L-Tyrosine (YMDB00364)

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Identification

YMDB ID

YMDB00364

Name

L-Tyrosine

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

Tyrosine (abbreviated as Tyr or Y) is an alpha-amino acid. The L-isomer is one of the 22 proteinogenic amino acids, i.e., the building blocks of proteins. It is classified as a nonpolar, aromatic amino acid, because of the hydrophobic nature of the phenol side chain. L-Tyrosine is an electrically neutral amino acid. The word 'tyrosine' is from the Greek tyri, meaning cheese, as it was first discovered in 1846 by German chemist Justus von Liebig in the protein casein from cheese. Aside from being a proteogenic amino acid, tyrosine has a special role by virtue of the phenol functionality. It occurs in proteins that are part of signal transduction processes. It functions as a receiver of phosphate groups that are transferred by way of protein kinases (so-called receptor tyrosine kinases). Phosphorylation of the hydroxyl group changes the activity of the target protein. Tyrosine is produced via prephenate, an intermediate on the shikimate pathway. Prephenate is oxidatively decarboxylated with retention of the hydroxyl group to give p-hydroxyphenylpyruvate, which is transaminated using glutamate as the nitrogen source to give tyrosine and alpha-ketoglutarate. In yeast, the biosynthesis of phenylalanine, tyrosine, and tryptophan proceeds via a common pathway to chorismate, at which point the pathway branches. One branch proceeds to phenylalanine and tyrosine, and the other to tryptophan. The phenylalanine and tyrosine branch has one reaction in common, rearrangement of chorismate to prephenate, at which point, the pathway branches again to either phenylalanine or tyrosine. S. cerevisiae, similar to E. coli, synthesizes phenylalanine and tyrosine via the intermediate 4-hydroxyphenylpyruvate and phenylpyruvate, respectively. Aromatic amino acid biosynthesis in S. cerevisiae is controlled by a combination of feedback inhibition, activation of enzyme activity, and regulation of enzyme synthesis. The carbon flow through the pathways is regulated primarily at the initial step and the branching points by the terminal end-products. The initial step of chorismate biosynthesis can be catalyzed by two isoenzymes Aro3p or Aro4p, whereby Aro3p is inhibited by phenylalanine, and Aro4p by tyrosine. The first step in the phenylalanine-tyrosine branch is feedback inhibited by tyrosine and activated by tryptophan. S. cerevisiae degrade the aromatic amino acids (tryptophan, phenylalanine, and tyrosine) via the Ehrlich pathway. This pathway consists of 3 steps: 1) deamination of the amino acid to the corresponding alpha-keto acid; 2) decarboxylation of the resulting alpha-keto acid to the respective aldehyde; and, 3) reduction of the aldehyde to form the corresponding long chain or complex alcohol, known as a fusel alcohol or fusel oil. Fusel alcohols are important flavor and aroma compounds in yeast-fermented food products and beverages. Aro10p appears to be the primary decarboxylase catalyzing the second step in phenylalanine degradation. Although Vulrahan et. al. (2003) found that THI3 does not encode an active phenylpyruvate decarboxylase, they found Thi3p was required in conjunction with one of the pyruvate decarboxylases Pdc1p, Pdc5p or Pdc6p for the ARO10-independent decarboxylase activity. The main uptake systems for utilizing aromatic amino acids appear to be Gap1p, a general amino acid permease, and Wap1p, an inducible amino acid permease with wide substrate specificity.

