L-Phenylalanine (YMDB00304)

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Identification

YMDB ID

YMDB00304

Name

L-Phenylalanine

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

Phenylalanine (abbreviated as Phe or F) 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 benzyl side chain. L-Phenylalanine (LPA) is an electrically neutral amino acid. It is used in the manufacture of food and drink products and sold as a nutritional supplement for its reputed analgesic and antidepressant effects. 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. Phenylalanine normally has only three metabolic fates: incorporation into polypeptide chains, production of tyrosine via the tetrahydrobiopterin-requiring phenylalanine hydroxylase and conversion to a fusel alcohol. S. cerevisiae degrade the aromatic amino acids (tryptophan, phenylalanine, and tyrosine) and the branched-chain amino acids (valine, leucine, and iso-leucine) 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.

Structure

MOL SDF PDB SMILES InChI

Synonyms

(-)-beta-Phenylalanine
(L)-Phenylalanine
(S)-(-)-Phenylalanine
(S)-2-amino-3-phenylpropanoate
(S)-2-amino-3-phenylpropanoic acid
(S)-2-Amino-3-phenylpropionate
(S)-2-Amino-3-phenylpropionic acid
(S)-alpha-Amino-benzenepropanoate
(S)-alpha-Amino-benzenepropanoic acid
(S)-alpha-Amino-beta-phenylpropionate
(S)-alpha-Amino-beta-phenylpropionic acid
(S)-alpha-Aminobenzenepropanoate
(S)-alpha-Aminobenzenepropanoic acid
(S)-alpha-Aminohydrocinnamate
(S)-alpha-Aminohydrocinnamic acid
(S)-Phenylalanine
3-Phenyl-L-alanine
alpha-Aminohydrocinnamate
alpha-Aminohydrocinnamic acid
beta-Phenyl-alpha-alanine
beta-Phenyl-L-alanine
beta-Phenylalanine
L-2-Amino-3-phenylpropionate
L-2-Amino-3-phenylpropionic acid
Phe
phenyl-Alanine
Phenylalamine
Phenylalanine
F
(S)-a-Amino-b-phenylpropionate
(S)-a-Amino-b-phenylpropionic acid
(S)-Α-amino-β-phenylpropionate
(S)-Α-amino-β-phenylpropionic acid
b-Phenyl-L-alanine
Β-phenyl-L-alanine
L-Isomer phenylalanine
Phenylalanine, L isomer
Phenylalanine, L-isomer
Endorphenyl
(6S)-Tetrahydrofolate
(6S)-Tetrahydrofolic acid
(6S)-THFA
5,6,7,8-Tetrahydrofolate
Tetrahydrofolate
THF
5,6,7,8-Tetrahydrofolic acid

CAS number

63-91-2

Weight

Average: 165.1891
Monoisotopic: 165.078978601

InChI Key

COLNVLDHVKWLRT-QMMMGPOBSA-N

InChI

InChI=1S/C9H11NO2/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8H,6,10H2,(H,11,12)/t8-/m0/s1

IUPAC Name

(2S)-2-amino-3-phenylpropanoic acid

Traditional IUPAC Name

L-phenylalanine

Chemical Formula

C₉H₁₁NO₂

SMILES

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

Chemical Taxonomy

Description

belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine 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

Phenylalanine and derivatives

Alternative Parents

Substituents

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

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

proteinogenic amino acid (CHEBI:17295 )
L-alpha-amino acid (CHEBI:17295 )
phenylalanine (CHEBI:17295 )
erythrose 4-phosphate/phosphoenolpyruvate family amino acid (CHEBI:17295 )
Common amino acids (C00079 )

Physical Properties

State

Solid

Charge

Melting point

283 °C

Experimental Properties

Property	Value	Reference
Water Solubility	26.9 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]	PhysProp
LogP	-1.38 [AVDEEF,A (1997)]	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	4.14 g/L	ALOGPS
logP	-1.4	ALOGPS
logP	-1.2	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	2.47	ChemAxon
pKa (Strongest Basic)	9.45	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	63.32 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	45.12 m³·mol⁻¹	ChemAxon
Polarizability	17.03 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
cytoplasm

