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Identification
YMDB IDYMDB00387
NameL-Leucine
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionLeucine (abbreviated as Leu or L) 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 its branched alkyl side chain. Leucine is synthesized in yeast via several steps starting from pyruvic acid. The initial part of the pathway also leads to valine. The intermediate alpha-ketoisovalerate is converted to alpha-isopropylmalate and then β-isopropylmalate, which is dehydrogenated to alpha-ketoisocaproate, which in the final step undergoes reductive amination. Enzymes involved in leucine biosynthesis include: 1) Acetolactate synthase; 2) Acetohydroxy acid isomeroreductase; 3) Dihydroxyacid dehydratase; 4) alpha-Isopropylmalate synthase; 5) alpha-Isopropylmalate isomerase, and 6) Leucine 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. In leucine degradation, Thi3p is believed to be the major decarboxylase.
Structure
Thumb
Synonyms
  • (2S)-2-Amino-4-methylpentanoate
  • (2S)-2-Amino-4-methylpentanoic acid
  • (S)-(+)-Leucine
  • (S)-2-Amino-4-methylpentanoate
  • (S)-2-Amino-4-methylpentanoic acid
  • (S)-2-Amino-4-methylvalerate
  • (S)-2-Amino-4-methylvaleric acid
  • (S)-Leucine
  • 4-methyl-L-Norvaline
  • L-(+)-Leucine
  • L-a-Aminoisocaproate
  • L-a-Aminoisocaproic acid
  • L-alpha-Aminoisocaproate
  • L-alpha-Aminoisocaproic acid
  • Leu
  • Leucine
  • (2S)-alpha-2-Amino-4-methylvaleric acid
  • (2S)-alpha-Leucine
  • 2-Amino-4-methylvaleric acid
  • L
  • L-Leucin
  • L-Leuzin
  • (2S)-a-2-Amino-4-methylvalerate
  • (2S)-a-2-Amino-4-methylvaleric acid
  • (2S)-alpha-2-Amino-4-methylvalerate
  • (2S)-Α-2-amino-4-methylvalerate
  • (2S)-Α-2-amino-4-methylvaleric acid
  • (2S)-a-Leucine
  • (2S)-Α-leucine
  • 2-Amino-4-methylvalerate
  • Leucine, L-isomer
  • L-Isomer leucine
  • Leucine, L isomer
CAS number61-90-5
WeightAverage: 131.1729
Monoisotopic: 131.094628665
InChI KeyROHFNLRQFUQHCH-YFKPBYRVSA-N
InChIInChI=1S/C6H13NO2/c1-4(2)3-5(7)6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9)/t5-/m0/s1
IUPAC Name(2S)-2-amino-4-methylpentanoic acid
Traditional IUPAC NameL-leucine
Chemical FormulaC6H13NO2
SMILES[H]OC(=O)[C@@]([H])(N([H])[H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as leucine and derivatives. Leucine and derivatives are compounds containing leucine or a derivative thereof resulting from reaction of leucine 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 ParentLeucine and derivatives
Alternative Parents
Substituents
  • Leucine 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 point268-288 °C
Experimental Properties
PropertyValueReference
Water Solubility21.5 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogP-1.52 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility69.8 g/LALOGPS
logP-1.8ALOGPS
logP-1.6ChemAxon
logS-0.27ALOGPS
pKa (Strongest Acidic)2.79ChemAxon
pKa (Strongest Basic)9.52ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity34.17 m³·mol⁻¹ChemAxon
Polarizability14.16 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
BitterFDB000899
OdorlessFDB000899
SMPDB Pathways
Leucine BiosynthesisPW002475 ThumbThumb?image type=greyscaleThumb?image type=simple
Leucine DegradationPW002490 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Valine, leucine and isoleucine biosynthesisec00290 Map00290
Valine, leucine and isoleucine degradationec00280 Map00280
SMPDB Reactions
Ketoleucine + L-Glutamic acidOxoglutaric acid + L-Leucine
L-Leucine + Oxoglutaric acidL-Glutamic acid + Ketoleucine
L-Leucine + Oxoglutaric acidL-Glutamic acid + Ketoleucine
KEGG Reactions
L-Leucine + Oxoglutaric acidKetoleucine + L-Glutamic acid
L-Leucine + Adenosine triphosphate + tRNA(Leu) → Adenosine monophosphate + Pyrophosphate + Leu-tRNA(Leu)
Concentrations
Intracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
1486 ± 30 µM YPD mediaaerobicBaker's yeastPMID: 7654310
626 ± 12 µM YPG mediaaerobicBaker's yeastPMID: 7654310
391 ± 8 µM SD mediaaerobicBaker's yeastPMID: 7654310
235 ± 5 µM SG mediaaerobicBaker's yeastPMID: 7654310
782 ± 16 µM M (molasses)aerobicBaker's yeastPMID: 7654310
2658 ± 53 µM MA (molasses)aerobicBaker's yeastPMID: 7654310
547 ± 11 µM MB (molasses)aerobicBaker's yeastPMID: 7654310
2580 ± 52 µM MAB (molasses)aerobicBaker's yeastPMID: 7654310
2878 ± 144 µM YEB media with 0.5 mM glucoseaerobicBaker's yeastExperimentally Determined
Not Available
470 ± 174 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
  • 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
  • Dickinson, J. R., Harrison, S. J., Hewlins, M. J. (1998). "An investigation of the metabolism of valine to isobutyl alcohol in Saccharomyces cerevisiae." J Biol Chem 273:25751-25756.9748245
  • 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
  • Dickinson, J. R., Lanterman, M. M., Danner, D. J., Pearson, B. M., Sanz, P., Harrison, S. J., Hewlins, M. J. (1997). "A 13C nuclear magnetic resonance investigation of the metabolism of leucine to isoamyl alcohol in Saccharomyces cerevisiae." J Biol Chem 272:26871-26878.9341119
  • 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:Leuchtenberger, Wolfgang; Karrenbauer, Michael; Ploecker, Ulf. Scale-up of an enzyme membrane reactor process for the manufacture of L-enantiomeric compounds. Annals of the New York Academy of Sciences (1984), 434(Enzyme Eng.), 78-86.
External Links:
ResourceLink
CHEBI ID15603
HMDB IDHMDB00687
Pubchem Compound ID6106
Kegg IDC00123
ChemSpider ID5880
FOODB IDFDB000899
WikipediaLeucine
BioCyc IDLEU

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 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-leucine + tRNA(Leu) = AMP + diphosphate + L-leucyl-tRNA(Leu)
Gene Name:
CDC60
Uniprot ID:
P26637
Molecular weight:
124140.0
Reactions
ATP + L-leucine + tRNA(Leu) → AMP + diphosphate + L-leucyl-tRNA(Leu).
General function:
Involved in nucleotide binding
Specific function:
ATP + L-leucine + tRNA(Leu) = AMP + diphosphate + L-leucyl-tRNA(Leu)
Gene Name:
NAM2
Uniprot ID:
P11325
Molecular weight:
101920.0
Reactions
ATP + L-leucine + tRNA(Leu) → AMP + diphosphate + L-leucyl-tRNA(Leu).

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:
Involved in transport
Specific function:
High affinity transport of glutamine. Also transport Leu, Ser, Thr, Cys, Met and Asn
Gene Name:
GNP1
Uniprot ID:
P48813
Molecular weight:
73597.39844
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