Analysis Note

Colour (visual): white to slight yellow to beigeAppearance of substance (visual): powderIdentity (IR): passes testEnantiomeric purity: ≥ 99.0 % (a/a)Purity (TLC(CMA1)): ≥ 97 %Assay (HPLC, area%): ≥ 95.0 % (a/a)Solubility (1 mmole in 2 ml DMF): clearly solubleAssay (acidimetric): ≥ 90.0 %Water (K. F.): ≤ 1.0 %Ethyl acetate (HS-GC): ≤ 0.5 ¬etate (IC): ≤ 0.1 %For TLC-Systems see our General Catalog

General description

An excellent building block for the preparation of phosphoserine-containing peptides [1]. This derivative can be introduced using standard activation methods, such as PyBOP^® and TBTU. The monoprotected phosphoserine residue once incorporated is stable to piperidine. Using this reagent, even peptides containing multiple phosphorylation sites can be prepared efficiently by standard Fmoc SPPS methods [2].

Applications of this derivative include the preparation of phospholamban [3], a 52 residue peptide containing both phosphoserine and phosphothreonine, and human salivary statherin, a 42 residue phosphoserine peptide [4]; for other examples see references [5-8].

Recently, β-piperidinylalanine formation has been shown to occur during Fmoc deprotection of N-terminal Ser(PO(OBzl)OH), particularly under microwave conditions. This side reaction can be eliminated by using cyclohexylamine or DBU just for this Fmoc deprotection step [9].

The product number for this product was previously 04-12-1154.

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Legal Information

PyBOP is a registered trademark of Merck KGaA, Darmstadt, Germany

Novabiochem is a registered trademark of Merck KGaA, Darmstadt, Germany

Linkage

Replaces: 04-12-1154