Record Information
Version2.0
Creation Date2012-05-31 13:49:38 -0600
Update Date2015-09-13 12:56:10 -0600
Secondary Accession Numbers
  • ECMDB01310
Identification
Name:D-Alanine
Description:D-Alanine is an amino acid and one of the most important molecules in living organisms. It has a chiral carbon at a -position.
Structure
Thumb
Synonyms:
  • (R)-Alanine
  • D(-)-a -Alanine
  • D(-)-a-Alanine
  • D(-)-alpha-Alanine
  • D(-)-α-Alanine
  • D-(-)-Alanine
  • D-2-Aminopropionate
  • D-2-Aminopropionic acid
  • D-a-Alanine
  • D-Ala
  • D-Alanine
  • D-alpha-Alanine
  • D-α-Alanine
  • Delta-(-)-Alanine
  • Delta-2-Aminopropionate
  • Delta-2-Aminopropionic acid
  • delta-a-Alanine
  • Delta-Alanine
  • Delta-alpha-Alanine
  • Dl-Alanine
  • δ-(-)-Alanine
  • δ-2-Aminopropionate
  • δ-2-Aminopropionic acid
  • δ-a-Alanine
  • δ-Alanine
  • δ-α-Alanine
Chemical Formula:C3H7NO2
Weight:Average: 89.0932
Monoisotopic: 89.047678473
InChI Key:QNAYBMKLOCPYGJ-UWTATZPHSA-N
InChI:InChI=1S/C3H7NO2/c1-2(4)3(5)6/h2H,4H2,1H3,(H,5,6)/t2-/m1/s1
CAS number:338-69-2
IUPAC Name:(2R)-2-aminopropanoic acid
Traditional IUPAC Name:D-alanine
SMILES:C[C@@H](N)C(O)=O
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as alanine and derivatives. These are compounds containing alanine or a derivative thereof resulting from reaction of alanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct ParentAlanine and derivatives
Alternative Parents
Substituents
  • Alanine or derivatives
  • Alpha-amino acid
  • D-alpha-amino acid
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Organopnictogen compound
  • Organic oxide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:0
Melting point:292 °C
Experimental Properties:
PropertyValueSource
Water Solubility:165.0 mg/ml [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogP:-2.912PhysProp
Predicted Properties
PropertyValueSource
Water Solubility447.0 mg/mLALOGPS
logP-3ALOGPS
logP-2.8ChemAxon
logS0.7ALOGPS
pKa (Strongest Acidic)2.47ChemAxon
pKa (Strongest Basic)9.48ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity20.5 m3·mol-1ChemAxon
Polarizability8.54 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
two linked disacharide pentapeptide murein units (uncrosslinked, middle of chain) > D-Alanine + two disacharide linked murein units, pentapeptide crosslinked tetrapeptide (A2pm->D-ala) (middle of chain)
three linked disacharide pentapeptide murein units (uncrosslinked, middle of chain) >2 D-Alanine + three disacharide linked murein units (pentapeptide crosslinked tetrapeptide (A2pm->D-ala) tetrapeptide corsslinked tetrapeptide (A2pm->D-ala)) (middle of chain)
2 D-Alanine + Adenosine triphosphate <> ADP + D-Alanyl-D-alanine + Hydrogen ion + Phosphate
Water + three disacharide linked murein units (pentapeptide crosslinked tetrapeptide (A2pm->D-ala) tetrapeptide corsslinked tetrapeptide (A2pm->D-ala)) (middle of chain) > D-Alanine + three disacharide linked murein units (tetrapeptide crosslinked tetrapeptide (A2pm->D-ala) & tetrapeptide corsslinked tetrapeptide (A2pm->D-ala)) (middle of chain)
Water + two disacharide linked murein units, pentapeptide crosslinked tetrapeptide (A2pm->D-ala) (middle of chain) > D-Alanine + two disacharide linked murein units, tetrapeptide corsslinked tetrapeptide (A2pm->D-ala) (middle of chain)
Water + two linked disacharide pentapeptide and tetrapeptide murein units (uncrosslinked, middle of chain) > D-Alanine + two linked disacharide tetrapeptide murein units (uncrosslinked, middle of chain)
Water + two linked disacharide pentapeptide and tripeptide murein units (uncrosslinked, middle of chain) > D-Alanine + two linked disacharide tetrapeptide and tripeptide murein units (uncrosslinked, middle of chain)
