4-Methylpiperidine The highly efficient reagent for removal of 9-Fluorenylmethoxycarbonyl (Fmoc) protection group. Compatible with solid-phase synthesis.
CAS: 626-58-4
Synonym: γ-Pipecoline, 4-Pipecoline, 4-MP
Properties
Purity
≥98.0%
Molecular Formula
C6H13N
Molecular Weight
99.17 [gr/mol]
Appearance
Colorless to light-colored liquid
Storage Conditions
Store refrigirated (2-8oC)
Applications
- Fmoc deprotection reagent.
- Compatible with SPPS and microwave-assisted SPPS.
- Interchangeable with Piperidine deprotection agent.
- Compatible with in-situ Fmoc removal approach where the deprotection step is carried out immediately after the coupling in the same step to eliminate additional washing step.
- Greener alternative to Piperidine:
- Not a controlled substance
- Effective at lower concentration (2.5% vs 20% of Piperidine)
- Greater stability in green solvent GVL (36% vs 20% remaining after 96h)
- Performs well in multiple green solvent systems
Studies
In-situ Fmoc Removal – A Sustainable Solid-Phase Peptide Synthesis Approach
Ashish Kumar, Anamika Sharma, Beatriz G. de la Torre, Fernando Albericio Green Chem., 2022, 24, 4887.
Ashish Kumar, Anamika Sharma, Beatriz G. de la Torre, Fernando Albericio Green Chem., 2022, 24, 4887.
Efficient Synthesis of Peptides with 4-Methylpiperidine as Fmoc Removal Reagent by Solid Phase Synthesis
Cristian Francisco Vergel Galeano, Zuly Jenny Rivera Monroy, Jaiver Eduardo Rosas Pérez, and Javier Eduardo García Castañedaa, J. Mex. Chem. Soc. 2014, 58(4), 386-392.
Greening Fmoc/tBu solid-phase peptide synthesis
Al Musaimi, Othman and de la Torre, Beatriz G. and Albericio, Fernando, Green Chem. 2020, 22(4) 996-1018