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L-Proline (YMDB00378)

Identification
YMDB IDYMDB00378
NameL-Proline
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionProline (abbreviated as Pro or P) is an alpha-amino acid or more technically an iminio acid. The L-isomer is one of the 22 proteinogenic amino acids, i.e., the building blocks of proteins. It is classified as a polar amino acid, because of the hydrophilic nature of its cycloalkyl side chain. It is unique among the 20 protein-forming amino acids in that the alpha-amino group is secondary. The distinctive cyclic structure of proline's side chain locks its φ backbone dihedral angle at approximately −75°, giving proline an exceptional conformational rigidity compared to other amino acids. Proline is biosynthetically derived from the amino acid L-glutamate and its immediate precursor is the imino acid (S)-1-pyrroline-5-carboxylate (P5C). Enzymes involved in a typical biosynthesis include: Glutamate kinase; Glutamate dehydrogenase and Pyrroline-5-carboxylate reductase. Proline and its derivatives are often used as asymmetric catalysts in organic reactions. The CBS reduction and proline catalysed aldol condensation are prominent examples. In brewing, proteins rich in proline combine with polyphenols to produce haze (turbidity). Proline is typically the most abundant amino acid found in wine. During fermentation of wine most of the amino acids are practically depleted from the grape juice/ grape must (the juice component including skins, seeds and stems) by the time the first 30 g of sugar have been fermented. Yeast make use of alanine and argnine acids and ammonium (slightly) after the depletion of the other amino acids. Yeast then assimilate arginine only after the disappearance of ammonium from the grape must/juice. Yeasts do not utilize proline during fermentation although it is one of the principle amino acids found in must. During fermentation, yeasts assimilate between 1 and 2 g/L of amino acids. Towards the end of fermentation, yeasts excrete significant but variable amounts of different amino acids. Finally at the end of alcoholic fermentation, a few hundred mg/L of amino acids remain with proline generally represents half.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • (-)-(S)-Proline
  • (-)-2-Pyrrolidinecarboxylate
  • (-)-2-Pyrrolidinecarboxylic acid
  • (-)-Proline
  • (S)-(-)-Proline
  • (S)-(-)-Pyrrolidine-2-carboxylate
  • (S)-(-)-Pyrrolidine-2-carboxylic acid
  • (S)-2-Carboxypyrrolidine
  • (S)-2-Pyrralidinecarboxylate
  • (S)-2-Pyrralidinecarboxylic acid
  • (S)-2-Pyrrolidinecarboxylate
  • (S)-2-Pyrrolidinecarboxylic acid
  • (S)-Proline
  • 2-Pyrrolidinecarboxylate
  • 2-Pyrrolidinecarboxylic acid
  • Proline
  • (2S)-Pyrrolidine-2-carboxylic acid
  • (S)-Pyrrolidine-2-carboxylic acid
  • L-(-)-Proline
  • L-alpha-Pyrrolidinecarboxylic acid
  • L-Prolin
  • L-Pyrrolidine-2-carboxylic acid
  • P
  • Prolina
  • Prolinum
  • (2S)-Pyrrolidine-2-carboxylate
  • (S)-Pyrrolidine-2-carboxylate
  • L-a-Pyrrolidinecarboxylate
  • L-a-Pyrrolidinecarboxylic acid
  • L-alpha-Pyrrolidinecarboxylate
  • L-Α-pyrrolidinecarboxylate
  • L-Α-pyrrolidinecarboxylic acid
  • L-Pyrrolidine-2-carboxylate
  • L Proline
CAS number147-85-3
WeightAverage: 115.1305
Monoisotopic: 115.063328537
InChI KeyONIBWKKTOPOVIA-BYPYZUCNSA-N
InChIInChI=1S/C5H9NO2/c7-5(8)4-2-1-3-6-4/h4,6H,1-3H2,(H,7,8)/t4-/m0/s1
IUPAC Name(2S)-pyrrolidine-2-carboxylic acid
Traditional IUPAC NameL-proline
Chemical FormulaC5H9NO2
SMILES[H]OC(=O)[C@@]1([H])N([H])C([H])([H])C([H])([H])C1([H])[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as proline and derivatives. Proline and derivatives are compounds containing proline or a derivative thereof resulting from reaction of proline 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 ParentProline and derivatives
Alternative Parents
Substituents
  • Proline or derivatives
  • Alpha-amino acid
  • L-alpha-amino acid
  • Pyrrolidine carboxylic acid
  • Pyrrolidine carboxylic acid or derivatives
  • Pyrrolidine
  • Amino acid
  • Carboxylic acid
  • Secondary aliphatic amine
  • Monocarboxylic acid or derivatives
  • Secondary amine
  • Organoheterocyclic compound
  • Azacycle
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Organopnictogen compound
  • Organic oxide
  • Carbonyl group
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting point221 °C
Experimental Properties
PropertyValueReference
Water Solubility162 mg/mL at 25 oC [MERCK INDEX (1996)]PhysProp
LogP-2.54 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility365 g/LALOGPS
logP-2.7ALOGPS
logP-2.6ChemAxon
logS0.5ALOGPS
pKa (Strongest Acidic)1.94ChemAxon
pKa (Strongest Basic)11.33ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.33 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity28.06 m³·mol⁻¹ChemAxon
Polarizability11.5 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • extracellular
  • mitochondrion
  • cytoplasm
Organoleptic Properties
Flavour/OdourSource
OdorlessFDB000570
SMPDB Pathways
Proline MetabolismPW002365 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Arginine and proline metabolismec00330 Map00330
SMPDB Reactions
1-Pyrroline-5-carboxylic acid + hydron + NADPH → NADP + L-Proline
L-Proline + Ubiquinone Q1 → hydron + QH(2) + 1-Pyrroline-5-carboxylic acid
KEGG Reactions
L-Proline + NAD → NADH + 1-Pyrroline-5-carboxylic acid + hydron
L-Proline + Adenosine triphosphate + tRNA(Pro) → Adenosine monophosphate + Pyrophosphate + Pro-tRNA(Pro) + hydron
1-Pyrroline-5-carboxylic acid + NADPH + hydron → NADP + L-Proline
Concentrations
Intracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
1075 ± 54 µM YEB media with 0.5 mM glucoseaerobicBaker's yeastExperimentally Determined
Not Available
Conversion Details Here
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-0006-0910000000-a9127c0e370afb80259bJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-000f-0910000000-3195f21e625520d51316JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0006-0900000000-119af746c347969e8ae7JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-006x-8900000000-b31beabb1ed6235e7145JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-00di-9100000000-c1c67bc521741ee891cbJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0006-1900000000-84e6fb318323fd0261b1JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-00xs-8910000000-74b0c34ca5fd7c85f1d9JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00fu-9000000000-716c3d01b301162863b6JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-0900000000-0d7354201ed866c87b13JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0006-0910000000-a9127c0e370afb80259bJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000f-0910000000-3195f21e625520d51316JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0006-0900000000-119af746c347969e8ae7JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-QQ (Non-derivatized)splash10-001i-1920000000-09006ee4e7a137d8a45aJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-006x-8900000000-b31beabb1ed6235e7145JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0006-1900000000-84e6fb318323fd0261b1JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00xs-8910000000-74b0c34ca5fd7c85f1d9JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00di-9100000000-c1c67bc521741ee891cbJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00fu-9000000000-d203e3dfb0701403a75bJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9000000000-56471980a375d26046caJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-03di-0900000000-2c23774af5f6a0c217d5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-03di-0900000000-d89c1e626ef24a79c89fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-03di-1900000000-fc27094f2eb75e65b438JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-03di-0900000000-e1d0a4b20419dc7bae92JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03di-0900000000-2c23774af5f6a0c217d5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03di-0900000000-d89c1e626ef24a79c89fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03di-1900000000-fc27094f2eb75e65b438JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-03di-0900000000-e1d0a4b20419dc7bae92JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00xr-9600000000-ba51a901e786b1a4663eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-9000000000-f72e2f3812225708fc56JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00di-9000000000-59887da6580f63bcc1c5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-00fu-9000000000-c69dcaf7cb2d1e9d285eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014i-0930000000-984f9a23ebfe28f95017JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014i-9000000000-f75575cac28a54aa923dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00di-9000000000-221cfb8c82f3df76eb51JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014i-0900000000-e5741fd9870218d57cafJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014i-0900000000-6bc9b4e775be37fa18d9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014i-9000000000-a8eb419b26655a6a1dabJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00di-9000000000-873ee03b61d1ffcae70fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014i-0900000000-61d583960651669fb9e6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-014i-1900000000-3221c23504b8847abf8dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-00di-9100000000-8169367f5127c57fae12JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-00di-9000000000-f704eb8402fcacfccd18JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-00di-9000000000-ccd74eea36efab2cbab8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-00di-9000000000-9f214692cd39a6581813JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • 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
  • 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
Synthesis Reference: Itoh, Tamio. Synthesis of L-proline from L-glutamine. Bulletin of the Chemical Society of Japan (1963), 36(1), 25-9
External Links:
ResourceLink
CHEBI ID17203
HMDB IDHMDB00162
Pubchem Compound ID145742
Kegg IDC00148
ChemSpider ID128566
FOODB IDFDB000570
WikipediaProline
BioCyc IDPRO

