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Lanthanide-mediated dephosphorylation used for peptide cleavage during solid phase peptide synthesis
1MGH/MIT/HMS Athinoula A. Martinos Center for Biomedical Imaging, Massachusetts General Hospital and Harvard Medical School, Boston, MA 02129, USA. byunghee@nmr.mgh.harvard.edu
Molecules (Basel, Switzerland)
|April 4, 2013
Summary
Lanthanide ions offer a mild, neutral method to cleave phosphorylated supports in solid phase peptide synthesis (SPPS). This approach preserves side-chain protecting groups, enabling efficient peptide synthesis and orthogonal cleavage.
Area of Science:
- Organic Chemistry
- Biochemistry
- Materials Science
Background:
- Lanthanide(III) ions catalyze phosphomonoester and phosphodiester hydrolysis in neutral solutions.
- Solid phase peptide synthesis (SPPS) requires efficient and orthogonal cleavage methods.
Purpose of the Study:
- To develop and validate lanthanide-mediated dephosphorylation as a mild, orthogonal cleavage condition for SPPS.
- To synthesize peptides using a novel phosphorylated polymeric support and lanthanide cleavage.
Main Methods:
- Development of a Boc-chemistry-based phosphorylated polymeric support for SPPS.
- Investigation of resin-bound phosphate cleavage using various lanthanide ions (Eu(III), Yb(III)), conditions (acid, base, solvents, temperature).
- Synthesis and cleavage of a model peptide sequence using lanthanide ions in neutral aqueous media.
Main Results:
- Lanthanide ions effectively mediated the cleavage of resin-bound phosphates in neutral aqueous media.
- The developed method demonstrated orthogonality, retaining side-chain protecting groups during cleavage.
- A peptide sequence was successfully synthesized and cleaved using this novel approach.
Conclusions:
- Lanthanide-mediated dephosphorylation presents a mild and orthogonal cleavage strategy for SPPS.
- This methodology simplifies SPPS by enabling cleavage under neutral aqueous conditions.
- The developed phosphorylated support and cleavage method show significant utility in peptide synthesis.
