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Title: Deprotection reagents in Fmoc solid phase peptide synthesis: Moving away from piperidine?
Author: Luna, Omar F.
Gomez, Johana
Cardenas, Constanza
Albericio Palomera, Fernando
Marshall, Sergio H.
Guzman, Fanny
Keywords: Síntesi de pèptids
Peptide synthesis
Issue Date: 15-Nov-2016
Publisher: MDPI
Abstract: The deprotection step is crucial in order to secure a good quality product in Fmoc solid phase peptide synthesis. 9-Fluorenylmethoxycarbonyl (Fmoc) removal is achieved by a two-step mechanism reaction favored by the use of cyclic secondary amines; however, the efficiency of the reaction could be affected by side reactions and by-product formation. Several aspects have to be taken into consideration when selecting a deprotection reagent: its physicochemical behavior, basicity (pKa) and polarity, concentration, and time of reaction, toxicity and disposability of residues and, finally, availability of reagents. This report presents a comparison of the performance of three strategies for deprotection using microwave-assisted Fmoc peptide synthesis. Four peptide sequences were synthesized using Rink amide resin with a Liberty Blue automated synthesizer and 4-methylpiperidine (4MP), piperidine (PP), and piperazine (PZ) as Fmoc removal reagents. In the first instance all three reagents behaved similarly. A detailed analysis showed a correlation between the hydrophobicity and size of the peptide with the yield and purity of the obtained product. The three reagents are interchangeable, and replacement of piperidine could be advantageous regarding toxicity and reagent handling.
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It is part of: Molecules, 2016, vol. 21, num. 11, p. 1542
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ISSN: 1420-3049
Appears in Collections:Articles publicats en revistes (Química Inorgànica i Orgànica)

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