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 ArticlesCleavage 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.