Water + two linked disacharide pentapeptide murein units (uncrosslinked, middle of chain) > D-Alanine + two linked disacharide pentapeptide and tetrapeptide murein units (uncrosslinked, middle of chain)
L-Alanine <> D-Alanine
D-Alanine + Pyridoxal 5'-phosphate > Pyridoxamine 5'-phosphate + Pyruvic acid
D-Alanine + FAD + Water > FADH2 + Ammonium + Pyruvic acid
Water + UDP-N-acetylmuramoyl-L-alanyl-D-gamma-glutamyl-meso-2,6-diaminopimelate-D-alanine > D-Alanine + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioate
1,6-Anhydrous-N-Acetylmuramyl-tetrapeptide + Water > D-Alanine + 1,6-Anhydrous-N-Acetylmuramyl-tripeptide
L-Alanine-D-glutamate-meso-2,6-diaminoheptanedioate-D-alanine + Water > L-alanine-D-glutamate-meso-2,6-diaminoheptanedioate + D-Alanine
N-Acetyl-D-glucosamine(anhydrous)N-Acetylmuramyl-tetrapeptide + Water > D-Alanine + N-Acetyl-D-glucosamine(anhydrous)N-Acetylmuramyl-tripeptide
D-Alanyl-D-alanine + Water >2 D-Alanine
L-Alanine <> D-Alanine
Adenosine triphosphate + 2 D-Alanine <> ADP + Phosphate + D-Alanyl-D-alanine
D-Alanine + Pyridoxal 5'-phosphate <> Pyruvic acid + Pyridoxamine 5'-phosphate
peptidoglycan tetrapeptide, glycan chain 2 + peptidoglycan tetrapeptide, glycan chain 1 > peptidoglycan DAP-DAP crosslink + D-Alanine
D-Alanyl-D-alanine + Water > D-Alanine
a lipid II + Water a <i>N</i>-acetylglucosamine--<i>N</i>-acetylmuramyl-(tetrapeptide) pyrophosphoryl-undecaprenol + D-Alanine
L-Alanine <> D-Alanine
D-Alanine + Adenosine triphosphate > Hydrogen ion + D-Alanyl-D-alanine + Phosphate + ADP
an electron-transfer-related quinone + Water + D-Alanine > an electron-transfer-related quinol + Ammonium + Pyruvic acid

SMPDB Pathways:
D-Alanine metabolismPW000768 Pw000768Pw000768 greyscalePw000768 simple
L-alanine metabolismPW000788 Pw000788Pw000788 greyscalePw000788 simple
inner membrane transportPW000786 Pw000786Pw000786 greyscalePw000786 simple
peptidoglycan biosynthesis IPW000906 Pw000906Pw000906 greyscalePw000906 simple
peptidoglycan biosynthesis I 2PW002062 Pw002062Pw002062 greyscalePw002062 simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0006-9000000000-597f42bcde0e9f005b7eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-9000000000-ffef20b2a24280b6fac1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0007-9000000000-5494d4107e065019362aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-000i-9000000000-536fa384ea61b8df326eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-000i-9000000000-447340852e905814000eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0006-9000000000-320cdf459ab1249aeeadView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0006-9000000000-e42a8e9c2a1c69fb6bb2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0006-9000000000-2c2b7ae491c5edb0c9caView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0006-9000000000-4832fe79b009c4a4841eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0006-9000000000-b70e34a4340b1eba96fbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • D'Aniello A, Vetere A, Fisher GH, Cusano G, Chavez M, Petrucelli L: Presence of D-alanine in proteins of normal and Alzheimer human brain. Brain Res. 1992 Oct 2;592(1-2):44-8. Pubmed: 1450921
  • Fisher GH, D'Aniello A, Vetere A, Padula L, Cusano GP, Man EH: Free D-aspartate and D-alanine in normal and Alzheimer brain. Brain Res Bull. 1991 Jun;26(6):983-5. Pubmed: 1933416
  • Fukushima T, Santa T, Homma H, Nagatomo R, Imai K: Determination of D-amino acids in serum from patients with renal dysfunction. Biol Pharm Bull. 1995 Aug;18(8):1130-2. Pubmed: 8535409
  • Hamase K, Konno R, Morikawa A, Zaitsu K: Sensitive determination of D-amino acids in mammals and the effect of D-amino-acid oxidase activity on their amounts. Biol Pharm Bull. 2005 Sep;28(9):1578-84. Pubmed: 16141519
