Sigma-Aldrich Fmoc-Ser(PO(Obzl)Oh)-Oh 1

Quality Level

200

Product Line

Novabiochem^®

Assay

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

Form

powder

Reaction Suitability

reaction type: Fmoc solid-phase peptide synthesis

Manufacturer/Tradename

Novabiochem^®

Application(S)

peptide synthesis

Functional Group

Fmoc

Storage Temp.

−20°C (−15°C to −25°C)

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

Related Categories

Amino Acids, Resins & Reagents for Peptide Synthesis

General 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 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 . 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 ^[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

T. Wakamiya,et Al. (1994)Chem. Lett., 1099.
P. White & J. Beythien in ′Innovations & Perspectives in Solid Phase Synthesis and Combinatorial Libraries, 4th International Symposium′, Mayflower Scientific Ltd., Birmingham, 1996, PP. 557.
H. Schmid, et Al., Poster 423 presented at the 15th American Peptide Symposium, Nashville, 1997.
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.

Linkage

Replaces: 04-12-1154

Analysis Note

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 %

To see the solvent systems used for TLC of Novabiochem^®products please click here.Novabiochem is a registered trademark of Merck KGaA, Darmstadt, GermanyPyBOP is a registered trademark of Merck KGaA, Darmstadt, Germany