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Identification
YMDB IDYMDB00038
NameL-Isoleucine
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionIsoleucine (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
Thumb
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
  • Α-amino-β-methylvalerate
  • Α-amino-β-methylvaleric acid
  • 2S-Amino-3S-methylpentanoate
  • L-Isoleucine
CAS number73-32-5
WeightAverage: 131.1729
Monoisotopic: 131.094628665
InChI KeyAGPKZVBTJJNPAG-WHFBIAKZSA-N
InChIInChI=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 NameL-isoleucine
Chemical FormulaC6H13NO2
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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentIsoleucine 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 FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting point285.5 °C
Experimental Properties
PropertyValueReference
Water Solubility34.4 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogP-1.70 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility114 g/LALOGPS
logP-1.7ALOGPS
logP-1.5ChemAxon
logS-0.06ALOGPS
pKa (Strongest Acidic)2.79ChemAxon
pKa (Strongest Basic)9.59ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity34.09 m³·mol⁻¹ChemAxon
Polarizability14.11 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • extracellular
  • mitochondrion
  • vacuole
  • cytoplasm
Organoleptic Properties
Flavour/OdourSource
BitterFDB012397
OdorlessFDB012397
SMPDB Pathways
Isoleucine degradationPW002491 ThumbThumb?image type=greyscaleThumb?image type=simple
isoleucine biosynthesisPW002476 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Valine, leucine and isoleucine biosynthesisec00290 Map00290
Valine, leucine and isoleucine degradationec00280 Map00280
SMPDB Reactions
(S)-3-methyl-2-oxovaleric acid + L-Glutamic acidOxoglutaric acid + L-Isoleucine
L-Isoleucine + Oxoglutaric acidL-Glutamic acid + (S)-3-methyl-2-oxovaleric acid
L-Isoleucine + hydronCarbon dioxide + (S)-3-methyl-2-oxovaleric acid
L-Isoleucine + Adenosine triphosphate + waterL-Isoleucine + ADP + phosphate + hydron
L-Isoleucine + Adenosine triphosphate + waterL-Isoleucine + ADP + phosphate + hydron
KEGG Reactions
Oxoglutaric acid + L-IsoleucineL-Glutamic acid + (S)-3-methyl-2-oxovaleric acid
Adenosine triphosphate + tRNA(Ile) + L-IsoleucineAdenosine monophosphate + Pyrophosphate + Ile-tRNA(Ile)
Concentrations
Intracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
938 ± 19 µM YPD mediaaerobicBaker's yeastPMID: 7654310
156 ± 3 µM YPG mediaaerobicBaker's yeastPMID: 7654310
235 ± 5 µM SD mediaaerobicBaker's yeastPMID: 7654310
156 ± 3 µM SG mediaaerobicBaker's yeastPMID: 7654310
626 ± 12 µM M (molasses)aerobicBaker's yeastPMID: 7654310
4535 ± 91 µM MA (molasses)aerobicBaker's yeastPMID: 7654310
1173 ± 23 µM MB (molasses)aerobicBaker's yeastPMID: 7654310
6177 ± 123 µM MAB (molasses)aerobicBaker's yeastPMID: 7654310
1359 ± 68 µM YEB media with 0.5 mM glucoseaerobicBaker's yeastExperimentally Determined
Not Available
700 ± 67 µM Synthetic medium with 20 g/L glucoseaerobicBaker's yeastPMID: 12584756
Conversion Details Here
Extracellular ConcentrationsNot Available
Spectra
Spectra
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:
ResourceLink
CHEBI ID17191
HMDB IDHMDB00172
Pubchem Compound ID791
Kegg IDC00407
ChemSpider ID6067
FOODB IDFDB012397
WikipediaIsoleucine
BioCyc IDILE

Enzymes

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.
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).
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.
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

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
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
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
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
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
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
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
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
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