Scope and Limitations of γ-Valerolactone (GVL) as a Green Solvent to be Used with Base for Fmoc Removal in Solid Phase Peptide Synthesis

GVL is a green solvent used in Fmoc-based solid-phase peptide synthesis. It is susceptible to ring opening in the presence of bases such as piperidines, which are used to remove the Fmoc protecting group. Here we studied the formation of the corresponding acyl piperidides by time-dependent monitorin...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2019-11, Vol.24 (21), p.4004
Main Authors: Kumar, Ashish, Sharma, Anamika, de la Torre, Beatriz G, Albericio, Fernando
Format: Article
Language:English
Subjects:
4-methylpiperidine
acyl piperidide
Amino acids
dft
Lactones - chemistry
Magnetic Resonance Spectroscopy - methods
nmr
Peptide synthesis
Peptides
Peptides - chemistry
Pharmaceutical industry
piperidine
Piperidines - chemistry
Ring opening
Solid phases
Solid-Phase Synthesis Techniques - methods
Solvents
Solvents - chemistry
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Summary:GVL is a green solvent used in Fmoc-based solid-phase peptide synthesis. It is susceptible to ring opening in the presence of bases such as piperidines, which are used to remove the Fmoc protecting group. Here we studied the formation of the corresponding acyl piperidides by time-dependent monitoring using NMR. The results, corroborated by theoretical calculations, indicate that a solution of piperidines in GVL should be prepared daily for a better Fmoc removal.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules24214004