Information on EC 1.14.16.4 - tryptophan 5-monooxygenase and Organism(s) Mus musculus and UniProt Accession P17532

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Mus musculus
UNIPROT: P17532


The expected taxonomic range for this enzyme is: Eukaryota, Bacteria


The taxonomic range for the selected organisms is: Mus musculus

EC NUMBER
COMMENTARY hide
1.14.16.4
-
RECOMMENDED NAME
GeneOntology No.
tryptophan 5-monooxygenase
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
-
-
-
-
redox reaction
-
-
-
-
reduction
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
serotonin and melatonin biosynthesis
-
-
Tryptophan metabolism
-
-
Folate biosynthesis
-
-
Metabolic pathways
-
-
SYSTEMATIC NAME
IUBMB Comments
L-tryptophan,tetrahydrobiopterin:oxygen oxidoreductase (5-hydroxylating)
The active centre contains mononuclear iron(II). The enzyme is activated by phosphorylation, catalysed by a Ca2+-activated protein kinase. The 4a-hydroxytetrahydrobiopterin formed can dehydrate to 6,7-dihydrobiopterin, both spontaneously and by the action of EC 4.2.1.96, 4a-hydroxytetrahydrobiopterin dehydratase. The 6,7-dihydrobiopterin can be enzymically reduced back to tetrahydrobiopterin, by EC 1.5.1.34 (6,7-dihydropteridine reductase), or slowly rearranges into the more stable compound 7,8-dihydrobiopterin.
CAS REGISTRY NUMBER
COMMENTARY hide
9037-21-2
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
TPH1; isozyme TPH1
UniProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
-
enzyme-deficient mice have elevated serum tryptophan levels, a normal mast cell compartment and enhanced signaling of mammalian target of rapamycin. Enzyme deficiency exacerbates experimental autoimmune encephalomyelitis
metabolism
-
rate-limiting enzyme in the serotonin biosynthesis
physiological function
-
the enzyme is a potent regulator of immunity regulating immune tolerance and inflammation. The enzyme is essential for the generation of protective T cell–mediated antitumor immunity
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
show the reaction diagram
L-phenylalanine + tetrahydropteridine + O2
tyrosine + dihydropteridine + H2O
show the reaction diagram
L-tryptophan + (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
show the reaction diagram
-
-
-
-
?
L-tryptophan + 6-methyl-tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 6-methyl-4a-hydroxytetrahydrobiopterin
show the reaction diagram
-
-
-
-
?
L-tryptophan + tetrahydrobiopterin
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
show the reaction diagram
-
-
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
show the reaction diagram
L-tryptophan + tetrahydropteridine + O2
5-hydroxy-L-tryptophan + dihydropteridine + H2O
show the reaction diagram
L-tyrosine + tetrahydropteridine + O2
?
show the reaction diagram
-
1% of activity with L-tryptophan
-
-
?
additional information
?
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
show the reaction diagram
P17532, Q8CGV2
TPH catalyzes the first step and rate-limiting reaction in the biosynthesis of 5-hydroxytryptamine, i.e. serotonin, and plays a role in brain and serotonergic neuron development, also TPH1 is involved in behavioural disorders, overview
-
-
?
L-tryptophan + (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
show the reaction diagram
-
-
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
show the reaction diagram
L-tryptophan + tetrahydropteridine + O2
5-hydroxy-L-tryptophan + dihydropteridine + H2O
show the reaction diagram
additional information
?
