Fmoc-Ser(PO(OBzl)OH)-OH

C₂₅H₂₄NO₈P

497.43

MFCD00797869

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.

To obtain a certificate of analysis (CoA) of a lot that begins with the letter “A”, please select the option in the right hand menu “Request a COA for Lot#s starting with A”.

Replaces: 04-12-1154

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

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

200

Novabiochem^®

≥90.0% (acidimetric)
≥95.0% (HPLC)
≥97% (TLC)

powder

reaction type: Fmoc solid-phase peptide synthesis

Novabiochem^®

peptide synthesis

Fmoc

15-25℃

1S/C25H24NO8P/c27-24(28)23(16-34-35(30,31)33-14-17-8-2-1-3-9-17)26-25(29)32-15-22-20-12-6-4-10-18(20)19-11-5-7-13-21(19)22/h1-13,22-23H,14-16H2,(H,26,29)(H,27,28)(H,30,31)/t23-/m0/s1

ZBPUWGDUVAAWJY-QHCPKHFHSA-N

11 - Combustible Solids

WGK 3