Structure

MOL SDF PDB SMILES InChI

Synonyms

(-)-a-Amino-p-hydroxyhydrocinnamate
(-)-a-Amino-p-hydroxyhydrocinnamic acid
(-)-alpha-Amino-p-hydroxyhydrocinnamate
(-)-alpha-Amino-p-hydroxyhydrocinnamic acid
(S)-(-)-Tyrosine
(S)-2-Amino-3-(p-hydroxyphenyl)propionate
(S)-2-Amino-3-(p-hydroxyphenyl)propionic acid
(S)-3-(p-Hydroxyphenyl)alanine
(S)-a-amino-4-hydroxy-Benzenepropanoate
(S)-a-amino-4-hydroxy-Benzenepropanoic acid
(S)-a-Amino-4-hydroxybenzenepropanoate
(S)-a-Amino-4-hydroxybenzenepropanoic acid
(S)-alpha-amino-4-hydroxy-Benzenepropanoate
(S)-alpha-amino-4-hydroxy-Benzenepropanoic acid
(S)-alpha-Amino-4-hydroxybenzenepropanoate
(S)-alpha-Amino-4-hydroxybenzenepropanoic acid
(S)-Tyrosine
2-amino-3-(4-hydroxyphen yl)-2-amino-3-(4-hydroxyphenyl)-Propanoate
2-amino-3-(4-hydroxyphen yl)-2-amino-3-(4-hydroxyphenyl)-Propanoic acid
3-(4-Hydroxyphenyl)-L-alanine
4-hydroxy-L-Phenylalanine
Benzenepropanoate
Benzenepropanoic acid
L-p-Tyrosine
L-tyrosine
p-Tyrosine
Tyr
Tyrosine
(2S)-2-Amino-3-(4-hydroxyphenyl)propanoic acid
L-Tyrosin
Y
(-)-Α-amino-p-hydroxyhydrocinnamate
(-)-Α-amino-p-hydroxyhydrocinnamic acid
(2S)-2-Amino-3-(4-hydroxyphenyl)propanoate
(S)-Α-amino-4-hydroxybenzenepropanoate
(S)-Α-amino-4-hydroxybenzenepropanoic acid
L Tyrosine
Tyrosine, L-isomer
Tyrosine, L isomer
Para tyrosine
Para-tyrosine

CAS number

60-18-4

Weight

Average: 181.1885
Monoisotopic: 181.073893223

InChI Key

OUYCCCASQSFEME-QMMMGPOBSA-N

InChI

InChI=1S/C9H11NO3/c10-8(9(12)13)5-6-1-3-7(11)4-2-6/h1-4,8,11H,5,10H2,(H,12,13)/t8-/m0/s1

IUPAC Name

(2S)-2-amino-3-(4-hydroxyphenyl)propanoic acid

Traditional IUPAC Name

L-tyrosine

Chemical Formula

C₉H₁₁NO₃

SMILES

[H]OC(=O)[C@@]([H])(N([H])[H])C([H])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H]

Chemical Taxonomy

Description

belongs to the class of organic compounds known as tyrosine and derivatives. Tyrosine and derivatives are compounds containing tyrosine or a derivative thereof resulting from reaction of tyrosine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Tyrosine and derivatives

Alternative Parents

Substituents

Tyrosine or derivatives
Phenylalanine or derivatives
3-phenylpropanoic-acid
Alpha-amino acid
Amphetamine or derivatives
L-alpha-amino acid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Aralkylamine
Monocyclic benzene moiety
Benzenoid
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Organooxygen compound
Organonitrogen compound
Amine
Primary aliphatic amine
Organic nitrogen compound
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Hydrocarbon derivative
Primary amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

proteinogenic amino acid (CHEBI:17895 )
L-alpha-amino acid (CHEBI:17895 )
tyrosine (CHEBI:17895 )
erythrose 4-phosphate/phosphoenolpyruvate family amino acid (CHEBI:17895 )
Common amino acids (C00082 )

Physical Properties

State

Solid

Charge

Melting point

343 °C

Experimental Properties

Property	Value	Reference
Water Solubility	0.479 mg/mL at 25 oC [SEIDELL,A (1941)]	PhysProp
LogP	-2.26 [HANSCH,C ET AL. (1995)]	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	7.67 g/L	ALOGPS
logP	-2.4	ALOGPS
logP	-1.5	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	2	ChemAxon
pKa (Strongest Basic)	9.19	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	83.55 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	47.1 m³·mol⁻¹	ChemAxon
Polarizability	18.01 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

extracellular
mitochondrion
peroxisome
vacuole
cytoplasm

Organoleptic Properties

Flavour/Odour	Source
Odorless	FDB000446

SMPDB Pathways

Phenylalanine metabolism	PW002437
Tyrosine metabolism	PW002441

KEGG Pathways

Cyanoamino acid metabolism	ec00460
Phenylalanine metabolism	ec00360
Phenylalanine, tyrosine and tryptophan biosynthesis	ec00400
Thiamine metabolism	ec00730
Tyrosine metabolism	ec00350

