Fmoc-O-(benzylphospho)-L-serine Chemical Properties

Density 

1.403±0.06 g/cm3(Predicted)

storage temp. 

Store at -15°C to -25°C.

solubility 

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

form 

Powder

pka

1.42±0.50(Predicted)

color 

White to off-white

Water Solubility 

Slightly soluble in water.

BRN 

7060483

InChIKey

ZBPUWGDUVAAWJY-QHCPKHFHSA-N

SMILES

C(O)(=O)[C@H](COP(O)(OCC1=CC=CC=C1)=O)NC(OCC1C2=C(C=CC=C2)C2=C1C=CC=C2)=O

CAS DataBase Reference

158171-14-3(CAS DataBase Reference)

Safety Information

WGK Germany 

3

F 

10-21

HS Code 

2924 29 70

MSDS

• Language:English Provider:SigmaAldrich

Fmoc-O-(benzylphospho)-L-serine Usage And Synthesis

Chemical Properties

White to off-white powder

Uses

Building block for the synthesis of phosphoserine containing peptides.

Uses

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 .

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

Fmoc-O-(benzylphospho)-L-serine(158171-14-3)Related Product Information

• DL-Serine
• Benzyl acetate
• Benzyl chloroformate
• Benzyltriethylammonium chloride
• 9-Fluorenylmethyl chloroformate
• Nalpha-Fmoc-Ndelta-trityl-L-glutamine
• Benzyl carbamate
• Benzyl benzoate
• Fmoc-L-Serine
• L-Homoserine
• L-Serine
• Benzyl propionate
• L-ALPHA-PHOSPHATIDYLSERINES, BRAIN, BOVINE
• Fmoc-Phe-OH
• D-Cycloserine
• Fmoc-Lys(Boc)-OH
• Fmoc-OSu
• Dibenzyl phosphate