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Nagata Y, Masui R, Akino T: The presence of free D-serine, D-alanine and D-proline in human plasma. Experientia. 1992 Oct 15;48(10):986-8. Pubmed: 1426150
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID15570
HMDB IDHMDB01310
Pubchem Compound ID71080
Kegg IDC00133
ChemSpider ID64234
WikipediaD-Alanine
BioCyc IDD-ALANINE
EcoCyc IDD-ALANINE
Ligand ExpoDAL

Enzymes

General function:
Involved in catalytic activity
Specific function:
Cell wall formation. Synthesis of cross-linked peptidoglycan from the lipid intermediates. The enzyme has a penicillin-insensitive transglycosylase N-terminal domain (formation of linear glycan strands) and a penicillin-sensitive transpeptidase C-terminal domain (cross-linking of the peptide subunits)
Gene Name:
mrcA
Uniprot ID:
P02918
Molecular weight:
93636
General function:
Involved in catalytic activity
Specific function:
Cell wall formation. Synthesis of cross-linked peptidoglycan from the lipid intermediates. The enzyme has a penicillin-insensitive transglycosylase N-terminal domain (formation of linear glycan strands) and a penicillin-sensitive transpeptidase C-terminal domain (cross-linking of the peptide subunits)
Gene Name:
mrcB
Uniprot ID:
P02919
Molecular weight:
94292
Reactions
(GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala))(n)-diphosphoundecaprenol + GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol = (GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala))(n+1)-diphosphoundecaprenol + undecaprenyl diphosphate.
General function:
Involved in ATP binding
Specific function:
Cell wall formation
Gene Name:
ddlB
Uniprot ID:
P07862
Molecular weight:
32839
Reactions
ATP + 2 D-alanine = ADP + phosphate + D-alanyl-D-alanine.
General function:
Involved in alanine racemase activity
Specific function:
Provides the D-alanine required for cell wall biosynthesis
Gene Name:
alr
Uniprot ID:
P0A6B4
Molecular weight:
39153
Reactions
L-alanine = D-alanine.
General function:
Involved in D-amino-acid dehydrogenase activity
Specific function:
Oxidative deamination of D-amino acids
Gene Name:
dadA
Uniprot ID:
P0A6J5
Molecular weight:
47607
Reactions
A D-amino acid + H(2)O + acceptor = a 2-oxo acid + NH(3) + reduced acceptor.
General function:
Involved in ATP binding
Specific function:
Cell wall formation
Gene Name:
ddlA
Uniprot ID:
P0A6J8
Molecular weight:
39315
Reactions
ATP + 2 D-alanine = ADP + phosphate + D-alanyl-D-alanine.
General function:
Involved in catalytic activity
Specific function:
Interconversion of serine and glycine
Gene Name:
glyA
Uniprot ID:
P0A825
Molecular weight:
45316
Reactions
5,10-methylenetetrahydrofolate + glycine + H(2)O = tetrahydrofolate + L-serine.
General function:
Involved in penicillin binding
Specific function:
Cell wall formation. Essential for the formation of a septum of the murein sacculus. Synthesis of cross-linked peptidoglycan from the lipid intermediates
Gene Name:
ftsI
Uniprot ID:
P0AD68
Molecular weight:
63877
Reactions
(GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala))(n)-diphosphoundecaprenol + GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol = (GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala))(n+1)-diphosphoundecaprenol + undecaprenyl diphosphate.
General function:
Involved in alanine racemase activity
Specific function:
Isomerizes L-alanine to D-alanine which is then oxidized to pyruvate by dadA
Gene Name:
dadX
Uniprot ID:
P29012
Molecular weight:
38844
Reactions
L-alanine = D-alanine.
General function:
Involved in lyase activity
Specific function:
Catalyzes the cleavage of L-allo-threonine and L- threonine to glycine and acetaldehyde. L-threo-phenylserine and L- erythro-phenylserine are also good substrates
Gene Name:
ltaE
Uniprot ID:
P75823
Molecular weight:
36494
Reactions
L-threonine = glycine + acetaldehyde.
L-allo-threonine = glycine + acetaldehyde.