SMPDB Reactions

(4-hydroxyphenyl)pyruvic acid + L-Alanine ↔ Pyruvic acid + L-Tyrosine

(4-hydroxyphenyl)pyruvic acid + L-Glutamic acid → Oxoglutaric acid + L-Tyrosine

KEGG Reactions

L-Tyrosine + N10-Formyl-THF → N-Formyl-L-tyrosine + 5,6,7,8-Tetrahydrofolic acid + hydron

L-Glutamic acid + (4-hydroxyphenyl)pyruvic acid → L-Tyrosine + Oxoglutaric acid

L-Tyrosine + Adenosine triphosphate + tRNA(Tyr) → Adenosine monophosphate + Pyrophosphate + Tyr-tRNA(Tyr)

Concentrations

Intracellular Concentrations

Intracellular Concentration	Substrate	Growth Conditions	Strain	Citation
283 ± 6 µM	YPD media	aerobic	Baker's yeast	PMID: 7654310
170 ± 3 µM	YPG media	aerobic	Baker's yeast	PMID: 7654310
340 ± 7 µM	SD media	aerobic	Baker's yeast	PMID: 7654310
453 ± 9 µM	SG media	aerobic	Baker's yeast	PMID: 7654310
1019 ± 21 µM	M (molasses)	aerobic	Baker's yeast	PMID: 7654310
4019 ± 80 µM	MA (molasses)	aerobic	Baker's yeast	PMID: 7654310
283 ± 6 µM	MB (molasses)	aerobic	Baker's yeast	PMID: 7654310
2604 ± 52 µM	MAB (molasses)	aerobic	Baker's yeast	PMID: 7654310
883 ± 44 µM	YEB media with 0.5 mM glucose	aerobic	Baker's yeast	Experimentally Determined Not Available
250 ± 33 µM	Synthetic medium with 20 g/L glucose	aerobic	Baker's yeast	PMID: 12584756
Conversion Details Here

Extracellular Concentrations

Intracellular Concentration	Substrate	Growth Conditions	Strain	Citation
1297 ± 143 µM	hops, malted barley	anaerobic	Baker's yeast	PMID: 16448171
Conversion Details Here

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)	splash10-014i-0690000000-cbbf40bb26fc84f2aead	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)	splash10-014i-0890000000-ca45f993f95c8b0cee44	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)	splash10-014i-0890000000-5749069211ba15d713ef	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)	splash10-00xr-9240000000-2c87373c0d964e0edef5	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-014i-0890000000-848b2a4f247a0b3f14e8	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)	splash10-00xr-9450000000-6d4550940f4dde6f18ff	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-004i-1910000000-5cc19cad5dc24b3b9b11	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-014i-1790000000-de22041357aadf60a06b	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014i-0690000000-cbbf40bb26fc84f2aead	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014i-0890000000-ca45f993f95c8b0cee44	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014i-0890000000-5749069211ba15d713ef	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00xr-9240000000-2c87373c0d964e0edef5	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014i-0890000000-848b2a4f247a0b3f14e8	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-QQ (Non-derivatized)	splash10-0udi-3319000000-1d3d28a67f82366fff22	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00xr-9450000000-6d4550940f4dde6f18ff	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-004i-1910000000-5cc19cad5dc24b3b9b11	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-014i-1790000000-de22041357aadf60a06b	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-052r-4900000000-9be1412408207db5df4e	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-05fr-9750000000-937b6ee7a745865ee7ee	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-01p9-0900000000-580de2c16cd24559cd5c	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0006-9400000000-f233fbc6c58236ee4aeb	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-002f-9100000000-8b5e12eba034bcfdf8a1	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0920000000-b43356ad3da227b488cb	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-014i-0900000000-c04f0be6515621dda5ac	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-0900000000-3ed8b68bfade9194763b	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0udi-0900000000-fe6a1ce69851a8c5db00	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0900000000-aafdcea07be221817fd4	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0002-0900000000-66a5b9a0a48bdc0a2b47	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-014i-0900000000-13eb4252ca23455a58da	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-014i-0900000000-fb85798746829bac3f3d	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-03e9-0839226000-5504e667281c746669ec	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-03di-0900000000-f65cb3ad2fa730c922f7	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-001i-0900000000-a9276fe43ef61b4693e6	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0a59-0039210000-21b4bd9870bf4965a6d1	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-001i-0848491200-aae99eb0b66dd1c7036d	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-03di-0900000000-4104a2ca5d5ef5f22f6d	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-001i-0900000000-f309996d57a95c719deb	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-03di-0013090000-112cd9c2eea42dbc079b	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-001i-0900000000-c7f95918d936586f633d	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-03yi-1900000000-d1682546c1e0893c71e4	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-014i-2900000000-a0cc78ed35e56dd812a5	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-00kf-9500000000-d3f399f5dd10e338e25a	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0006-9200000000-8acd8d370f194bfe28ed	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-001i-0900000000-6b26ce2f5b326ace12a4	JSpectraViewer \| MoNA
MS	Mass Spectrum (Electron Ionization)	splash10-0a4i-3900000000-7a26097fda66f2f445b5	JSpectraViewer \| MoNA
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	JSpectraViewer

