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

An excellent building block for the preparation of phosphoserine-containing peptides ^[1] by Fmoc SPPS. 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 ^[5,6,7,8].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].

Associated Protocols and Technical Articles
Cleavage and Deprotection Protocols for Fmoc SPPS


Literature references

^[1] T. Wakamiya, et al. (1994) Chem. Lett., 1099.
^[2] P. White & J. Beythien in ′Innovations & Perspectives in Solid Phase Synthesis and Combinatorial Libraries, 4th International Symposium′, Mayflower Scientific Ltd., Birmingham, 1996, pp. 557.
^[3] H. Schmid, et al., Poster 423 presented at the 15th American Peptide Symposium, Nashville, 1997.
^[4] T. L. Gururaja & M. J. Levine (1996) Pept. Res., 9, 283.
^[5] T. Vorherr, et al. (1995) Bioorg. Med. Chem. Lett., 5, 2661.
^[6] G. Shapiro, et al. (1996) Bioorg. Med. Chem. Lett., 6, 409.
^[7] M. John, et al. (1996) Pept. Res., 9, 71.
^[8] K. Teruya, et al. (2004) J. Pept. Sci., 10, 479.
^[9] T. J. Attard, et al. (2009) Int. J. Pept. Res. Ther., 15, 69.

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 %

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