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

CAS: 158171-14-3 | C25H24NO8P | 497.44 g/mol

$148.45 - $1837.68

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
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AAH52168MD
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Thermo Scientific Chemicals
H52168MD
250 mg
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AAH5216803
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Thermo Scientific Chemicals
H5216803
1 g
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AAH5216806
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Thermo Scientific Chemicals
H5216806
5 g
Each for $1,837.68
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Description

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

158171-14-3
497.44
ZBPUWGDUVAAWJY-QHCPKHFHSA-N
11005563
C1=CC=C(C=C1)COP(=O)(O)OCC(C(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24
C25H24NO8P
MFCD00797869
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
(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[hydroxy(phenylmethoxy)phosphoryl]oxypropanoic acid

Specifications

158171-14-3
MFCD00797869
7060483
Slightly soluble in water.
C1=CC=C(C=C1)COP(=O)(O)OCC(C(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24
497.44
497.44
O-Benzylphospho-N-Fmoc-L-serine
C25H24NO8P
250 mg
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
ZBPUWGDUVAAWJY-QHCPKHFHSA-N
(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[hydroxy(phenylmethoxy)phosphoryl]oxypropanoic acid
11005563
95%
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Safety and Handling

Safety and Handling

TSCA : No

Recommended Storage : Ambient temperatures

SDS
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RUO – Research Use Only