References

References:

Martinez-Force, E., Benitez, T. (1995). "Effects of varying media, temperature, and growth rates on the intracellular concentrations of yeast amino acids." Biotechnol Prog 11:386-392.7654310
UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
Vaseghi, S., Baumeister, A., Rizzi, M., Reuss, M. (1999). "In vivo dynamics of the pentose phosphate pathway in Saccharomyces cerevisiae." Metab Eng 1:128-140.10935926
Almeida, C., Duarte, I. F., Barros, A., Rodrigues, J., Spraul, M., Gil, A. M. (2006). "Composition of beer by 1H NMR spectroscopy: effects of brewing site and date of production." J Agric Food Chem 54:700-706.16448171
Hans, M. A., Heinzle, E., Wittmann, C. (2003). "Free intracellular amino acid pools during autonomous oscillations in Saccharomyces cerevisiae." Biotechnol Bioeng 82:143-151.12584756
Nookaew, I., Jewett, M. C., Meechai, A., Thammarongtham, C., Laoteng, K., Cheevadhanarak, S., Nielsen, J., Bhumiratana, S. (2008). "The genome-scale metabolic model iIN800 of Saccharomyces cerevisiae and its validation: a scaffold to query lipid metabolism." BMC Syst Biol 2:71.18687109
Yang, Z., Huang, J., Geng, J., Nair, U., Klionsky, D. J. (2006). "Atg22 recycles amino acids to link the degradative and recycling functions of autophagy." Mol Biol Cell 17:5094-5104.17021250
Shimazu, M., Sekito, T., Akiyama, K., Ohsumi, Y., Kakinuma, Y. (2005). "A family of basic amino acid transporters of the vacuolar membrane from Saccharomyces cerevisiae." J Biol Chem 280:4851-4857.15572352
Briza, P., Kalchhauser, H., Pittenauer, E., Allmaier, G., Breitenbach, M. (1996). "N,N'-Bisformyl dityrosine is an in vivo precursor of the yeast ascospore wall." Eur J Biochem 239:124-131.8706696
Iraqui, I., Vissers, S., Cartiaux, M., Urrestarazu, A. (1998). "Characterisation of Saccharomyces cerevisiae ARO8 and ARO9 genes encoding aromatic aminotransferases I and II reveals a new aminotransferase subfamily." Mol Gen Genet 257:238-248.9491083
Castrillo, J. I., Zeef, L. A., Hoyle, D. C., Zhang, N., Hayes, A., Gardner, D. C., Cornell, M. J., Petty, J., Hakes, L., Wardleworth, L., Rash, B., Brown, M., Dunn, W. B., Broadhurst, D., O'Donoghue, K., Hester, S. S., Dunkley, T. P., Hart, S. R., Swainston, N., Li, P., Gaskell, S. J., Paton, N. W., Lilley, K. S., Kell, D. B., Oliver, S. G. (2007). "Growth control of the eukaryote cell: a systems biology study in yeast." J Biol 6:4.17439666

