8.52069

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

≥97% (TLC), for peptide synthesis, Novabiochem^®

• Synonym(s): Fmoc-Ser(PO(OBzl)OH)-OH, N-α-Fmoc-O-benzyl-L-phosphoserine
• Empirical Formula (Hill Notation): C₂₅H₂₄NO₈P
• CAS Number: 158171-14-3
• Molecular Weight: 497.43
• UNSPSC Code: 12352209
• NACRES: NA.22
• MDL number: MFCD00797869

Properties

• Product Name: Fmoc-Ser(PO(OBzl)OH)-OH, Novabiochem^®
• Quality Segment: 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)
• SMILES string: [P](=O)(OC[C@H](NC(=O)OCC2c3c(cccc3)c4c2cccc4)C(=O)O)(OCc1ccccc1)O
• 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

Description

General description

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.

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.

Other Notes

Replaces: 04-12-1154

Legal Information

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

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

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable