Literature summary for 1.13.11.52 extracted from

Southan, M.D.; Truscott, R.J.W.; Jamie, J.F.; Pelosi, L.; Walker, M.J.; Maeda, H.; Iwamoto, Y.; Tone, S.
Structural requirements of the competitive binding site of recombinant human indoleamine 2,3-dioxygenase (1996), Med. Chem. Res., 6, 343-352.

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Application

Application	Comment	Organism
pharmacology	first reaction in the tryptophan catabolic pathway in mammals	Homo sapiens

Cloned(Commentary)

Cloned (Comment)	Organism
expression in Escherichia coli strain YA21	Homo sapiens

Inhibitors

Inhibitors	Comment	Organism
1-benzofuran-DL-tryptophan	1 mM, 43% inhibition relative to L-tryptophan, 50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min	Homo sapiens
1-benzothiophene-DL-tryptophan	1 mM, 16% inhibition relative to L-tryptophan, 50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min	Homo sapiens
1-methyl-DL-tryptophan	1 mM, 26% inhibition relative to L-tryptophan, 50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min	Homo sapiens
2-bromo-L-tryptophan	1 mM, 11% inhibition relative to L-tryptophan, 50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min	Homo sapiens
2-chloro-L-tryptophan	1 mM, 20% inhibition relative to L-tryptophan, 50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min	Homo sapiens
2-hydroxy-L-tryptophan	1 mM, 30% inhibition relative to L-tryptophan, 50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min	Homo sapiens
4-methyl-DL-tryptophan	1 mM, 26% inhibition relative to L-tryptophan, 50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min	Homo sapiens
5-benzyloxy-DL-tryptophan	1 mM, 2% inhibition relative to L-tryptophan, 50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min	Homo sapiens
5-bromo-DL-tryptophan	1 mM, 56% inhibition relative to L-tryptophan, 50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min	Homo sapiens
5-fluoro-DL-tryptophan	1 mM, 32% inhibition relative to L-tryptophan, 50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min	Homo sapiens
5-hydroxy-L-tryptophan	1 mM, 12% inhibition relative to L-tryptophan, 50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min	Homo sapiens
5-methoxy-DL-tryptophan	1 mM, 35% inhibition relative to L-tryptophan, 50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min	Homo sapiens
5-methyl-DL-tryptophan	1 mM, 6% inhibition relative to L-tryptophan, 50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min	Homo sapiens
6-fluoro-DL-tryptophan	1 mM, 54% inhibition relative to L-tryptophan, 50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min	Homo sapiens
6-methyl-DL-tryptophan	1 mM, 20% inhibition relative to L-tryptophan, 50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min	Homo sapiens
6-nitro-D-tryptophan	1 mM, 7% inhibition relative to L-tryptophan, 50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min	Homo sapiens
6-nitro-L-tryptophan	1 mM, competitive inhibition, 52% inhibition relative to L-tryptophan, 50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min	Homo sapiens
7-methyl-DL-tryptophan	1 mM, 36% inhibition relative to L-tryptophan, 50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min	Homo sapiens
alpha-methyl-DL-tryptophan	1 mM, 1% inhibition relative to L-tryptophan, 50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min	Homo sapiens
alpha-N-methyl-L-tryptophan	1 mM, 33% inhibition relative to L-tryptophan, 50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min	Homo sapiens
beta-Methyl-DL-tryptophan	1 mM, 7% inhibition relative to L-tryptophan, 50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min	Homo sapiens
Indole-3-propionic acid	-	Homo sapiens
L-tryptophan	substrate inhibition at 0.14 mM and greater	Homo sapiens
L-tryptophan ethyl ester	1 mM, 7% inhibition relative to L-tryptophan, 50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min	Homo sapiens
L-tryptophan methyl ester	1 mM, 30% inhibition relative to L-tryptophan, 50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min	Homo sapiens
additional information	not inhibited by 6-nitro-D-tryptophan and indole-nitrogen substituted analogues of trytophan	Homo sapiens
N-acetyl-L-tryptophan	1 mM, 7% inhibition relative to L-tryptophan, 50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min	Homo sapiens
tryptamine	-	Homo sapiens

KM Value [mM]

KM Value [mM]	KM Value Maximum [mM]	Substrate	Comment	Organism
0.018	-	L-tryptophan	50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min	Homo sapiens
0.056	-	6-methyl-DL-tryptophan	50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min	Homo sapiens
0.088	-	5-methyl-DL-tryptophan	50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min	Homo sapiens
0.113	-	5-methoxy-DL-tryptophan	50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min	Homo sapiens
3.795	-	D-tryptophan	50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min	Homo sapiens

Natural Substrates/ Products (Substrates)

Natural Substrates	Organism	Comment (Nat. Sub.)	Natural Products	Comment (Nat. Pro.)	Rev.	Reac.
D-tryptophan + O2	Homo sapiens	-	N-formyl-D-kynurenine	-	?
L-tryptophan + O2	Homo sapiens	-	N-formyl-L-kynurenine	-	?

