Solid-phase Peptide Synthesis: Fmoc

Synthetic peptides are increasingly important in biochemical, pharmacological, neurobiological, enzymological and molecular biological research. Use of Fmoc as temporary amino-protecting group allows solid-phase peptide synthesis with a milder acid cleavage process. Other advances in the ligation approach provide further potential for peptide synthesis.

Keywords: resin; loading; protecting group; cleavage; ligation; SPPS

Figure 1. The scheme of the solid-phase peptide synthesis. R: side chains; X: temporary -amino protecting group; Y: side chain protecting groups.
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 References
    book Atherton E and Sheppard RC (1989) Solid Phase Peptide Synthesis: A Practical Approach Oxford: IRL Press.
    book Barany G, Albericio F, Biancalana S et al. (1992) "Biopolymer syntheses on novel polyethylene glycol-polystyrene (PEG-PS) graft supports". In: Smith AJ and River JE (eds) Peptides: Chemistry and Biology Leiden: Escoml, pp. 603–604.
    book Bayer E and Rapp W (1986) "New polymer supports for solid–liquid-phase peptide synthesis". In: Voelter W, Bayer E, Ovchinnikov YA and Ivanov VT (eds) "Chemistry of Peptides and Proteins" vol 3, Berlin: Walter de Gruyter, pp. 3–8.
    Carpino LA and Han GY (1972) The 9-fluorenylmethoxycarbonyl amino-protecting group. Journal of Organic Chemistry 37: 3404–3409.
    Fields GB and Noble RL (1990) Solid phase peptide synthesis utilizing 9-fluorenylmethoxycarbonyl amino acids. International Journal of Peptide and Protein Research 35: 161–214.
    Kempe M and Barany G (1996) CLEAR: a novel family of highly cross-linked polymeric supports for solid-phase peptide synthesis. Journal of the American Chemical Society 118: 7083–7093.
    Meldal M (1992) A flow stable polyethylene glycol dimethyl acrylamide copolymer for solid phase synthesis. Tetrahedron Letters 33: 3077–3080.
    Merrifield RB (1963) Solid phase peptide synthesis. I. The synthesis of a tetrapeptide. Journal of the American Chemical Society 85: 2149–2153.
    Schnolzer M and Kent SBH (1992) Constructing proteins by dovetailing unprotected synthetic peptides: backbone-engineered HIV protease. Science 256: 221–225.
 Further Reading
    book Fields GB, Lauer-Fields JL, Liu RQ and Barany G (2002) "Principles and practice of solid-phase peptide synthesis". In: Grant GA (ed.) Synthetic Peptides, A User's Guide, 2nd edn, pp. 93–219. New York: Oxford University Press.
    book Grant G (2002) "Evaluation of the synthetic product". In Grant GA (ed.) Synthetic Peptides, A User's Guide, 2nd edn, pp. 220–291. New York: Oxford University Press.
    book Chan WC and White PD (2002) Fmoc Solid Phase Peptide Synthesis, A Practical Approach. New York: Oxford University Press.
    book Pennington MW and Dunn BM (1994) "Peptide synthesis protocol". Methods in Molecular Biology 35. Totowa, NJ: Humana Press.
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How to Cite close
Yang, Chi C(May 2005) Solid-phase Peptide Synthesis: Fmoc. In: eLS. John Wiley & Sons Ltd, Chichester. http://www.els.net [doi: 10.1038/npg.els.0002693]