Catalog Number
ACM158171143-1
Product Name
Fmoc-Ser(PO(OBzl)OH)-OH
Description
An excellent building block for the preparation of phosphoserine-containing peptides by Fmoc SPPS. This derivative can be introduced using standard activation methods, such as PyBOPand 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. Applications of this derivative include the preparation of phospholamban , a 52 residue peptide containing both phosphoserine and phosphothreonine, and human salivary statherin, a 42 residue phosphoserine peptide ; for other examples see references.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.
Synonyms
Fmoc-Ser(PO(OBzl)OH)-OH, N-α-Fmoc-O-benzyl-L-phosphoserine
Molecular Formula
C25H24NO8P
InChI
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
InChI Key
ZBPUWGDUVAAWJY-QHCPKHFHSA-N
Application
Peptide synthesis.
Assay
≥90.0% (acidimetric)
≥95.0% (HPLC)
≥97% (TLC)
Reaction Suitability
reaction type: Fmoc solid-phase peptide synthesis
Storage Temperature
-20℃(-15℃to -25℃)
Type
Unusual Amino Acids, Phosphorylated Amino Acids
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