Organoleptic Properties

Flavour/Odour	Source
Bitter	FDB004940
Odorless	FDB004940

SMPDB Pathways

Methionine metabolism and salvage	PW002384
Phenylalanine metabolism	PW002437
Tryptophan metabolism	PW002442

KEGG Pathways

Phenylalanine metabolism	ec00360
Phenylalanine, tyrosine and tryptophan biosynthesis	ec00400
Tryptophan metabolism	ec00380

SMPDB Reactions

4-Methylthio-2-oxobutanoate + L-Phenylalanine → L-Methionine + 2-Ketobutyric acid

keto-phenylpyruvic acid + L-Alanine ↔ Pyruvic acid + L-Phenylalanine

L-Tryptophan + keto-phenylpyruvic acid → 3-(indol-3-yl)pyruvate + L-Phenylalanine

keto-phenylpyruvic acid + L-Glutamic acid → L-Phenylalanine + Oxoglutaric acid

KEGG Reactions

Oxoglutaric acid + L-Phenylalanine ↔ L-Glutamic acid + keto-phenylpyruvic acid

tRNA(Phe) + Adenosine triphosphate + L-Phenylalanine → Adenosine monophosphate + Pyrophosphate + Phe-tRNA(Phe)

Concentrations

Intracellular Concentrations

Intracellular Concentration	Substrate	Growth Conditions	Strain	Citation
1428 ± 29 µM	YPD media	aerobic	Baker's yeast	PMID: 7654310
1180 ± 23 µM	YPG media	aerobic	Baker's yeast	PMID: 7654310
311 ± 6 µM	SD media	aerobic	Baker's yeast	PMID: 7654310
186 ± 4 µM	SG media	aerobic	Baker's yeast	PMID: 7654310
683 ± 14 µM	M (molasses)	aerobic	Baker's yeast	PMID: 7654310
2794 ± 56 µM	MA (molasses)	aerobic	Baker's yeast	PMID: 7654310
993 ± 20 µM	MB (molasses)	aerobic	Baker's yeast	PMID: 7654310
3042 ± 61 µM	MAB (molasses)	aerobic	Baker's yeast	PMID: 7654310
1415 ± 71 µM	YEB media with 0.5 mM glucose	aerobic	Baker's yeast	Experimentally Determined Not Available
540 ± 64 µM	Synthetic medium with 20 g/L glucose	aerobic	Baker's yeast	PMID: 12584756
Conversion Details Here

