Lanthanide-mediated dephosphorylation used for peptide cleavage during solid phase peptide synthesis

Byunghee Yoo, Mark "Marty" Pagel

Research output: Contribution to journalArticle

3 Citations (Scopus)

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.

Original languageEnglish (US)
Pages (from-to)3894-3905
Number of pages12
JournalMolecules
Volume18
Issue number4
DOIs
StatePublished - Apr 2013

Fingerprint

Lanthanoid Series Elements
Solid-Phase Synthesis Techniques
peptides
solid phases
cleavage
Peptides
Ions
synthesis
ions
Hydrolysis
Phosphates
resins
Temperature
Acids
hydrolysis
phosphates
Resins
methodology
chemistry
aqueous solutions

Keywords

  • Dephosphorylation
  • Lanthanide
  • Peptide synthesis
  • Solid phase

ASJC Scopus subject areas

  • Organic Chemistry
  • Medicine(all)

Cite this

Lanthanide-mediated dephosphorylation used for peptide cleavage during solid phase peptide synthesis. / Yoo, Byunghee; Pagel, Mark "Marty".

In: Molecules, Vol. 18, No. 4, 04.2013, p. 3894-3905.

Research output: Contribution to journalArticle

@article{78f3ce32333f4565bf41bf7dea7094cd,
title = "Lanthanide-mediated dephosphorylation used for peptide cleavage during solid phase peptide synthesis",
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 = "Dephosphorylation, Lanthanide, Peptide synthesis, Solid phase",
author = "Byunghee Yoo and Pagel, {Mark {"}Marty{"}}",
year = "2013",
month = "4",
doi = "10.3390/molecules18043894",
language = "English (US)",
volume = "18",
pages = "3894--3905",
journal = "Molecules",
issn = "1420-3049",
publisher = "Multidisciplinary Digital Publishing Institute (MDPI)",
number = "4",

}

TY - JOUR

T1 - Lanthanide-mediated dephosphorylation used for peptide cleavage during solid phase peptide synthesis

AU - Yoo, Byunghee

AU - Pagel, Mark "Marty"

PY - 2013/4

Y1 - 2013/4

N2 - 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.

AB - 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.

KW - Dephosphorylation

KW - Lanthanide

KW - Peptide synthesis

KW - Solid phase

UR - http://www.scopus.com/inward/record.url?scp=84876757547&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84876757547&partnerID=8YFLogxK

U2 - 10.3390/molecules18043894

DO - 10.3390/molecules18043894

M3 - Article

C2 - 23549296

AN - SCOPUS:84876757547

VL - 18

SP - 3894

EP - 3905

JO - Molecules

JF - Molecules

SN - 1420-3049

IS - 4

ER -