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Molecules 2016, 21(11), 1542; doi:10.3390/molecules21111542

Deprotection Reagents in Fmoc Solid Phase Peptide Synthesis: Moving Away from Piperidine?

1
Fraunhofer Chile Research, Santiago 7550296, Chile
2
Núcleo Biotecnología Curauma, Pontificia Universidad Católica de Valparaíso, Valparaíso 2373223, Chile
3
CIBER-BBN, Networking Centre on Bioengineering, Biomaterials and Nanomedicine, University of Barcelona, Barcelona 08028, Spain
4
Department of Organic Chemistry, University of Barcelona, Barcelona 08028, Spain
5
School of Chemistry, University of KwaZulu-Natal, Durban 4001, South Africa
6
Instituto de Biología, Pontificia Universidad Católica de Valparaíso, Valparaíso 2373223, Chile
*
Author to whom correspondence should be addressed.
Academic Editor: Roman Dembinski
Received: 17 October 2016 / Revised: 8 November 2016 / Accepted: 12 November 2016 / Published: 15 November 2016
(This article belongs to the Section Organic Synthesis)
View Full-Text   |   Download PDF [2567 KB, uploaded 18 November 2016]   |  

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. View Full-Text
Keywords: N-α-deprotection reagent; piperazine; piperidine; 4-methylpiperidine; solid-phase peptide synthesis N-α-deprotection reagent; piperazine; piperidine; 4-methylpiperidine; solid-phase peptide synthesis
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Luna, O.F.; Gomez, J.; Cárdenas, C.; Albericio, F.; Marshall, S.H.; Guzmán, F. Deprotection Reagents in Fmoc Solid Phase Peptide Synthesis: Moving Away from Piperidine? Molecules 2016, 21, 1542.

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