175291-56-2

Usage

Uses

1. Used in Pharmaceutical Industry:
Fmoc-O-(benzylphospho)-L-threonine is used as a building block for the synthesis of phosphothreonine-containing peptides, which are essential components in various biological processes and have potential therapeutic applications.
2. Used in Biochemical Research:
Fmoc-O-(benzylphospho)-L-threonine is used as a synthetic peptide in the synthesis of macrocyclic peptidomimetics, specifically as polo-like kinase 1 polo-box domain-binding inhibitors. These inhibitors play a crucial role in understanding the structure and function of protein-protein interactions and can be used to develop targeted therapies for various diseases.
3. Used in Chemical Synthesis:
Fmoc-O-(benzylphospho)-L-threonine is used as a key intermediate in the synthesis of complex peptides and peptidomimetics, contributing to the development of novel bioactive molecules with potential applications in drug discovery and development.

InChI:InChI=1/C26H26NO8P/c1-17(35-36(31,32)34-15-18-9-3-2-4-10-18)24(25(28)29)27-26(30)33-16-23-21-13-7-5-11-19(21)20-12-6-8-14-22(20)23/h2-14,17,23-24H,15-16H2,1H3,(H,27,30)(H,28,29)(H,31,32)/t17-,24+/m0/s1

Upstream product

• 76101-29-6 benzyloxy dichlorophosphine 
• 100-51-6 benzyl alcohol 
• 73731-37-0 Fmoc-Thr-OH 
• 125760-27-2 N-(9-fluorenylmethyloxycarbonyl)-L-threonine phenacylester 
• 108549-21-9 benzyl-N,N,N',N'-tetraisopropylphosphorodiamidite 
• 175291-55-1 (2S,3R)-3-[Benzyloxy-(2,2,2-trichloro-ethoxy)-phosphoryloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid 2-oxo-2-phenyl-ethyl ester 
• 158171-13-2 benzyl 2,2,2-trichloroethyl diisopropylphosphoramidite 

Downstream Products

• 1190950-23-2 C₆₇H₁₀₂N₁₉O₁₉PS₃ 
• 1256288-02-4 184B-91-1 
• 1610355-13-9 N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-threonine [phenylmethyl hydrogen Phosphate (ester)]phenylmethyl ester 
• 1629149-57-0 benzyl O-[(benzyloxy){[(2,2-dimethylpropanoyl)oxy]methoxy}phosphoryl]-N-{[(9H-fluoren-9-yl)methoxy]carbonyl}-L-threoninate 

Relevant academic research and scientific papers

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.

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.

A general preparation of protected phosphoamino acids

Fmoc-O-benzyl-l-phosphoserine is an important building block in the synthesis of Forigerimod, a phosphopeptide being investigated for Systemic Lupus Erythematosus (SLE). An efficient one-pot process was developed using inexpensive, readily available starting materials. This general procedure was used to prepare a variety of protected phosphoamino acids.

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.