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Literature summary extracted from

  • Sachpatzidis, A.; Dealwis, C.; Lubetsky, J.B.; Liang, P.H.; Anderson, K.S.; Lolis, E.
    Crystallographic studies of phosphonate-based alpha-reaction transition-state analogues complexed to tryptophan synthase (1999), Biochemistry, 38, 12665-12674.
    View publication on PubMed

Application

EC Number Application Comment Organism
4.2.1.20 biotechnology enzyme is a target for structure-based design of herbicides Salmonella enterica subsp. enterica serovar Typhimurium

Crystallization (Commentary)

EC Number Crystallization (Comment) Organism
4.2.1.20 purified recombinant enzyme in complex with potential alpha-reaction phosphonate inhibitors, 5-10 mg/ml protein mixed with 1 mM inhibitor, in 50 mM bicine, 1 mM Na-EDTA, 0.8-1.5 mM spermine, 12% PEG 4000, to pH 7.8 with NaOH, X-ray diffraction structure determination and analysis at 2.3 A resolution or higher Salmonella enterica subsp. enterica serovar Typhimurium

Inhibitors

EC Number Inhibitors Comment Organism Structure
4.2.1.20 4-(2-aminophenylthio)butylphosphonic acid phosphonate inhibitor Salmonella enterica subsp. enterica serovar Typhimurium
4.2.1.20 4-(2-hydroxy-5-fluorophenylthio)butylphosphonic acid phosphonate inhibitor Salmonella enterica subsp. enterica serovar Typhimurium
4.2.1.20 4-(2-hydroxyphenylsulfinyl)butylphosphonic acid phosphonate inhibitor Salmonella enterica subsp. enterica serovar Typhimurium
4.2.1.20 4-(2-hydroxyphenylthio)-1-butenylphosphoric acid phosphonate inhibitor Salmonella enterica subsp. enterica serovar Typhimurium
4.2.1.20 4-(2-hydroxyphenylthio)butylphosphonic acid phosphonate inhibitor Salmonella enterica subsp. enterica serovar Typhimurium
4.2.1.20 phosphonate inhibitors mimic the transition state of the alpha-reaction with higher affinities than the natural substrate indole 3-glycerol phosphate, inhibitor binding changes the conformation of active site residues Glu49 and Phe212, stabilization of the enzyme inhibitor complex by short hydrogen bond between a phosphonate oxygen and Ser235 hydroxyl oxygen, inhibition mechanism Salmonella enterica subsp. enterica serovar Typhimurium

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
4.2.1.20 1-(indol-3-yl)glycerol 3-phosphate Salmonella enterica subsp. enterica serovar Typhimurium alpha-subunit of the bienzyme complex, alpha-reaction D-glyceraldehyde 3-phosphate + indole
-
 ?
4.2.1.20 L-serine + indole Salmonella enterica subsp. enterica serovar Typhimurium beta-subunit of the bienzyme complex, beta-reaction L-tryptophan + H2O
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
4.2.1.20 Salmonella enterica subsp. enterica serovar Typhimurium
-
-
-

Reaction

EC Number Reaction Comment Organism Reaction ID
4.2.1.20 L-serine + 1-C-(indol-3-yl)glycerol 3-phosphate = L-tryptophan + D-glyceraldehyde 3-phosphate + H2O also catalyses the conversion of serine and indole into tryptophan and water, and of indoleglycerol phosphate into indole and glyceraldehyde phosphate (the latter reaction was listed formerly as EC 4.2.1.8), detailed alpha-subunit catalytic mechanism Salmonella enterica subsp. enterica serovar Typhimurium
a

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
4.2.1.20 1-(indol-3-yl)glycerol 3-phosphate alpha-subunit of the bienzyme complex, alpha-reaction Salmonella enterica subsp. enterica serovar Typhimurium D-glyceraldehyde 3-phosphate + indole
-
 ?
4.2.1.20 L-serine + indole beta-subunit of the bienzyme complex, beta-reaction Salmonella enterica subsp. enterica serovar Typhimurium L-tryptophan + H2O
-
 ?

Synonyms

EC Number Synonyms Comment Organism
4.2.1.20 TRPS
-
 Salmonella enterica subsp. enterica serovar Typhimurium

Ki Value [mM]

EC Number Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
4.2.1.20 additional information
-
 additional information
-
 Salmonella enterica subsp. enterica serovar Typhimurium