L-Proline (YMDB00378)

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Identification

YMDB ID

YMDB00378

Name

L-Proline

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

Proline (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

MOL SDF PDB SMILES InChI

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 number

147-85-3

Weight

Average: 115.1305
Monoisotopic: 115.063328537

InChI Key

ONIBWKKTOPOVIA-BYPYZUCNSA-N

InChI

InChI=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 Name

L-proline

Chemical Formula

C₅H₉NO₂

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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Proline 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 Framework

Aliphatic heteromonocyclic compounds

External Descriptors

proteinogenic amino acid (CHEBI:17203 )
L-alpha-amino acid (CHEBI:17203 )
proline (CHEBI:17203 )
glutamine family amino acid (CHEBI:17203 )
Common amino acids (C00148 )

Physical Properties

State

Solid

Charge

Melting point

221 °C

Experimental Properties

Property	Value	Reference
Water Solubility	162 mg/mL at 25 oC [MERCK INDEX (1996)]	PhysProp
LogP	-2.54 [HANSCH,C ET AL. (1995)]	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	365 g/L	ALOGPS
logP	-2.7	ALOGPS
logP	-2.6	ChemAxon
logS	0.5	ALOGPS
pKa (Strongest Acidic)	1.94	ChemAxon
pKa (Strongest Basic)	11.33	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.33 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	28.06 m³·mol⁻¹	ChemAxon
Polarizability	11.5 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
Odorless	FDB000570

SMPDB Pathways

Proline Metabolism

PW002365

KEGG Pathways

Arginine and proline metabolism

ec00330

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 Concentration	Substrate	Growth Conditions	Strain	Citation
1075 ± 54 µM	YEB media with 0.5 mM glucose	aerobic	Baker's yeast	Experimentally Determined Not Available
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)	splash10-0006-0910000000-a9127c0e370afb80259b	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-000f-0910000000-3195f21e625520d51316	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0006-0900000000-119af746c347969e8ae7	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-006x-8900000000-b31beabb1ed6235e7145	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-00di-9100000000-c1c67bc521741ee891cb	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-0006-1900000000-84e6fb318323fd0261b1	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-00xs-8910000000-74b0c34ca5fd7c85f1d9	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00fu-9000000000-716c3d01b301162863b6	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-0900000000-0d7354201ed866c87b13	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0006-0910000000-a9127c0e370afb80259b	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-000f-0910000000-3195f21e625520d51316	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0006-0900000000-119af746c347969e8ae7	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-QQ (Non-derivatized)	splash10-001i-1920000000-09006ee4e7a137d8a45a	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-006x-8900000000-b31beabb1ed6235e7145	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0006-1900000000-84e6fb318323fd0261b1	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00xs-8910000000-74b0c34ca5fd7c85f1d9	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00di-9100000000-c1c67bc521741ee891cb	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00fu-9000000000-d203e3dfb0701403a75b	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9000000000-56471980a375d26046ca	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00xr-9600000000-ba51a901e786b1a4663e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00di-9000000000-f72e2f3812225708fc56	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-00di-9000000000-59887da6580f63bcc1c5	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive	splash10-00fu-9000000000-c69dcaf7cb2d1e9d285e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-014i-0930000000-984f9a23ebfe28f95017	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-014i-9000000000-f75575cac28a54aa923d	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-00di-9000000000-221cfb8c82f3df76eb51	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-014i-0900000000-e5741fd9870218d57caf	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-014i-0900000000-6bc9b4e775be37fa18d9	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-014i-9000000000-a8eb419b26655a6a1dab	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-00di-9000000000-873ee03b61d1ffcae70f	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-014i-0900000000-61d583960651669fb9e6	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-03di-0900000000-2c23774af5f6a0c217d5	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-03di-0900000000-d89c1e626ef24a79c89f	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-03di-1900000000-fc27094f2eb75e65b438	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-014i-1900000000-3221c23504b8847abf8d	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-00di-9100000000-8169367f5127c57fae12	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-00di-9000000000-f704eb8402fcacfccd18	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-00di-9000000000-ccd74eea36efab2cbab8	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-00di-9000000000-9f214692cd39a6581813	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - CE-ESI-TOF (CE-system connected to 6210 Time-of-Flight MS, Agilent) , Positive	splash10-014i-0900000000-ef038c77922e4c89eeb0	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-00di-9400000000-4073ea1df57a60b36d69	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive	splash10-00di-9000000000-495fdbd2f565bd794632	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-03di-0900000000-e1d0a4b20419dc7bae92	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-6900000000-eba8ceb2a71d2726acd0	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	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:

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:

Resource	Link
CHEBI ID	17203
HMDB ID	HMDB00162
Pubchem Compound ID	145742
Kegg ID	C00148
ChemSpider ID	128566
FOODB ID	FDB000570
Wikipedia	Proline
BioCyc ID	PRO

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

Structure for #<Compound:0xab6226e4>

Enzymes

Reactions

Reactions

Reactions

Reactions

Transporters