Compatibility Study of Merrifield Linker in Fmoc Strategy Peptide Synthesis

Title:Compatibility Study of Merrifield Linker in Fmoc Strategy Peptide Synthesis

Volume: 20 Issue: 2

Author(s): Xiaoxiao Yang, Hao Lin, Wen Lu and Dexin Wang

Affiliation:

Keywords: Merrifield linker, Fmoc strategy, peptide synthesis, aminolysis, hydrolysis

Abstract: The stability of Merrifield linker in Fmoc deprotection process was quantitatively investigated by establishing working curve of two major decomposition components from two resin bound dipeptide models. By sampling reaction solution and analyzing with RP-HPLC, decomposition rate was determined. The results indicated that either α-amino acid or β-amino acid anchored Merrifield linker was endurable for Fmoc strategy peptide synthesis in common de-Fmoc conditions such as 20% piperidine/DMF and 2% DBU/2% piperidine/DMF under room temperature treatments. However, Fmoc-deprotection with microwave assistance of α-amino acid anchored peptide resin with 20% piperidine/DMF more than 20 times or β-amino acid anchored peptide resin with 2% DBU/2% piperidine/DMF more than 30 times is not recommended. Feasibility of the proposed compatibility was verified by design and synthesis of a thymic humoral factor derived peptide via Fmoc strategy on Merrifield resin. Thus by choosing moderate de-Fmoc protocol, Merrifield resin is feasible for Fmoc strategy oligopeptide synthesis.

Cite this article as:

Yang Xiaoxiao, Lin Hao, Lu Wen and Wang Dexin, Compatibility Study of Merrifield Linker in Fmoc Strategy Peptide Synthesis, Protein & Peptide Letters 2013; 20 (2) . https://dx.doi.org/10.2174/0929866511320020004