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852069 Fmoc-Ser(PO(OBzl)OH)-OH

Fmoc-Ser(PO(OBzl)OH)-OH Novabiochem®. CAS 158171-14-3, molar mass 497.45 g/mol.

Fmoc-Ser(PO(OBzl)OH)-OH MSDS (material safety data sheet) or SDS, CoA and CoQ, dossiers, brochures and other available documents.
CAS #: 158171-14-3 Molar Mass: 497.44 g/mol Hill Formula: C₂₅H₂₄NO₈P
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Overview

Replacement Information

Key Spec Table

CAS #Hill FormulaMolar Mass
158171-14-3C₂₅H₂₄NO₈P497.44 g/mol
Description
Catalogue Number852069
Replaces04-12-1154
Brand Family Novabiochem®
Alternate Names
  • N-α-Fmoc-O-benzyl-L-phosphoserine
Background InformationAn excellent building block for the preparation of phosphoserine-containing peptides [1]. 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 [5-8].

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].

The product number for this product was previously 04-12-1154.

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References
Product Information
CAS number158171-14-3
Hill FormulaC₂₅H₂₄NO₈P
Molar Mass497.44 g/mol
HS Code2924 29 99
Structure formula ImageStructure formula Image
Quality LevelMQ200
Applications
ApplicationFmoc-Ser(PO(OBzl)OH)-OH Novabiochem®. CAS 158171-14-3, molar mass 497.45 g/mol.
Biological Information
Physicochemical Information
Dimensions
Materials Information
Toxicological Information
Safety Information according to GHS
Storage class10 - 13 Other liquids and solids
WGKWGK 3 highly hazardous to water
Safety Information
Product Usage Statements
Storage and Shipping Information
StorageStore at -15°C to -25°C.
Packaging Information
Transport Information
Supplemental Information
Specifications
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 %
For TLC-Systems see our General Catalog

Documentation

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

Title

Safety Data Sheet (SDS) 

Citations

Title
  • [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.