Extracellular Concentrations

Not Available

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) (2 TMS)	splash10-0fr6-1930000000-a37fbccaf826443ef70c	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-014l-1940000000-537e2725d621246630c1	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-00di-9630000000-ead0919f9a19d2352d80	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-00di-2900000000-cb2d6dc4bf9515150328	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-014l-2960000000-f77489792f0652dd5613	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014l-0970000000-792b341dd28b9e30bac2	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0fr6-1930000000-a37fbccaf826443ef70c	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014l-1940000000-537e2725d621246630c1	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-QQ (Non-derivatized)	splash10-0ul9-3659000000-b85be4e71798e2fdc47b	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9630000000-ead0919f9a19d2352d80	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00di-2900000000-cb2d6dc4bf9515150328	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-014l-2960000000-f77489792f0652dd5613	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-9600000000-df38fcb743d8f44fb876	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00di-7900000000-f21569d2ec75b88e1bda	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 (Non-derivatized) - 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 (TBDMS_1_1) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-014i-0900000000-0f3b994108b8a9fd2a56	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0gb9-2900000000-c14d44c8a67621757f3d	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-004i-9300000000-08c642dab7f49c00da43	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-014i-0900000000-7dce1e473976f7d2143e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0f6x-9600000000-711557391093b0d8500a	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-00di-0900000000-0c25a5c116eac7bb059b	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-00di-0900000000-2804f79084ac4e67e155	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-014i-0900000000-8a71bb1f8424064d7caf	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0f6x-9800000000-e027ff6bb67ce55e80a5	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-014i-0900000000-9f6185e9c7d54189f369	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-00di-0900000000-df5f72fe2bba91742427	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0ir3-0988735721-bac229222fe7b52812a8	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0002-0900000000-453477dec847a3672ffe	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0a4i-0010963000-079a66bf710f6778bceb	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-00di-0000009000-62dbe98de4ecde484fb3	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-03di-0900000000-80558c17dc1845663c85	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0002-3900000000-e1ee31d41e48824e84b7	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0f6x-9500000000-cc11290a37615f24e16e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0006-9000000000-1a6020bce0e1a9a14832	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0006-9000000000-38c044a112152626962e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-014i-0900000000-9b908abfcb63153d60b3	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-00di-1900000000-3ba5964e151bb1d56188	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-00di-2900000000-20a7d24da0281f5b3b78	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-0udi-5900000000-1800642a835b49f3398a	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-0fb9-9300000000-f262384c85fb843f8a11	JSpectraViewer \| MoNA
MS	Mass Spectrum (Electron Ionization)	splash10-00dl-9300000000-4782928378caea601f9b	JSpectraViewer \| MoNA
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
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
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
Vuralhan, Z., Morais, M. A., Tai, S. L., Piper, M. D., Pronk, J. T. (2003). "Identification and characterization of phenylpyruvate decarboxylase genes in Saccharomyces cerevisiae." Appl Environ Microbiol 69:4534-4541.12902239
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
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
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:

Zhou, Hua; Zhong, Yao; Sun, Guanghai; Wei, Ping. Preparation of L-phenylalanine by an aqueous two-phase system. Huaxue Fanying Gongcheng Yu Gongyi (2006), 22(2), 146-150.

External Links:

Resource	Link
CHEBI ID	17295
HMDB ID	HMDB00159
Pubchem Compound ID	6140
Kegg ID	C00079
ChemSpider ID	5910
FOODB ID	FDB004940
Wikipedia	Phenylalanine
BioCyc ID	PHE

Enzymes

Protein Details

1. Phenylalanyl-tRNA synthetase, mitochondrial

General function:: Involved in nucleotide binding
Specific function:: Catalyzes direct attachment of p-Tyr (Tyr) to tRNAPhe. Permits also, with a lower efficiency, the attachment of m-Tyr to tRNAPhe, thereby opening the way for delivery of the misacylated tRNA to the ribosome and incorporation of ROS-damaged amino acid into proteins
Gene Name:: MSF1
Uniprot ID:: P08425
Molecular weight:: 54828.39844

Reactions

ATP + L-phenylalanine + tRNA(Phe) → AMP + diphosphate + L-phenylalanyl-tRNA(Phe).

Protein Details

2. Phenylalanyl-tRNA synthetase beta chain

General function:: Involved in RNA binding
Specific function:: ATP + L-phenylalanine + tRNA(Phe) = AMP + diphosphate + L-phenylalanyl-tRNA(Phe)
Gene Name:: FRS1
Uniprot ID:: P15624
Molecular weight:: 67364.29688

Reactions

ATP + L-phenylalanine + tRNA(Phe) → AMP + diphosphate + L-phenylalanyl-tRNA(Phe).

Protein Details

3. Phenylalanyl-tRNA synthetase alpha chain

General function:: Involved in nucleotide binding
Specific function:: ATP + L-phenylalanine + tRNA(Phe) = AMP + diphosphate + L-phenylalanyl-tRNA(Phe)
Gene Name:: FRS2
Uniprot ID:: P15625
Molecular weight:: 57511.0

Reactions

ATP + L-phenylalanine + tRNA(Phe) → AMP + diphosphate + L-phenylalanyl-tRNA(Phe).

Protein Details

4. 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

5. 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

Transporters

Protein Details

1. 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

2. 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

3. 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

4. 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

5. 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

Structure for #<Compound:0xae488e34>

Enzymes

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Transporters