A practical dealkylation procedure for O,O-dimethyl-phosphotyrosyl-containing peptide-resins

Fretz, Heinz

doi:10.1007/bf00127965

Cited by 5 publications

(1 citation statement)

References 48 publications

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“…TMSOTf and dimethylsulfide (DMS) (50% by volume) are added to the mixture to cleave the methyl groups from the phosphate in a trimethylsilyl‐assisted nucleophilic attack of DMS on the methyl groups. Fretz165 studied the de‐methylation of peptides incorporating Tyr(PO 3 Me 2 ) residues in Fmoc‐based synthesis. In these studies, 2.5% DBU was used for Fmoc removal of the phosphotyrosine and subsequent residues to ensure dimethyl protection remained intact.…”

Section: Deprotectionmentioning

confidence: 99%

The synthesis of phosphopeptides

et al. 2001

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Phosphorylation and dephosphorylation are key events in protein expression and regulation and in signal transduction. Phosphopeptides are very useful reagents for the study of these processes, and have been used to great advantage in the study of phosphatase substrate specificity, SH2 domain ligand specificity, and protein–protein interactions. Furthermore, the advent of cell‐permeable peptide carriers, such as those from the antennapedia homeodomain and the HIV TAT transcription factor, has allowed the study of intracellular events, thus underscoring the utility of these reagents. In this paper we review methods for the synthesis of phosphopeptides with the emphasis on the preparation of phosphoamino acid building blocks. © 2001 John Wiley & Sons, Inc. Biopolymers (Pept Sci) 60: 3–31, 2001

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Section: Deprotectionmentioning

confidence: 99%