158171-14-3

Basic information

• Product Name: Fmoc-O-(benzylphospho)-L-serine
• Synonyms: Fmoc-Ser(PO3BzlH)-OH, >=98%;Fmoc-L-Ser(HPO3Bzl)-OH;Fmoc-O-benzylphospho-L-serine≥ 97% (HPLC);Fmoc-Ser(PO(OBzl)OH)-OH Novabiochem;FMOC-L-SER(PO(OBZL)OH);FMOC-L-SER(PO(OBZL)OH)-OH;FMOC-L-PHOSPHOSERINE;FMOC-O-BENZYL-L-PHOSPHOSERINE
• CAS NO: 158171-14-3
• Molecular Formula: C₂₅H₂₄NO₈P
• Molecular Weight: 497.43
• Product Categories: Unusual amino acids;Serine [Ser, S];Fmoc-Amino Acids and Derivatives;Fmoc-Amino acid series;a-amino;amino acids
• Mol File: 158171-14-3.mol
• Article Data: 6

Chemical Properties

• Appearance: white powder
• Density: 1.403 g/cm³
• Refractive Index: 1.622
• Storage Temp.: 2-8°C
• PKA: 1.42±0.50(Predicted)
• Water Solubility: Slightly soluble in water.
• BRN: 7060483
• CAS DataBase Reference: Fmoc-O-(benzylphospho)-L-serine(CAS DataBase Reference)
• NIST Chemistry Reference: Fmoc-O-(benzylphospho)-L-serine(158171-14-3)
• EPA Substance Registry System: Fmoc-O-(benzylphospho)-L-serine(158171-14-3)

Safety Data

• WGK Germany: 3
• F: 10-21
• Hazardous Substances Data: 158171-14-3(Hazardous Substances Data)

Usage

Description

Fmoc-O-(benzylphospho)-L-serine is a synthetic amino acid derivative used in the field of organic chemistry and peptide synthesis. It is a white to off-white powder and serves as a crucial building block for the creation of phosphoserine-containing peptides. Fmoc-O-(benzylphospho)-L-serine is particularly valuable in the development of phosphopeptides, which play a significant role in various biological processes and are essential for understanding cellular signaling pathways.

Uses

Used in Peptide Synthesis:
Fmoc-O-(benzylphospho)-L-serine is used as a building block for the synthesis of phosphoserine-containing peptides. Its incorporation into peptide sequences allows for the study of phosphorylation events, which are critical for regulating protein function and cellular signaling.
Used in Pharmaceutical Research:
In the pharmaceutical industry, Fmoc-O-(benzylphospho)-L-serine is used as a key component in the development of phosphopeptides. These peptides can be employed as therapeutic agents or as tools for understanding the role of phosphorylation in various diseases, including cancer and neurological disorders.
Used in Chemical Synthesis:
Fmoc-O-(benzylphospho)-L-serine can be applied in the synthesis of phosphopeptides using standard activation methods, such as PyBOP and TBTU. The monoprotected phosphoserine residue, once incorporated, is stable to piperidine, enabling the efficient preparation of peptides containing multiple phosphorylation sites through standard Fmoc SPPS methods.
Used in Research Laboratories:
In academic and research settings, Fmoc-O-(benzylphospho)-L-serine is used as a reagent for studying the effects of phosphorylation on protein structure and function. It also aids in the development of novel drug delivery systems and the investigation of protein-protein interactions.

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

Upstream product

• 158171-13-2 benzyl 2,2,2-trichloroethyl diisopropylphosphoramidite 
• 100-51-6 benzyl alcohol 
• 76101-29-6 benzyloxy dichlorophosphine 
• 73724-45-5 N-(9H-fluoren-9-ylmethoxycarbonyl)-L-serine 
• 108549-21-9 benzyl-N,N,N',N'-tetraisopropylphosphorodiamidite 
• 125760-26-1 N-Fmoc serine phenacyl ester 
• 175291-54-0 Fmoc-Ser-OPac 

Downstream Products

• 407-41-0 L-phosphoserine 
• 1400869-96-6 C₇₂H₁₁₄N₂₅O₂₁P 
• 1400869-94-4 C₇₁H₁₁₂N₂₅O₂₁P 
• 1142403-38-0 Fmoc-O-benzyloxy-phosphono-L-serine cyclohexyl amide 
• 865470-64-0 H-Tyr-Ser(PO₃H₂)-Phe-OH 
• 158171-17-6 {(S)-2-(Benzyloxy-hydroxy-phosphoryloxy)-1-[(S)-1-(di-p-tolylmethyl-carbamoyl)-ethylcarbamoyl]-ethyl}-carbamic acid 9H-fluoren-9-ylmethyl ester 

Relevant articles and documents

Demonstration of a scalable one-pot synthesis of Fmoc-O-benzylphospho-l- serine

A cost-effective one-pot synthesis of Fmoc-O-benzylphospho-l-serine, an amino acid commonly used in the synthesis of phosphorylated peptides, has been developed. Two methods for executing this synthesis are described, and both have been scaled to provide kilogram quantities of the title compound in ～50% isolated yield. Development of both processes has led to the identification of crystallization conditions which provide the product as a solvate with high purity. An efficient process for generating the solvent-free product from the solvate has also been developed.

PROCESS FOR PREPARING PHOSPHORYLATED AMINO ACIDS

The present invention provides a short, safe, inexpensive, commercially scalable process for preparing a phosphorylated amino acid of Formula I, which can be performed in one pot without isolating any synthetic intermediates.

Preparations of Nα-Fmoc-O-[(benzyloxy)hydroxyphosphinyl] β-hydroxy α-amino acid derivatives

Nα-Fmoc-O-[(benzyloxy)hydroxyphosphinyl]serine and Nα-Fmoc-O-[(benzyloxy)hydroxyphosphinyl]threonine were prepared in order to be utilized for the synthesis of phosphoserine- or phosphothreonine-containing peptides based on the Fmoc-mode pre-phosphorylation strategy. These derivatives were obtained as crystalline compounds, which are favorable for use as building blocks for an automated peptide synthesis by a solid-phase method.