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

Chemical Properties

White to off-white powder

Uses

Different sources of media describe the Uses of 158171-14-3 differently. You can refer to the following data:
1. Building block for the synthesis of phosphoserine containing peptides.
2. 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 .

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

• 100-51-6 benzyl alcohol 
• 76101-29-6 benzyloxy dichlorophosphine 
• 158171-13-2 benzyl 2,2,2-trichloroethyl diisopropylphosphoramidite 
• 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.