4210-66-6

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 academic research and scientific papers

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.

Synthesis of L-O-Phosphohomoserine and its C-3 Chirally Deuteriated Isotopomers: Probes for the Pyridoxal Phosphate Dependent Threonine Synthase Reaction

A short efficient synthesis of the threonine synthase substrate L-O-phosphohomoserine and its C-3 chirally deuteriated isotopomers is described; the route also provides access to L-homoserine and its C-3 chirally deuteriated isotopomers in high yield.