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
tetrahydrobiopterin
-
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1,10-phenanthroline
-
-
2,2'-dipyridyl
-
-
3,4-dihydroxyphenylalanine
-
-
3,4-Dihydroxyphenylethylamine
-
-
3-(4-amino-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)phenylalanine
-
-
3-amino-3-[4-(4-amino-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)phenyl]propanoic acid
-
-
3-[1-(4-amino-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)piperidin-4-yl]alanine
-
-
3-[3-(4-amino-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)-1H-pyrazol-1-yl]alanine
-
-
3-[5-(4-amino-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)pyridin-2-yl]alanine
-
-
4-(4-amino-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)-2-fluorophenylalanine
-
-
4-(4-amino-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)-a-methylphenylalanine
-
-
4-(4-amino-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)-L-phenylalanine
4-(5-[[(1-hydroxy-1,2,3,4-tetrahydronaphthalen-2-yl)methyl]amino]pyrazin-2-yl)-L-phenylalanine
-
-
4-(5-[[(1-hydroxynaphthalen-2-yl)methyl]amino]pyrazin-2-yl)-L-phenylalanine
-
-
4-(5-[[(2'-methylbiphenyl-2-yl)methyl]amino]pyrazin-2-yl)-L-phenylalanine
-
-
4-(5-[[(9-ethyl-9H-carbazol-3-yl)methyl]amino]pyrazin-2-yl)-L-phenylalanine
-
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4-(5-[[3-(cyclopentyloxy)-4-methoxybenzyl]amino]pyrazin-2-yl)-L-phenylalanine
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-
4-chloro-L-phenylalanine
-
irreversible inhibitor
4-Chlorophenylalanine
4-ethynylphenylalanine
-
-
4-Fluorotryptophan
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4-[4-amino-6-(1-naphthalen-2-ylethoxy)-1,3,5-triazin-2-yl]-L-phenylalanine
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-
4-[4-amino-6-(2,2,2-trifluoro-1-naphthalen-2-ylethoxy)-1,3,5-triazin-2-yl]-L-phenylalanine
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-
4-[4-amino-6-(2,2,2-trifluoro-1-[2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]phenyl]ethoxy)-1,3,5-triazin-2-yl]-L-phenylalanine
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4-[4-amino-6-[2,2,2-trifluoro-1-(2-furan-2-ylphenyl)ethoxy]-1,3,5-triazin-2-yl]-L-phenylalanine
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4-[4-amino-6-[2,2,2-trifluoro-1-(3'-methylbiphenyl-2-yl)ethoxy]-1,3,5-triazin-2-yl]-L-phenylalanine
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4-[4-amino-6-[2,2,2-trifluoro-1-(5-furan-2-ylthiophen-2-yl)ethoxy]-1,3,5-triazin-2-yl]-L-phenylalanine
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4-[5-[(3,4-dimethoxybenzyl)amino]pyrazin-2-yl]-L-phenylalanine
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4-[5-[(4-cyanobenzyl)amino]pyrazin-2-yl]-L-phenylalanine
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4-[5-[(biphenyl-4-ylmethyl)amino]pyrazin-2-yl]-L-phenylalanine
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4-[5-[(cyclohexylmethyl)amino]pyrazin-2-yl]-L-phenylalanine
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4-[5-[(furan-3-ylmethyl)amino]pyrazin-2-yl]-L-phenylalanine
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4-[5-[(pyridin-3-ylmethyl)amino]pyrazin-2-yl]-L-phenylalanine
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4-[5-[(quinolin-3-ylmethyl)amino]pyrazin-2-yl]-L-phenylalanine
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5-Fluorotryptophan
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5-hydroxytryptophan
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6-Fluorotryptophan
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8-hydroxyquinoline
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D-Dopa
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noncompetitive vs. L-tryptophan and (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin
dopamine
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noncompetitive vs. L-tryptophan and (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin
L-4-chlorophenylalanine
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L-Dopa
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noncompetitive vs. L-tryptophan and (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin
L-p-Chlorophenylalanine
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L-phenylalanine
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competitive vs. tryptophan
L-tryptophan
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competitive to L-phenylalanine
L-tyrosine
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noncompetitive vs. L-tryptophan and (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin
LP-533401
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LP-615819
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serotonin
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1 mM, 7.5% inhibition, 10 mM, 70% inhibition
additional information
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2-mercaptoethanol
