O-Benzylphospho-N-Fmoc-L-serine, 95%, Thermo Scientific Chemicals

Description

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 .

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

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 .

Solubility
Slightly soluble in water.

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

Specifications

Chemical Identifiers

• CAS: 158171-14-3
• Molecular Formula: C25H24NO8P
• Molecular Weight (g/mol): 497.44
• MDL Number: MFCD00797869
• InChI Key: ZBPUWGDUVAAWJY-QHCPKHFHSA-N
• Synonym: fmoc-o-benzylphospho-l-serine, fmoc-ser hpo3bzl-oh, fmoc-o-benzyl-l-phosphoserine, fmoc-ser po3bzlh-oh, 2s-2-9h-fluoren-9-yl methoxy carbonyl amino-3-benzyloxy hydroxy phosphoryl oxy propanoic acid, 2s-3-benzyloxy hydroxy phosphoryl oxy-2-9h-fluoren-9-ylmethoxy carbonyl amino propanoic acid, pubchem20516, fmoc-l-ser po obzl oh-oh, n-fmoc-o-benzylphospho-l-serine, fmoc-ser po3bzlh-oh hplc
• PubChem CID: 11005563
• IUPAC Name: (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[hydroxy(phenylmethoxy)phosphoryl]oxypropanoic acid
• SMILES: C1=CC=C(C=C1)COP(=O)(O)OCC(C(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24

• Quantity: 1 g
• Beilstein: 7060483
• Solubility Information: Slightly soluble in water.
• Formula Weight: 497.44
• Percent Purity: 95%
• Chemical Name or Material: O-Benzylphospho-N-Fmoc-L-serine

RUO – Research Use Only