Synthesis Reference:

Enei, Hitoshi; Matsui, Hiroshi; Yamashita, Koichi; Okumura, Shinji; Yamada, Hideaki. Microbiological synthesis of L-tyrosine and 3,4-dihydroxyphenyl-L-alanine. I. Distribution of tyrosine phenol lyase in microorganisms. Agricultural and Biological Chemist

External Links:

Resource	Link
CHEBI ID	17895
HMDB ID	HMDB00158
Pubchem Compound ID	6057
Kegg ID	C00082
ChemSpider ID	5833
FOODB ID	FDB000446
Wikipedia	Tyrosine
BioCyc ID	TYR

Enzymes

Protein Details

1. Tyrosyl-tRNA synthetase, mitochondrial

General function:: Involved in nucleotide binding
Specific function:: Catalyzes the attachment of tyrosine to tRNA(Tyr) in a two-step reaction:tyrosine is first activated by ATP to form Tyr- AMP and then transferred to the acceptor end of tRNA(Tyr)
Gene Name:: MSY1
Uniprot ID:: P48527
Molecular weight:: 55286.89844

Reactions

ATP + L-tyrosine + tRNA(Tyr) → AMP + diphosphate + L-tyrosyl-tRNA(Tyr).

Protein Details

2. Tyrosyl-tRNA synthetase, cytoplasmic

General function:: Involved in nucleotide binding
Specific function:: Catalyzes the attachment of tyrosine to tRNA(Tyr) in a two-step reaction:tyrosine is first activated by ATP to form Tyr- AMP and then transferred to the acceptor end of tRNA(Tyr). The specificity determinants on tRNA(Tyr) are the base pair C1-G72, the discriminator residue A73, and the three anticodon bases G34, U35 and A36. Also involved in nuclear tRNA export
Gene Name:: TYS1
Uniprot ID:: P36421
Molecular weight:: 44019.60156

Reactions

ATP + L-tyrosine + tRNA(Tyr) → AMP + diphosphate + L-tyrosyl-tRNA(Tyr).

Protein Details

3. Aromatic amino acid aminotransferase 2

General function:: Involved in transferase activity, transferring nitrogenous groups
Specific function:: Has aromatic amino acid transaminase activity and kynurenine aminotransferase activity
Gene Name:: ARO9
Uniprot ID:: P38840
Molecular weight:: 58527.0

Reactions

An aromatic amino acid + 2-oxoglutarate → an aromatic oxo acid + L-glutamate.

Protein Details

4. Aromatic amino acid aminotransferase 1

General function:: Involved in transferase activity, transferring nitrogenous groups
Specific function:: Has aromatic amino acid transaminase activity. Also active with methionine, alpha-aminoadipate and leucine when phenylpyruvate is the amino acceptor
Gene Name:: ARO8
Uniprot ID:: P53090
Molecular weight:: 56177.30078

Reactions

An aromatic amino acid + 2-oxoglutarate → an aromatic oxo acid + L-glutamate.
L-2-aminoadipate + 2-oxoglutarate → 2-oxoadipate + L-glutamate

Protein Details

5. Aspartate aminotransferase, mitochondrial

General function:: Involved in transferase activity, transferring nitrogenous groups
Specific function:: Plays a key role in amino acid metabolism. Important for metabolite exchange between mitochondria and cytosol
Gene Name:: AAT1
Uniprot ID:: Q01802
Molecular weight:: 51795.10156

Reactions

L-aspartate + 2-oxoglutarate → oxaloacetate + L-glutamate.

Protein Details

6. Aspartate aminotransferase, cytoplasmic

General function:: Involved in transferase activity, transferring nitrogenous groups
Specific function:: Plays a key role in amino acid metabolism
Gene Name:: AAT2
Uniprot ID:: P23542
Molecular weight:: 46057.30078

Reactions

L-aspartate + 2-oxoglutarate → oxaloacetate + L-glutamate.