2-mercaptoethylamine
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30 mM, 93.8% activity compared to activation with dithiothreitol
2-mercaptopropionate
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30 mM, 11.7% activity compared to activation with dithiothreitol
3-Mercaptopropionate
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30 mM, 22% activity compared to activation with dithiothreitol
dithiothreitol
Fe(NH4)2(SO4)2
-
-
glutathione
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30 mM, 16.1% activity compared to activation with dithiothreitol
L-cysteine
N-acetylcysteine
-
30 mM, 31.2% activity compared to activation with dithiothreitol
additional information
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0075 - 0.0166
L-tryptophan
0.0344 - 0.796
(6R)-L-erythro-5,6,7,8-tetrahydrobiopterin
0.055 - 0.0752
2-amino-4-hydroxy-6-methyltetrahydropteridine
0.1
L-phenylalanine
-
cofactor 2-amino-4-hydroxy-6-methyltetrahydropteridine
0.0075 - 0.355
L-tryptophan
0.294
tetrahydrobiopterin
-
activated enzyme in desalted extracts
additional information
additional information
-
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0761 - 0.609
D-Dopa
0.007 - 0.0943
dopamine
0.026
L-4-chlorophenylalanine
-
-
0.017 - 0.0887
L-Dopa
0.0162 - 0.306
L-tyrosine
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.011
3-(4-amino-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)phenylalanine
Mus musculus;
-
-
0.00377
3-amino-3-[4-(4-amino-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)phenyl]propanoic acid
Mus musculus;
-
-
0.00077
3-[1-(4-amino-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)piperidin-4-yl]alanine
Mus musculus;
-
-
0.0126
3-[3-(4-amino-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)-1H-pyrazol-1-yl]alanine
Mus musculus;
-
-
0.00089
3-[5-(4-amino-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)pyridin-2-yl]alanine
Mus musculus;
-
-
0.0002
4-(4-amino-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)-2-fluorophenylalanine
Mus musculus;
-
-
0.0111
4-(4-amino-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)-a-methylphenylalanine
Mus musculus;
-
-
0.000026 - 0.000032
4-(4-amino-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)-L-phenylalanine
0.000046
4-(5-[[(1-hydroxy-1,2,3,4-tetrahydronaphthalen-2-yl)methyl]amino]pyrazin-2-yl)-L-phenylalanine
Mus musculus;
-
-
0.000013
4-(5-[[(1-hydroxynaphthalen-2-yl)methyl]amino]pyrazin-2-yl)-L-phenylalanine
Mus musculus;
-
-
0.00004
4-(5-[[(2'-methylbiphenyl-2-yl)methyl]amino]pyrazin-2-yl)-L-phenylalanine
Mus musculus;
-
-
0.000031
4-(5-[[(9-ethyl-9H-carbazol-3-yl)methyl]amino]pyrazin-2-yl)-L-phenylalanine
Mus musculus;
-
-
0.000045
4-(5-[[3-(cyclopentyloxy)-4-methoxybenzyl]amino]pyrazin-2-yl)-L-phenylalanine
Mus musculus;
-
-
0.092
4-Chlorophenylalanine
Mus musculus;
-
-
0.03
4-ethynylphenylalanine
Mus musculus;
-
-
0.00038
4-[4-amino-6-(1-naphthalen-2-ylethoxy)-1,3,5-triazin-2-yl]-L-phenylalanine
Mus musculus;
-
-
0.00018
4-[4-amino-6-(2,2,2-trifluoro-1-naphthalen-2-ylethoxy)-1,3,5-triazin-2-yl]-L-phenylalanine
Mus musculus;
-
-
0.000029
4-[4-amino-6-(2,2,2-trifluoro-1-[2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]phenyl]ethoxy)-1,3,5-triazin-2-yl]-L-phenylalanine
Mus musculus;
-
-
0.000024
4-[4-amino-6-[2,2,2-trifluoro-1-(2-furan-2-ylphenyl)ethoxy]-1,3,5-triazin-2-yl]-L-phenylalanine
Mus musculus;
-
-
0.00007
4-[4-amino-6-[2,2,2-trifluoro-1-(3'-methylbiphenyl-2-yl)ethoxy]-1,3,5-triazin-2-yl]-L-phenylalanine
Mus musculus;
-
-
0.000054
4-[4-amino-6-[2,2,2-trifluoro-1-(5-furan-2-ylthiophen-2-yl)ethoxy]-1,3,5-triazin-2-yl]-L-phenylalanine
Mus musculus;
-
-
0.000069
4-[5-[(3,4-dimethoxybenzyl)amino]pyrazin-2-yl]-L-phenylalanine
Mus musculus;
-
-
0.00011
4-[5-[(4-cyanobenzyl)amino]pyrazin-2-yl]-L-phenylalanine
Mus musculus;
-
-
0.000044
4-[5-[(biphenyl-4-ylmethyl)amino]pyrazin-2-yl]-L-phenylalanine
Mus musculus;
-
-
0.00024
4-[5-[(cyclohexylmethyl)amino]pyrazin-2-yl]-L-phenylalanine
Mus musculus;
-
-
0.00096
4-[5-[(furan-3-ylmethyl)amino]pyrazin-2-yl]-L-phenylalanine
Mus musculus;
-
-
0.00615
4-[5-[(pyridin-3-ylmethyl)amino]pyrazin-2-yl]-L-phenylalanine
Mus musculus;
-
-
0.00019
4-[5-[(quinolin-3-ylmethyl)amino]pyrazin-2-yl]-L-phenylalanine
Mus musculus;
-
-
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.434
-
recombinant enzyme, activity in cell extracts
additional information
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.5
-
assay at
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6 - 8.7
-
about 50% activity at pH 6.0 and 8.7
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
30
-
assay at
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
temporal expression pattern of TPH1
Manually annotated by BRENDA team
-
-
Manually annotated by BRENDA team
-
-
Manually annotated by BRENDA team
-
-
Manually annotated by BRENDA team
additional information
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
47000
-
