L-Isoleucine (YMDB00038)

Identification

YMDB ID

YMDB00038

Name

L-Isoleucine

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

Isoleucine (abbreviated as Ile or I) 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 branched chain amino acid, because of the hydrophobic nature of the branched alkyl side chain. Together with threonine, isoleucine is one of two common amino acids that have a chiral side chain. it is synthesized via several steps, starting from pyruvic acid and alpha-ketoglutarate. Enzymes involved in this biosynthesis include: Acetolactate synthase (also known as acetohydroxy acid synthase), Acetohydroxy acid isomeroreductase, Dihydroxyacid dehydratase and Valine aminotransferase.
S. cerevisiae degrade 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. Each of the three steps in branched-chain amino acid degradation can be catalyzed by more than one isozyme; which enzyme is used appears to depend on the amino acid, the carbon source and the stage of growth of the culture. The initial transamination step in isoleucine degradation can be catalyzed by either of the branched-chain amino acid transaminases BAT1 (mitochondrial) or BAT2 (cytosolic). The subsequent decarboxylation step can be catalyzed by any one of the five decarboxylases (Pdc1p, Pdc5p, Pdc6p, Thi3p, and Aro10p) and the final step can be catalyzed by any one of six alcohol dehydrogenases (Adh1p, Adh2p, Adh3p, Adh4p, Adh5p, and Sfa1p).

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

(2S,3S)-2-amino-3-methyl-Pentanoate
(2S,3S)-2-amino-3-methyl-Pentanoic acid
(2S,3S)-2-Amino-3-methylpentanoate
(2S,3S)-2-Amino-3-methylpentanoic acid
(2S,3S)-a-Amino-b-methyl-n-valerate
(2S,3S)-a-Amino-b-methyl-n-valeric acid
(2S,3S)-a-Amino-b-methylvalerate
(2S,3S)-a-Amino-b-methylvaleric acid
(2S,3S)-alph-Amino-beta-methylvalerate
(2S,3S)-alph-Amino-beta-methylvaleric acid
(2S,3S)-alpha-Amino-beta-merthyl-n-valerate
(2S,3S)-alpha-Amino-beta-merthyl-n-valeric acid
(2S,3S)-alpha-Amino-beta-merthylvalerate
(2S,3S)-alpha-Amino-beta-merthylvaleric acid
(2S,3S)-alpha-Amino-beta-methyl-n-valerate
(2S,3S)-alpha-Amino-beta-methyl-n-valeric acid
(2S,3S)-alpha-Amino-beta-methylvalerate
(2S,3S)-alpha-Amino-beta-methylvaleric acid
(S,S)-Isoleucine
(S)-Isoleucine
[S-(R*,R*)]-2-Amino-3-methylpentanoate
[S-(R*,R*)]-2-Amino-3-methylpentanoic acid
2-Amino-3-methylpentanoate
2-Amino-3-methylpentanoic acid
2-Amino-3-methylvalerate
2-Amino-3-methylvaleric acid
2S,3S-Isoleucine
a-amino-b-Methylvalerate
a-amino-b-Methylvaleric acid
Alloisoleucine
alpha-amino-beta-Methylvalerate
alpha-amino-beta-Methylvaleric acid
erythro-L-Isoleucine
I
Ile
iso-leucine
Isoleucine
Isoleucine, L isomer
Isoleucine, L-isomer
L-(+)-Isoleucine
L-Ile
L-Isomer isoleucine
α-amino-β-methylvalerate
α-amino-β-methylvaleric acid
2S-Amino-3S-methylpentanoate
L-Isoleucine

CAS number

73-32-5

Weight

Average: 131.1729
Monoisotopic: 131.094628665

InChI Key

AGPKZVBTJJNPAG-WHFBIAKZSA-N

InChI

InChI=1S/C6H13NO2/c1-3-4(2)5(7)6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9)/t4-,5-/m0/s1

IUPAC Name

(2S,3S)-2-amino-3-methylpentanoic acid

Traditional IUPAC Name

L-isoleucine

Chemical Formula

C₆H₁₃NO₂

SMILES

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

Chemical Taxonomy

Description

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

Isoleucine and derivatives

Alternative Parents

Substituents

Isoleucine or derivatives
Alpha-amino acid
L-alpha-amino acid
Branched fatty acid
Methyl-branched fatty acid
Fatty acid
Fatty acyl
Amino acid
Monocarboxylic acid or derivatives
Carboxylic acid
Organic oxide
Organopnictogen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Carbonyl group
Organic oxygen compound
Amine
Organic nitrogen compound
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

aspartate family amino acid (CHEBI:17191 )
proteinogenic amino acid (CHEBI:17191 )
L-alpha-amino acid (CHEBI:17191 )
isoleucine (CHEBI:17191 )
Common amino acids (C00407 )
Amino fatty acids (LMFA01100047 )