Organism

Organism	UniProt	Comment	Textmining
Homo sapiens	-	-	-

Purification (Commentary)

Purification (Comment)	Organism
-	Homo sapiens

Storage Stability

Storage Stability	Organism
-20°C, losing 70% activity after 24 h, addition of 5 mg/ml bovine serum albumin maintains 80% activity after 5 days	Homo sapiens

Substrates and Products (Substrate)

Substrates	Comment Substrates	Organism	Products	Comment (Products)	Rev.
1-benzofuran-DL-tryptophan + O2	1 mM, 22% activity relative to L-tryptophan, 50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min	Homo sapiens	?	-	?
1-benzothiophene-DL-tryptophan + O2	1 mM, 19% activity relative to L-tryptophan, 50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min	Homo sapiens	?	-	?
1-methyl-DL-tryptophan + O2	1 mM, 7% activity relative to L-tryptophan, 50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min	Homo sapiens	?	-	?
2-bromo-L-tryptophan + O2	1 mM, 21% activity relative to L-tryptophan, 50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min	Homo sapiens	?	-	?
2-chloro-L-tryptophan + O2	1 mM, 33% activity relative to L-tryptophan, 50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min	Homo sapiens	?	-	?
2-hydroxy-L-tryptophan + O2	1 mM, 4% activity relative to L-tryptophan, 50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min	Homo sapiens	?	-	?
4-methyl-DL-tryptophan + O2	1 mM, 33% activity relative to L-tryptophan, 50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min	Homo sapiens	?	-	?
5-benzyloxy-DL-tryptophan + O2	1 mM, 1% activity relative to L-tryptophan, 50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min	Homo sapiens	?	-	?
5-bromo-DL-tryptophan + O2	1 mM, 36% activity relative to L-tryptophan, 50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min	Homo sapiens	?	-	?
5-fluoro-DL-tryptophan + O2	1 mM, 46% activity relative to L-tryptophan, 50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min	Homo sapiens	?	-	?
5-hydroxy-L-tryptophan + O2	1 mM, 59% activity relative to L-tryptophan, 50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min	Homo sapiens	?	-	?
5-methoxy-D,L-tryptophan + O2	1 mM, 70% activity relative to L-tryptophan, 50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min	Homo sapiens	?	-	?
5-methyl-D,L-tryptophan + O2	1 mM, 123% activity relative to L-tryptophan, 50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min	Homo sapiens	?	-	?
6-fluoro-DL-tryptophan + O2	1 mM, 38% activity relative to L-tryptophan, 50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min	Homo sapiens	?	-	?
6-methyl-DL-tryptophan + O2	1 mM, 72% activity relative to L-tryptophan, 50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min	Homo sapiens	?	-	?
6-nitro-L-tryptophan + O2	1 mM, 2% activity relative to L-tryptophan, 50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min	Homo sapiens	?	-	?
7-methyl-DL-tryptophan + O2	1 mM, 18% activity relative to L-tryptophan, 50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min	Homo sapiens	?	-	?
alpha-methyl-DL-tryptophan + O2	1 mM, 35% activity relative to L-tryptophan, 50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min	Homo sapiens	?	-	?
alpha-N-methyl-L-tryptophan + O2	1 mM, 21% activity relative to L-tryptophan, 50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min	Homo sapiens	?	-	?
beta-methyl-DL-tryptophan + O2	1 mM, 32% activity relative to L-tryptophan, 50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min	Homo sapiens	?	-	?
D-tryptophan + O2	-	Homo sapiens	N-formyl-D-kynurenine	-	?
L-tryptophan + O2	-	Homo sapiens	N-formyl-L-kynurenine	-	?
L-tryptophan ethyl ester + O2	1 mM, 14% activity relative to L-tryptophan, 50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min	Homo sapiens	?	-	?
L-tryptophan methyl ester + O2	1 mM, 15% activity relative to L-tryptophan, 50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min	Homo sapiens	?	-	?
N-acetyl-L-tryptophan + O2	1 mM, 3% activity relative to L-tryptophan, 50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min	Homo sapiens	?	-	?

Synonyms

Synonyms	Comment	Organism
IDO	-	Homo sapiens

Temperature Stability [°C]

Temperature Stability Minimum [°C]	Temperature Stability Maximum [°C]	Comment	Organism
-20	-	losing 70% activity after 24 h, addition of 5 mg/ml BSA maintaines 80% activity after 5 days	Homo sapiens
4	-	maintaines 70% activity with addition of 2 mg/ml catalase for 4 days	Homo sapiens

pH Optimum

pH Optimum Minimum	pH Optimum Maximum	Comment	Organism
6.6	6.8	in 50 mM phosphate buffer	Homo sapiens

Ki Value [mM]

Ki Value [mM]	Ki Value maximum [mM]	Inhibitor	Comment	Organism	Structure
0.18	-	6-nitro-L-tryptophan	1 mM, competitive inhibition, 52% inhibition relative to L-tryptophan, 50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min	Homo sapiens