Related Experiment Video

Updated: Jan 4, 2026

Modification and Functionalization of the Guanidine Group by Tailor-made Precursors

Modification and Functionalization of the Guanidine Group by Tailor-made Precursors

Published on: April 27, 2017

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

Ashish Kumar^1,2, Anamika Sharma^1,2, Beatriz G de la Torre²

¹Peptide Science Laboratory, School of Chemistry and Physics, University of KwaZulu-Natal, Durban 4001, South Africa.

Molecules (Basel, Switzerland)

|November 8, 2019

Abstract:

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.

Keywords:

4-methylpiperidine DFT IR NMR acyl piperidide piperidine

More Related Videos

An Inexpensive Adaptation of a Commercial Microwave Reactor for Solid Phase Peptide Synthesis

An Inexpensive Adaptation of a Commercial Microwave Reactor for Solid Phase Peptide Synthesis

Published on: November 22, 2024

Hydrolysis of a Ni-Schiff-Base Complex Using Conditions Suitable for Retention of Acid-labile Protecting Groups

Hydrolysis of a Ni-Schiff-Base Complex Using Conditions Suitable for Retention of Acid-labile Protecting Groups

Published on: April 6, 2017

Related Concept Videos

Limitations of Friedel–Crafts Reactions

Limitations of Friedel–Crafts Reactions

Several restrictions limit the use of Friedel–Crafts reactions. First, the halogen in the alkyl halide must be attached to an sp3-hybridized carbon for the Friedel–Crafts reactions to occur. Vinyl or aryl halides do not react since the carbocations formed are unstable under the reaction conditions. Second, Friedel–Crafts alkylation is susceptible to carbocation rearrangement, and the major products obtained have a rearranged carbon skeleton. In contrast, the acylium ion is...

Preparation of Carboxylic Acids: Carboxylation of Grignard Reagents

Preparation of Carboxylic Acids: Carboxylation of Grignard Reagents

Carboxylic acids can be prepared by the carboxylation of Grignard reagents (RMgX). This method is convenient for converting alkyl (primary, secondary or tertiary), vinyl, benzyl, and aryl halides to carboxylic acids with one additional carbon than the starting RMgX.

Articles linked to this work by shared authors, journal, and citation graph.

Head-to-Tail Cyclization and D-Amino Acid Substitution Redesign the Biological Activities of a Naturally Occurring Amphibian Peptide.

Molecules (Basel, Switzerland)·2026

Targeting PIKfyve: Chemical Biology and Drug Discovery Insights.

Chemical biology & drug design·2026

Symmetrical Branching Unit Alternative to Lysine-Core-Based Multiple Antigenic Peptides to Eradicate Isomeric Impurities.

Organic letters·2026

Antibiotic Resistance: From the Bench to Patients, 2.0.

Antibiotics (Basel, Switzerland)·2026

Native MS and ligand observed NMR uncovers subtle SLiM binding variations that mediate HSP90-Hop PPI modulation.

RSC chemical biology·2026

Multifactorial Perspective for Greening Solid-Phase Peptide Synthesis: Rigid Polyacrylate Macroporous Resin in Combination with Green Solvents.

ChemSusChem·2026

See all related articles