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Updated: Jan 12, 2026
Solid Phase Synthesis of a Functionalized Bis-Peptide Using "Safety Catch" Methodology
Published on: May 15, 2012
Deprotection Bases as an Alternative to the Traditional Bases Used in Solid-Phase Peptide Synthesis
Maria Carolina Oliveira de Arruda Brasil1, Cleverson Rogerio Princival2, Vinicius Kuchenbecker2
1Laboratory of Synthesis and Studies of Biomolecules, Department of Biochemistry and Organic Chemistry, São Paulo State University (UNESP), Institute of Chemistry, Araraquara/SP, Brazil.
Background:
The use of peptides in the pharmaceutical and cosmetic industries is attracting increasing attention. Most of the peptides currently marketed are obtained by chemical processes, most frequently solid-phase peptide synthesis (SPPS).
Objective:
Although SPPS is efficient, it requires hazardous solvents, such as N,N-dimethylformamide, dichloromethane, and N-methylpyrrolidone, as well as the bases piperidine and 4-methylpiperidine in the deprotection step. This study presents two alternative reagents, 2-aminoethanol and 2-amino-2-methyl-1- propanol, for the removal of the fluorenyl-methyloxycarbonyl protecting group used in SPPS.
Methods:
The traditional and alternative green SPPS using Fmoc protocol were employed.
Results:
The synthesis of two peptides showed that the 2-aminoethanol and 2-amino-2-methyl-1-propanol are viable replacements for piperidine-derived reagents in peptide synthesis.
Discussion:
The use of these reagents in SPPS afforded two peptides in high yield in an environmentally sustainable solvent.
Conclusion:
The reagents are thus promising alternatives to piperidine derivatives, particularly 2-amino- 2-methyl-1-propanol, in SPPS.
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