Protein Details

7. Spore wall maturation protein DIT1

General function:: Secondary metabolites biosynthesis, transport and catabolism
Specific function:: Involved in spore wall maturation. Catalyzes a two step reaction that leads to the LL-dityrosine containing precursor of the spore wall
Gene Name:: DIT1
Uniprot ID:: P21623
Molecular weight:: 61390.10156

Reactions

Transporters

Protein Details

1. Vacuolar amino acid transporter 3

General function:: Amino acid transport and metabolism
Specific function:: Involved in amino acid efflux from the vacuole to the cytoplasm. Capable of transporting large neutral amino acids including tyrosine, glutamine, asparagine, isoleucine and leucine
Gene Name:: AVT3
Uniprot ID:: P36062
Molecular weight:: 75458.70313

Protein Details

2. Vacuolar amino acid transporter 1

General function:: Amino acid transport and metabolism
Specific function:: Required for the vacuolar uptake of large neutral amino acids including tyrosine, glutamine, asparagine, isoleucine and leucine. Requires ATP for function
Gene Name:: AVT1
Uniprot ID:: P47082
Molecular weight:: 65345.30078

Protein Details

3. General amino-acid permease GAP1

General function:: Involved in transport
Specific function:: Permease for various amino acids as well as for GABA. Can also transport L-cysteine and beta-alanine
Gene Name:: GAP1
Uniprot ID:: P19145
Molecular weight:: 65654.89844

Protein Details

4. Vacuolar amino acid transporter 4

General function:: Amino acid transport and metabolism
Specific function:: Involved in amino acid efflux from the vacuole to the cytoplasm. Capable of transporting large neutral amino acids including tyrosine, glutamine, asparagine, isoleucine and leucine
Gene Name:: AVT4
Uniprot ID:: P50944
Molecular weight:: 80025.0

Protein Details

5. Tryptophan permease

General function:: Involved in transport
Specific function:: Required for high-affinity tryptophan transport. Also transports cysteine, phenyalanine and tyrosine
Gene Name:: TAT2
Uniprot ID:: P38967
Molecular weight:: 65403.80078

Protein Details

6. Leu/Val/Ile amino-acid permease

General function:: Involved in transport
Specific function:: Permease for leucine, valine and isoleucine. Also transports cysteine, methionine, phenyalanine, tyrosine and tryptophan
Gene Name:: BAP2
Uniprot ID:: P38084
Molecular weight:: 67669.60156

Protein Details

7. Valine/tyrosine/tryptophan amino-acid permease 1

General function:: Involved in transport
Specific function:: High-affinity transport of valine and tyrosine. Low- affinity transport of tryptophan. Can also transport L-cysteine
Gene Name:: TAT1
Uniprot ID:: P38085
Molecular weight:: 68756.89844

Protein Details

8. Valine amino-acid permease

General function:: Involved in transport
Specific function:: Involved in transport of isoleucine, leucine, valine, cysteine, methionine, phenylalanine, tyrosine and tryptophan
Gene Name:: BAP3
Uniprot ID:: P41815
Molecular weight:: 67364.39844

Protein Details

9. Autophagy-related protein 22

General function:: Involved in amino acid export from vacuole
Specific function:: Required for lysis of autophagic vesicles after delivery to the vacuole
Gene Name:: ATG22
Uniprot ID:: P25568
Molecular weight:: 58843.10156

Protein Details

10. General amino acid permease AGP1

General function:: Involved in transport
Specific function:: Broad substrate range permease which transports asparagine and glutamine with intermediate specificity. Also transports Ala, Cys, Gly, Ile, Leu, Met, Phe, Ser, Thr, Tyr and Val. Important for the utilization of amino acids as a nitrogen source
Gene Name:: AGP1
Uniprot ID:: P25376
Molecular weight:: 69670.70313

Protein Details

11. Vacuolar basic amino acid transporter 2

General function:: Involved in transmembrane transport
Specific function:: Transporter required for vacuolar uptake of histidine, arginine and lysine and to a lesser extent tyrosine
Gene Name:: VBA2
Uniprot ID:: P38358
Molecular weight:: 51676.39844

Structure for #<Compound:0xa6e88220>

Enzymes

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Transporters