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Molecules 2013, 18(4), 3894-3905; doi:10.3390/molecules18043894
Article

Lanthanide-Mediated Dephosphorylation Used for Peptide Cleavage during Solid Phase Peptide Synthesis

1
 and 2,†,*
1 MGH/MIT/HMS Athinoula A. Martinos Center for Biomedical Imaging, Massachusetts General Hospital and Harvard Medical School, Boston, MA 02129, USA 2 Departments of Chemistry & Biochemistry, Biomedical Imaging and Medical Imaging, University of Arizona, Tucson, AZ 85724, USA Current Address: University of Arizona Cancer Center, 1515 N. Campbell Ave., Tucson, AZ 85724, USA.
* Author to whom correspondence should be addressed.
Received: 28 January 2013 / Revised: 27 February 2013 / Accepted: 27 March 2013 / Published: 2 April 2013
(This article belongs to the Special Issue Chemical Protein and Peptide Synthesis)
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Abstract

Lanthanide(III) ions can accelerate the hydrolysis of phosphomonoesters and phosphodiesters in neutral aqueous solution. In this paper, lanthanide-mediated dephosphorylation has been applied in aqueous media as an orthogonal cleavage condition that can be employed in conventional solid phase peptide synthesis (SPPS). A phosphorylated polymeric support for SPPS was developed using Boc chemistry. The cleavage of resin-bound phosphates was investigated with the addition of Eu(III), Yb(III), acid or base, a mixture of solvents or different temperatures. To demonstrate the utility of this approach for SPPS, a peptide sequence was synthesized on a phosphorylated polymeric support and quantitatively cleaved with lanthanide ions in neutral aqueous media. The protecting groups for side chains were retained during peptide cleavage using lanthanide ions. This new methodology provides a mild orthogonal cleavage condition of phosphoester as a linker during SPPS.
Keywords: lanthanide; dephosphorylation; peptide synthesis; solid phase lanthanide; dephosphorylation; peptide synthesis; solid phase
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Yoo, B.; Pagel, M.D. Lanthanide-Mediated Dephosphorylation Used for Peptide Cleavage during Solid Phase Peptide Synthesis. Molecules 2013, 18, 3894-3905.

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