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158171-14-3 - O-Benzylphospho-N-Fmoc-L-serine, 95% - Fmoc-Ser(PO3BzlH)-OH - H52168 - Alfa Aesar

H52168 O-Benzylphospho-N-Fmoc-L-serine, 95%

CAS Number
158171-14-3
Synonyms
Fmoc-Ser(PO3BzlH)-OH

Size Price ($) Quantity Availability
250mg 63.18
1g 202.50
5g 787.78
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O-Benzylphospho-N-Fmoc-L-serine, 95%

MDL
MFCD00797869

Chemical Properties

Formula
C25H24NO8P
Formula Weight
497.44
Solubility
Slightly soluble in water.

Applications

It can be applied in the synthesis of phosphopeptides. 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. 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 .

Notes

Store away from oxidizing agents. Keep the container tightly closed and place it in a cool, dry and well ventilated condition.

Literature References

Raoul Peltier, et al. Novel Phosphopeptides as Surface-Active Agents in Iron Nanoparticle Synthesis.Australian Journal of Chemistry.,2012,65(6), 680-685.

Dale R. Mowrey, et al. Demonstration of a Scalable One-Pot Synthesis of Fmoc-O-Benzylphospho-l-serine.Org. Process Res. Dev.,2012,16(11), 1861-1865.

Other References

Beilstein
7060483
Harmonized Tariff Code
2931.90
TSCA
No

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