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Issue 4, 2019
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Environmentally friendly SPPS I. Application of NaOH in 2-MeTHF/methanol for Fmoc removal

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Abstract

Focusing on the step-by-step transformation of the traditional solid-phase peptide synthesis (SPPS) into an environmentally friendly process, we herein report the elimination of environmentally hazardous components (piperidine, DMF and DCM) from this technique. We developed a synthetic protocol that employs sodium hydroxide in a 2-MeTHF/MeOH mixture for Fmoc group cleavage and uses 2-MeTHF alone as the coupling solvent. The protocol was developed with the most frequently used PS/DVB-based resin. This synthetic strategy was used to prepare Leu-enkephalin amide, and the results (crude purity 99%, yield 62%) were fully comparable to those achieved with the traditional protocol using piperidine, DMF and DCM.

Graphical abstract: Environmentally friendly SPPS I. Application of NaOH in 2-MeTHF/methanol for Fmoc removal

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Publication details

The article was received on 03 Dec 2018, accepted on 18 Jan 2019 and first published on 18 Jan 2019


Article type: Communication
DOI: 10.1039/C8GC03778G
Citation: Green Chem., 2019,21, 775-779

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    Environmentally friendly SPPS I. Application of NaOH in 2-MeTHF/methanol for Fmoc removal

    A. Přibylka, V. Krchňák and E. Schütznerová, Green Chem., 2019, 21, 775
    DOI: 10.1039/C8GC03778G

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