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Base sensitive amino protecting group for solid-phase peptide synthesis9-Fluorenylmethyl chloroformate is used in capillary electrophoresis. It acts as a reagent in the precolumn derivatization of amines for HPLC and fluorescent detection. Further, it is used for derivatizing amino acids for HPLC analysis. In addition to this, it is used to prepare N-Fmoc amino acids for solid-phase peptide synthesis and oligonucleotide synthesis.
Reagent for the protection of amino groups in peptide synthesis (see Appendix 6) as their 9-fluorenylmethoxycarbonyl (Fmoc) derivatives: J. Org. Chem., 37, 3404 (1972); J. Am. Chem. Soc., 96, 4987 (1974); 99, 7363 (1977). Review: Acc. Chem. Res., 20, 401 (1987). They are particularly applicable in solid-phase peptide synthesis. The stability of Fmoc-protected amino acids to acidic conditions permits their conversion in many cases to the acid chlorides as active intermediates for peptide coupling, resistant to racemization, in contrast to other protected amino acid chlorides. For a review of peptide synthesis via amino acid halides, see: Acc. Chem. Res., 29, 268 (1996).
In the presence of triethylamine, reacts with Pentafluorophenol, A15574 , to give the PFP carbonate, a useful active ester for the preparation of Fmoc-amino acids. Moreover, the active PFP ester of the protected amino acid can be obtained by in situ DCC coupling with the liberated PFP: Synthesis, 303 (1986).
Cleavage of the Fmoc group occurs under mildly basic conditions:
Ethanolamine: J. Am. Chem. Soc., 92, 5748 (1970); J. Org. Chem., 37, 3404 (1972). Piperidine: J. Org. Chem., 52, 1197 (1987); applicable to solid-phase peptide synthesis.
TBAF in DMF; rapid reaction at room temperature: Tetrahedron Lett., 28, 6617 (1987). For both the deblocking of Fmoc-protected amino acids and for the removal of excess reagent during the protection step, 4-(Aminomethyl)piperidine, L11577 , has been recommended: J. Org. Chem., 51, 3732 (1986); 55, 721 (1990), particularly in conjunction with Fmoc-protected acid chlorides as the active species. Even better results have been obtained with Tris(2-aminoethyl)amine, B21789 , in this type of chemistry: J. Org. Chem., 55, 1673 (1990).
Limited use has also been made in the protection of alcohols as 9-fluorenylmethyl carbonates, rapidly cleaved by triethylamine: J. Chem. Soc., Chem. Commun., 672 (1982).
Zhou, Y.; Lin, Q.; Jin, C.; Cheng, L.; Zheng, X.; Dai, M.; Zhang, Y. Simultaneous Analysis of N-epsilon-(Carboxymethyl) Lysine and N-epsilon-(Carboxyethyl) Lysine in Foods by Ultra-Performance Liquid Chromatography-Mass Spectrometry with Derivatization by 9-Fluorenylmethyl Chloroformate. J. Food Sci. 2015, 80 (2), C207-C217.
Boonchiangma, S.; Ratchakrut, P.; Chanthai, S.; Srijaranai, S. Reversed Phase Chromatographic Analysis of 13 Amino Acids in Honey Samples. Chromatographia 2015, 78 (13), 923-927.
Hazard Statements: H302-H312-H314-H332-H335
Harmful if swallowed. Harmful in contact with skin. Causes severe skin burns and eye damage. Harmful if inhaled. May cause respiratory irritation.
Precautionary Statements: P260-P264b-P270-P271-P280-P303+P361+P353-P304+P340-P305+P351+P338-P310-P330-P331-P363-P501c
Do not breathe dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER or doctor/physician. Rinse mouth. Do NOT induce vomiting. Wash contaminated clothing before reuse. Dispose of contents/ container to an approved waste disposal plant