x * 47000, recombinant enzyme, SDS-PAGE
53000
-
4 * 53000, enzyme from mastocytoma cells, SDS-PAGE
56000
-
4 * 56000, SDS-PAGE
270000
-
enzyme from mastocytoma cells, gel filtration
280000
-
enzyme from mastocytoma cells, gradient PAGE
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
-
x * 47000, recombinant enzyme, SDS-PAGE
homotetramer
-
4 * 56000, SDS-PAGE
tetramer
-
4 * 53000, enzyme from mastocytoma cells, SDS-PAGE
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
phosphoprotein
-
tryptophan hydroxylase becomes phosphorylated at Ser58 in brain stem of 1-month-old SAMP6
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
4
-
complete loss of activity in absence of stabilizing agents after 20 h
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
catalase at a concentration of more than 1 mg/ml is required for stability during reaction at aerobic conditiones
-
EDTA stabilizes
-
EDTA: 0.05 mM stabilizes
-
ethylene glycol, 50%, stabilizes
-
NaCl: 1 M, in addition to other stabilizing agents brings a great improvement in stabilization
-
Tween 20 stabilizes
-
Tween 20: 0.06% stabilizes
-
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-20°C, 10% glycerol, 0.05 mM EDTA, 0.06% Tween 20, 28 d, 69% loss of activity
-
-80°C, 1 month, 30% loss of activity
-
4°C, 0.06% Tween 20, 0.05 mM EDTA, 50% ethylene glycol, 1 M NaCl, 5 days, no loss of activity
-
4°C, 10% glycerol, 0.05 mM EDTA, 0.06% Tween 20, 28 d, 34% loss of activity
-
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
2-amino-4-hydroxy-6,7-dimethyltetrahydropteridine-agarose
-
one chromatography step, 98% homogeneity
-
purified and cleaved from its fusion tag
-
recombinant isozymes TPH1 and TPH2 from Escherichia coli by pterin affinity chromatography
-
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
isozyme TPH1, DNA and amino acid sequence determination and analysis, tissue-specific and developmental expression analysis, expression of His6-tagged TPH1 in COS7 cells
expression in Escherichia coli
-
expression of isozymes TPH1 and TPH2 in Escherichia coli
-
expression of TPH2 in COS cells
-
genes Tph1 and Tph2, expression analysis in wild-type and mutant mice, overview
-
glutathione S-transferase-fusion protein expressed in Escherichia coli, expressed in HEK293-cell, eGFP-fusion protein expressed in HEK293-cell
-
into pT vector and linearized with Nco I prior to antisense transcription with SP6
-
isozyme TPH2, DNA and amino acid sequence determination and analysis, tissue-specific and developmental expression analysis, expression of His6-tagged TPH2 in COS7 cells
secondary structure of TPH1 RNA, overview
-
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
enzyme expression is induced by prolactin
-
enzyme expression is inhibited by a Jak2 inhibitor and partially inhibited by MEK1/2 inhibitor U0126 or PI3K inhibitor LY-294002
-
imipramine increases dorsal raphe TPH2 gene expression in a glucocorticoid-dependent manner, increases are due to relief of inhibitory glucocorticoid signaling
-
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
C110S/C112S
-
all cysteine residues of the regulatory domain mutated
C110S/C112S/C162S/C234S/C248S/C296S
-
six N-terminal-most cysteines mutated
C110S/C112S/C162S/C234S/C248S/C296S/C315S/C355S/C365S/C394S/C404S/C408S/C476S
-
all 13 cysteine residues mutated
C110S/C162S/C234S/C248S/C296S/C355S/C365S/C394S/C404S/C408S/C476S
-
mutant protein containing a single cysteine residue within the regulatory domain (Cys112) and within the catalytic core domain (Cys315)
C1473G
-
naturally occuring polymorphism of gene Tph2, C57Bl/6 and 129X1/SvJ mice are homozygous for the 1473C allele, whereas DBA/2 and BALB/cJ mice are homozygous for the 1473G allele, comparison of pulmonary hypertension and vascular remodeling of haplotypes, overview
C162S/C234S/C248S/C296S/C315S/C355S/C365S/C394S/C404S/C408S/C476S
-
all cysteine residues of the catalytic core domain mutated
C315S/C355S/C365S/C394S/C404S/C408S/C476S
-
seven C-terminal-most cysteines mutated
C476S
-
residue of the tetramerization domain
DELTA-C-terminal 24 residues
-
removed tetramerization domain
DELTA1-40
-
simulates tyrosine hydroxylase 1
G1473C
-
naturally occuring polymorphism, citalopram raises basal extracellular serotonin levels in DBA/2J, DBA/2N and BALB/c mice carrying the 1473G allele, but not in C57BL/6J and C57BL/6N mice carrying the 1473C allele, overview
P447R
the C1473G naturally occuring polymorphism in gene tph2 is the main factor mediating the genetically defined variability of tryptophan hydroxylase-2 activity in the mouse brain, phenotypes, overview
additional information
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
drug development
-
substituted 3-(4-(1,3,5-triazin-2-yl)-phenyl)-2-aminopropanoic acids as novel TPH1 inhibitors may provide novel treatments for gastrointestinal disorders associated with dysregulation of the serotonergic system, such as chemotherapy-induced emesis and irritable bowel syndrome