Fmoc chemistry (revision 2)
Old revision·00:48, 14 Jul 2024·DisparityDagny
This is an old revision of this page, as it stood at 00:48, 14 Jul 2024, saved by DisparityDagny with the summary state that overlay gas is used and name it. It may differ substantially from the current revision, and any error it contains may since have been corrected.
| Fmoc chemistry | |
|---|---|
| Temporary group | Fluorenylmethyloxycarbonyl (Fmoc), base-labile |
| Side-chain groups | Acid-labile (tBu, Trt, Pbf) |
| Deprotection reagent | Piperidine in DMF |
| Final cleavage | Trifluoroacetic acid with scavengers |
| Analytical method infobox · conventions | |
Fmoc chemistry is the protecting-group scheme that dominates modern solid-phase peptide synthesis. The temporary N-terminal group, fluorenylmethyloxycarbonyl, is removed by base; the side-chain protecting groups are removed by acid. The two are orthogonal, so each can be removed without disturbing the other.[1]
Its predecessor, Boc chemistry, used acid for both and therefore required a much stronger acid for final cleavage — hydrogen fluoride — with the handling requirements that implies. Boc chemistry was the scheme of the original solid-phase method.[2] Orthogonality is what made peptide synthesis a routine operation.[1]
References
- ^ a b Behrendt R, White P, Offer J. "Advances in Fmoc solid-phase peptide synthesis." Journal of Peptide Science 22(1):4–27 (2016). PMID 26785684.
- ^ Merrifield RB. "Solid phase peptide synthesis. I. The synthesis of a tetrapeptide." Journal of the American Chemical Society 85(14):2149–2154 (1963). DOI:10.1021/ja00897a025.
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