactions[edit]

The FMOC carbamate is often used as a protecting group for amines. The FMOC group can be introduced by reacting the amine with FMOC-Cl, e.g.:[3]

Scheme showing addition of an Fmoc group to an amino acid

The other common method for introducing the FMOC group is through 9-fluorenylmethyl succinimidyl carbonate (FMOC-OSu), which may itself be obtained by the reaction of FMOC-Cl with the dicyclohexylammonium salt of N-hydroxysuccinimide.[4]

It may be cleaved by bases, typically a solution of piperidine:

Mechanism of the deprotection of the Fmoc group with 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.[5]

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.

References[edit]

  1. ^ Fmoc chloride at Sigma-Aldrich
  2. ^ Carpino, Louis A.; Han, Grace Y. (1972). "9-Fluorenylmethoxycarbonyl amino-protecting group". The Journal of Organic Chemistry 37 (22): 3404. doi:10.1021/jo00795a005. 
  3. ^ Yamada, Kazuhiko; Hashizume, Daisuke; Shimizu, Tadashi; Ohki, Shinobu; Yokoyama, Shigeyuki (2008). "A solid-state 17O NMR, X-ray, and quantum chemical study of N-α-Fmoc-protected amino acids". Journal of Molecular Structure 888: 187. doi:10.1016/j.molstruc.2007.11.059. 
  4. ^ 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. doi:10.1139/v82-146. 
  5. ^ J. Jones, Amino Acid and Peptide Synthesis, 2nd edn., Oxford University Press, 2002.