CAS 158171-14-3

Fmoc-O-(benzylphospho)-L-serine

Description:

Fmoc-O-(benzylphospho)-L-serine is a phosphoamino acid derivative commonly used in peptide synthesis and bioconjugation. It features a phenylmethoxycarbonyl (Fmoc) protecting group, which is widely utilized for the protection of amino groups during peptide synthesis. The presence of a benzylphosphoryl group indicates that it contains a phosphonic acid moiety, which can play a crucial role in biological signaling and interactions. This compound is characterized by its ability to participate in various chemical reactions, including phosphorylation and coupling reactions, making it valuable in the development of phosphopeptides. Its structure allows for the introduction of phosphoserine residues into peptides, which can mimic post-translational modifications found in proteins. The compound is typically soluble in organic solvents and may exhibit specific reactivity patterns due to the presence of both the phospho and amino acid functionalities. Overall, Fmoc-O-(benzylphospho)-L-serine serves as an important tool in synthetic organic chemistry and biochemistry for studying protein function and interactions.

Formula: C₂₅H₂₄NO₈P

InChI: InChI=1/C25H24NO8P/c27-24(28)23(16-34-35(30,31)33-14-17-8-2-1-3-9-17)26-25(29)32-15-22-20-12-6-4-10-18(20)19-11-5-7-13-21(19)22/h1-13,22-23H,14-16H2,(H,26,29)(H,27,28)(H,30,31)/t23-/m0/s1

SMILES: c1ccc(cc1)COP(=O)(O)OC[C@@H](C(=O)O)N=C(O)OCC1c2ccccc2c2ccccc12

Synonyms:

• Fmoc-L-Ser(Po(Obzl)Oh)
• Fmoc-L-Ser(Po(Obzl)Oh)-Oh
• Fmoc-L-Phosphoserine
• Fmoc-O-Benzyl-L-Phosphoserine
• Fmoc-Ser(Po(Obzl)Oh)-Oh
• Fmoc-Ser(HPO3Bzl)-OH
• Fmoc-Serine(Po(Obzl)Oh)-Oh
• O-[(benzyloxy)(hydroxy)phosphoryl]-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-serine
• Fmoc-Ser(PO(OBzl))-OH

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

CAS: 158171-14-3

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

Formula: C₂₅H₂₄NO₈P

Purity: 95%

Molecular weight: 497.44

Ref: 02-H52168

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

CAS: 158171-14-3

Building block for the synthesis of phosphoserine-containing peptides. Harris et al. observed a considerable extent of S-benzylation of adjacent Met residues during microwave-assisted TFA cleavage. Attard et al. recommend the use of cyclohexylamine/DCM (1:1) for Fmoc removal to minimize concomitant β-elimination.

Formula: C₂₅H₂₄NO₈P

Purity: 97.96%

Color and Shape: White Powder

Molecular weight: 497.44

Ref: 01-4029345

L-Serine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-O-[hydroxy(phenylmethoxy)phosphinyl]-

CAS: 158171-14-3

Formula: C₂₅H₂₄NO₈P

Purity: 97%

Color and Shape: Solid

Molecular weight: 497.4337

Ref: IN-DA001Q0N

Fmoc-Ser(PO3BzlH)-OH

CAS: 158171-14-3

Formula: C₂₅H₂₄NO₈P

Purity: ≥ 97.0%

Color and Shape: Off-white powder

Molecular weight: 497.44

Ref: 7W-GM3202

Fmoc-O-(Benzylphospho)-L-Serine

CAS: 158171-14-3

Fmoc-O-(Benzylphospho)-L-Serine

Purity: 98%

Molecular weight: 497.43g/mol

Ref: 54-OR1013380

Fmoc-O-benzylphospho-L-serine

CAS: 158171-14-3

Fmoc-O-benzylphospho-L-serine is a fmoc-protected phosphoserine derivative for efficient synthesis of phosphoserine-containing peptides via standard fmoc SPPS. Compatible with common activators such as PyBOP or TBTU, it remains stable during piperidine deprotection and enables incorporation of multiple phosphoserine residues, for example successful syntheses of phospholamban and human salivary statherin. In certain cases,  β-piperidinylalanine formation may occur during N-terminal Ser(PO(OBzl)OH) Fmoc deprotection, especially under microwave conditions.

Formula: C₂₅H₂₄NO₈P

Purity: Min. 97 Area-%

Color and Shape: White Off-White Powder

Molecular weight: 497.43 g/mol

Ref: 3D-FF47773

Fmoc-Ser(HPO3Bzl)-OH

CAS: 158171-14-3

M03387 - Fmoc-Ser(HPO3Bzl)-OH

Formula: C₂₅H₂₄NO₈P

Purity: 95%

Color and Shape: Powder

Molecular weight: 497.44

Ref: 10-M03387