4210-66-6

Basic information

• Product Name: (2S)-2-amino-4-phosphonooxy-butanoic acid
• Synonyms: (2S)-2-amino-4-phosphonooxy-butanoic acid;O-Phosphohomoserine;H-Hse(PO3H2)-OH;L-2-Amino-4-hydroxybutyric acid 4-phosphate lithium salt;L-Homoserine O-phosphate lithium salt;O-Phospho-L-homoserine lithium salt;O-Phosphono-L-homoserine lithium salt;Homoserine phosphate
• CAS NO: 4210-66-6
• Molecular Formula: C₄H₁₀NO₆P
• Molecular Weight: 199.0991
• Mol File: 4210-66-6.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 502.3°Cat760mmHg
• Flash Point: 257.6°C
• Appearance: /
• Density: 1.676g/cm³
• Vapor Pressure: 1.87E-11mmHg at 25°C
• Refractive Index: 1.541
• Storage Temp.: ?20°C
• CAS DataBase Reference: (2S)-2-amino-4-phosphonooxy-butanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2S)-2-amino-4-phosphonooxy-butanoic acid(4210-66-6)
• EPA Substance Registry System: (2S)-2-amino-4-phosphonooxy-butanoic acid(4210-66-6)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 4210-66-6(Hazardous Substances Data)

Usage

Definition

ChEBI: The L-enantiomer of O-phosphohomoserine.

InChI:InChI=1/C4H10NO6P/c5-3(4(6)7)1-2-11-12(8,9)10/h3H,1-2,5H2,(H,6,7)(H2,8,9,10)/t3-/m0/s1

Synthetic route

(S)-2-Benzyloxycarbonylamino-4-(diphenoxy-phosphoryloxy)-butyric acid 4-nitro-benzyl ester (55596-52-6) → L-2-amino-4-phosphonobutyric acid (4210-66-6)

Conditions	Yield
With hydrogen; platinum(IV) oxide In acetic acid

(S)-2-Amino-4-(diphenoxy-phosphoryloxy)-butyric acid benzyl ester → L-2-amino-4-phosphonobutyric acid (4210-66-6)

Conditions	Yield
With hydrogen; platinum on activated charcoal In acetic acid

(S)-4-Phosphonooxy-2-(2,2,2-trifluoro-acetylamino)-butyric acid isopropyl ester → L-2-amino-4-phosphonobutyric acid (4210-66-6)

Conditions	Yield
With potassium hydroxide In ethanol at 20℃; for 3h; Yield given;
With potassium hydroxide In ethanol at 20℃; for 3h; Yield given;

L-2-amino-4-phosphonobutyric acid (4210-66-6) → L-threonine (72-19-5)

Conditions	Yield
With perchloric acid; ethylenediaminetetraacetic acid; potassium chloride; 2,2'-piperazine-1,4-diyl-bis-ethanesulfonic acid at 24.84℃; pH=8; Kinetics; Concentration; Enzymatic reaction;
With pyridoxal 5'-phosphate; threonine synthase from Bacillus subtilis In aq. phosphate buffer at 37℃; for 2h; pH=7.5; Reagent/catalyst; Enzymatic reaction;

Upstream product

• 55596-52-6 (S)-2-Benzyloxycarbonylamino-4-(diphenoxy-phosphoryloxy)-butyric acid 4-nitro-benzyl ester 

Downstream Products

• 72-19-5 L-threonine 

Relevant articles and documents

Synthesis of (2S)-O-phosphohomoserine and its C-2 deuteriated and C-3 chirally deuteriated isotopomers: Probes for the pyridoxal phosphate-dependent threonine synthase reaction

A short efficient synthesis of the threonine synthase substrate (2S)-O-phosphohomoserine and its C-2 deuteriated and C-3 chirally deuteriated isotopomers is described. The synthetic route also provides access to (2S)-homoserine and its C-2 deuteriated and C-3 chirally deuteriated isotopomers in high yield. Preliminary deuterium isotope effect determinations performed using the deuteriated (2S)-O-phosphohomoserines and threonine synthase from E. coli indicate that the removal of protons from both C-2 and C-3 is kinetically important.

Improved synthesis of o-phosphohomoserine.

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