Physical Properties

State

Solid

Charge

Melting point

285.5 °C

Experimental Properties

Property	Value	Reference
Water Solubility	34.4 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]	PhysProp
LogP	-1.70 [HANSCH,C ET AL. (1995)]	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	114 g/L	ALOGPS
logP	-1.7	ALOGPS
logP	-1.5	ChemAxon
logS	-0.06	ALOGPS
pKa (Strongest Acidic)	2.79	ChemAxon
pKa (Strongest Basic)	9.59	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	34.09 m³·mol⁻¹	ChemAxon
Polarizability	14.11 Å³	ChemAxon
Number of Rings	0	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
vacuole
cytoplasm

Organoleptic Properties

Flavour/Odour	Source
Bitter	FDB012397
Odorless	FDB012397

SMPDB Pathways

Isoleucine degradation	PW002491
isoleucine biosynthesis	PW002476

KEGG Pathways

Valine, leucine and isoleucine biosynthesis	ec00290
Valine, leucine and isoleucine degradation	ec00280

SMPDB Reactions

KEGG Reactions

Oxoglutaric acid + L-Isoleucine ↔ L-Glutamic acid + (S)-3-methyl-2-oxovaleric acid

Adenosine triphosphate + tRNA(Ile) + L-Isoleucine → Adenosine monophosphate + Pyrophosphate + Ile-tRNA(Ile)

Concentrations

Intracellular Concentrations

Intracellular Concentration	Substrate	Growth Conditions	Strain	Citation
938 ± 19 µM	YPD media	aerobic	Baker's yeast	PMID: 7654310
156 ± 3 µM	YPG media	aerobic	Baker's yeast	PMID: 7654310
235 ± 5 µM	SD media	aerobic	Baker's yeast	PMID: 7654310
156 ± 3 µM	SG media	aerobic	Baker's yeast	PMID: 7654310
626 ± 12 µM	M (molasses)	aerobic	Baker's yeast	PMID: 7654310
4535 ± 91 µM	MA (molasses)	aerobic	Baker's yeast	PMID: 7654310
1173 ± 23 µM	MB (molasses)	aerobic	Baker's yeast	PMID: 7654310
6177 ± 123 µM	MAB (molasses)	aerobic	Baker's yeast	PMID: 7654310
1359 ± 68 µM	YEB media with 0.5 mM glucose	aerobic	Baker's yeast	Experimentally Determined Not Available
700 ± 67 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)	splash10-0a4i-0930000000-e78f845bb2a8d4736476	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-0a4i-0910000000-de9162d149073d0e2a37	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-0a4i-0920000000-599e61f8ccdb6525c7a9	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0a4i-0910000000-742e44c426c0d6c2a9ac	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-05fr-8910000000-dbb33e0f02ac2ca5fedd	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-0920000000-37690f426455ac41e2c2	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4i-0930000000-e78f845bb2a8d4736476	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4i-0910000000-de9162d149073d0e2a37	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4i-0920000000-599e61f8ccdb6525c7a9	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4i-0910000000-742e44c426c0d6c2a9ac	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-QQ (Non-derivatized)	splash10-0udi-2392000000-74cca1eb265b8e3d7f43	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-05fr-8910000000-dbb33e0f02ac2ca5fedd	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-000i-9100000000-27891dff695c5db53796	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4i-0910000000-43ec1890f6dbd6aea657	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00b9-9100000000-40bc9ef43da5f18be883	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-000i-9200000000-ae8694c0f3e4dcc608f9	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)	splash10-000i-9300000000-8a23b3e62231eb65f80f	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00ko-9000000000-ac7e71578d7e1d0e8ce9	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-052f-9000000000-2586d4a089921dd977ed	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0900000000-5b11521ff6a631376d2b	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-9000000000-3c352f229e4067fcd489	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-9000000000-8a7ef48fc0c1b6f845c2	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0002-0920000000-2e11aa1c7a5defc386db	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0900000000-b63ac9cf06eda4c54a81	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-9000000000-e5b0c8c6b09f541d6dbf	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-9000000000-d89d16d5c2242e44ec63	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-9000000000-5de583142c7bdb381c8f	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-001i-0900000000-8c75bde35c4a4073ee65	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-001i-0900000000-233a9862f616afea2d17	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-001i-1900000000-375f35065b82b13e6d6e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-00dl-9000000000-d0d4a9f90fe2aca74483	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0006-9000000000-0018f47571feaf232ff8	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-001r-7900000000-278dc67396114be331ba	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-000i-9000000000-e26c042aa6231eeca071	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-014r-9000000000-b6c1752fd3fbccb3d1c5	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-05mo-9000000000-0569c3162621252ed0a8	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-052f-9000000000-3d52b5d56d3fab45276e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - CE-ESI-TOF (CE-system connected to 6210 Time-of-Flight MS, Agilent) , Positive	splash10-001i-0900000000-720554d58264a9cfdb67	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0019-9500000000-00268b2694cde281641b	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-9000000000-4014793e17e0290790a4	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-eb9a97a14461e524e76e	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	splash10-004r-9000000000-34d4d4cb7042da231eb4	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
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
Eden, A., Van Nedervelde, L., Drukker, M., Benvenisty, N., Debourg, A. (2001). "Involvement of branched-chain amino acid aminotransferases in the production of fusel alcohols during fermentation in yeast." Appl Microbiol Biotechnol 55:296-300.11341309
Freist, W., von der Haar, F., Cramer, F. (1981). "Isoleucyl-tRNA synthetase from Baker's yeast. Action of ATP analogs in pyrophosphate exchange and aminoacylation, two pathways of the aminoacylation depending on concentration of pyrophosphate." Eur J Biochem 119:151-164.6281001
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
Tzagoloff, A., Shtanko, A. (1995). "Mitochondrial and cytoplasmic isoleucyl-, glutamyl- and arginyl-tRNA synthetases of yeast are encoded by separate genes." Eur J Biochem 230:582-586.7607232
Kispal, G., Steiner, H., Court, D. A., Rolinski, B., Lill, R. (1996). "Mitochondrial and cytosolic branched-chain amino acid transaminases from yeast, homologs of the myc oncogene-regulated Eca39 protein." J Biol Chem 271:24458-24464.8798704
Harris, C. L., Kolanko, C. J. (1995). "Aminoacyl-tRNA synthetase complex in Saccharomyces cerevisiae." Biochem J 309 ( Pt 1):321-324.7619074
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:

Marvel, C. S. L-Isoleucine. Organic Syntheses (1941), 21 60-4.

External Links:

Resource	Link
CHEBI ID	17191
HMDB ID	HMDB00172
Pubchem Compound ID	791
Kegg ID	C00407
ChemSpider ID	6067
FOODB ID	FDB012397
Wikipedia	Isoleucine
BioCyc ID	ILE

Enzymes

Protein Details

1. Branched-chain-amino-acid aminotransferase, cytosolic

General function:: Involved in catalytic activity
Specific function:: Catalyzes the first reaction in the catabolism of the essential branched chain amino acids leucine, isoleucine, and valine. Involved in cell cycle regulation
Gene Name:: BAT2
Uniprot ID:: P47176
Molecular weight:: 41624.39844

Reactions

L-leucine + 2-oxoglutarate → 4-methyl-2-oxopentanoate + L-glutamate.
2-oxoglutaric acid + L-isoleucine → (S)-3-methyl-2-oxopentanoic acid + L-glutamic acid.
2-oxoglutaric acid + L-valine → 3-methyl-2-oxobutanoic acid + L-glutamic acid.

Protein Details

2. Isoleucyl-tRNA synthetase, mitochondrial

General function:: Involved in nucleotide binding
Specific function:: ATP + L-isoleucine + tRNA(Ile) = AMP + diphosphate + L-isoleucyl-tRNA(Ile)
Gene Name:: ISM1
Uniprot ID:: P48526
Molecular weight:: 115793.0

Reactions

ATP + L-isoleucine + tRNA(Ile) → AMP + diphosphate + L-isoleucyl-tRNA(Ile).

Protein Details

3. Branched-chain-amino-acid aminotransferase, mitochondrial

General function:: Involved in catalytic activity
Specific function:: Catalyzes the first reaction in the catabolism of the essential branched chain amino acids leucine, isoleucine, and valine. Appears to be involved in the regulation of the transition from G1 to S phase in the cell cycle. High copy suppressor of a temperature-sensitive mutation in the ABC transporter, ATM1
Gene Name:: BAT1
Uniprot ID:: P38891
Molecular weight:: 43595.69922

Reactions

L-leucine + 2-oxoglutarate → 4-methyl-2-oxopentanoate + L-glutamate.
2-oxoglutaric acid + L-isoleucine → (S)-3-methyl-2-oxopentanoic acid + L-glutamic acid.
2-oxoglutaric acid + L-valine → 3-methyl-2-oxobutanoic acid + L-glutamic acid.

Protein Details

4. Isoleucyl-tRNA synthetase, cytoplasmic

General function:: Involved in nucleotide binding
Specific function:: ATP + L-isoleucine + tRNA(Ile) = AMP + diphosphate + L-isoleucyl-tRNA(Ile)
Gene Name:: ILS1
Uniprot ID:: P09436
Molecular weight:: 122982.0

Reactions

ATP + L-isoleucine + tRNA(Ile) → AMP + diphosphate + L-isoleucyl-tRNA(Ile).

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. 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

6. 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

7. 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

8. 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

9. 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:0xb1079dcc>

Enzymes

Reactions

Reactions

Reactions

Reactions

Transporters