Enzymes

Protein Details
1. Probable prolyl-tRNA synthetase, mitochondrial
General function:
Involved in nucleotide binding
Specific function:
ATP + L-proline + tRNA(Pro) = AMP + diphosphate + L-prolyl-tRNA(Pro)
Gene Name:
AIM10
Uniprot ID:
P39965
Molecular weight:
65879.70313
Reactions
ATP + L-proline + tRNA(Pro) → AMP + diphosphate + L-prolyl-tRNA(Pro).
Protein Details
2. Putative prolyl-tRNA synthetase YHR020W
General function:
Involved in nucleotide binding
Specific function:
ATP + L-proline + tRNA(Pro) = AMP + diphosphate + L-prolyl-tRNA(Pro)
Gene Name:
Not Available
Uniprot ID:
P38708
Molecular weight:
77385.70313
Reactions
ATP + L-proline + tRNA(Pro) → AMP + diphosphate + L-prolyl-tRNA(Pro).
Protein Details
3. Proline dehydrogenase, mitochondrial
General function:
Involved in proline dehydrogenase activity
Specific function:
Converts proline to delta-1-pyrroline-5-carboxylate
Gene Name:
PUT1
Uniprot ID:
P09368
Molecular weight:
53270.89844
Reactions
L-proline + acceptor → (S)-1-pyrroline-5-carboxylate + reduced acceptor.
Protein Details
4. Pyrroline-5-carboxylate reductase
General function:
Involved in oxidoreductase activity
Specific function:
L-proline + NAD(P)(+) = 1-pyrroline-5- carboxylate + NAD(P)H
Gene Name:
PRO3
Uniprot ID:
P32263
Molecular weight:
30131.59961
Reactions
L-proline + NAD(P)(+) → 1-pyrroline-5-carboxylate + NAD(P)H.

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. Proline-specific permease
General function:
Involved in transport
Specific function:
Required for high-affinity proline transport. May be responsible for proline recognition and probably also for proline translocation across the plasma membrane. Also function as non- specific GABA permease. Can also transport alanine and glycine
Gene Name:
PUT4
Uniprot ID:
P15380
Molecular weight:
68786.79688