General function:
Defense mechanisms
Specific function:
Releases the terminal D-alanine residue from the cytoplasmic tetrapeptide recycling product L-Ala-gamma-D-Glu-meso- Dap-D-Ala. To a lesser extent, can also cleave D-Ala from murein derivatives containing the tetrapeptide, i.e. MurNAc-tetrapeptide, UDP-MurNAc-tetrapeptide, GlcNAc-MurNAc-tetrapeptide, and GlcNAc- anhMurNAc-tetrapeptide. Does not act on murein sacculi or cross- linked muropeptides. The tripeptides produced by the lcdA reaction can then be reused as peptidoglycan building blocks; lcdA is thereby involved in murein recycling. Is also essential for viability during stationary phase
Gene Name:
ldcA
Uniprot ID:
P76008
Molecular weight:
33567
Reactions
GlcNAc-MurNAc-L-alanyl-gamma-D-glutamyl-meso-diaminopimelyl-D-alanine + H(2)O = GlcNAc-MurNAc-L-alanyl-gamma-D-glutamyl-meso-diaminopimelate + D-alanine.
General function:
Involved in carboxypeptidase activity
Specific function:
Removes C-terminal D-alanyl residues from sugar-peptide cell wall precursors
Gene Name:
dacC
Uniprot ID:
P08506
Molecular weight:
43609
Reactions
Preferential cleavage: (Ac)(2)-L-Lys-D-Ala-|-D-Ala. Also transpeptidation of peptidyl-alanyl moieties that are N-acyl substituents of D-alanine.
General function:
Involved in carboxypeptidase activity
Specific function:
Removes C-terminal D-alanyl residues from sugar-peptide cell wall precursors
Gene Name:
dacD
Uniprot ID:
P33013
Molecular weight:
43346
Reactions
Preferential cleavage: (Ac)(2)-L-Lys-D-Ala-|-D-Ala. Also transpeptidation of peptidyl-alanyl moieties that are N-acyl substituents of D-alanine.
General function:
Involved in penicillin binding
Specific function:
Cell wall formation; PBP-2 is responsible for the determination of the rod shape of the cell. Its synthesize cross- linked peptidoglycan from the lipid intermediates
Gene Name:
mrdA
Uniprot ID:
P0AD65
Molecular weight:
70856
General function:
Involved in carboxypeptidase activity
Specific function:
Removes C-terminal D-alanyl residues from sugar-peptide cell wall precursors
Gene Name:
dacA
Uniprot ID:
P0AEB2
Molecular weight:
44444
Reactions
Preferential cleavage: (Ac)(2)-L-Lys-D-Ala-|-D-Ala. Also transpeptidation of peptidyl-alanyl moieties that are N-acyl substituents of D-alanine.
A beta-lactam + H(2)O = a substituted beta-amino acid.
General function:
Involved in metallopeptidase activity
Specific function:
Hydrolyzes D-Ala-D-Ala. May have a role in cell-wall turnover
Gene Name:
ddpX
Uniprot ID:
P77790
Molecular weight:
21213
Reactions
D-Ala-D-Ala + H(2)O = 2 D-Ala.
General function:
Involved in serine-type carboxypeptidase activity
Specific function:
Not involved in transpeptidation but exclusively catalyzes a DD-carboxypeptidase and DD-endopeptidase reaction
Gene Name:
dacB
Uniprot ID:
P24228
Molecular weight:
51798
Reactions
Preferential cleavage: (Ac)(2)-L-Lys-D-Ala-|-D-Ala. Also transpeptidation of peptidyl-alanyl moieties that are N-acyl substituents of D-alanine.

Transporters

General function:
Involved in nucleotide binding
Specific function:
Probably part of a binding-protein-dependent transport system yecCS for an amino acid. Probably responsible for energy coupling to the transport system
Gene Name:
yecC
Uniprot ID:
P37774
Molecular weight:
27677
General function:
Involved in transporter activity
Specific function:
Probably part of the binding-protein-dependent transport system yecCS for an amino acid; probably responsible for the translocation of the substrate across the membrane
Gene Name:
yecS
Uniprot ID:
P0AFT2
Molecular weight:
24801
General function:
Involved in transport
Specific function:
Permease that is involved in the transport across the cytoplasmic membrane of D-alanine, D-serine and glycine
Gene Name:
cycA
Uniprot ID:
P0AAE0
Molecular weight:
51659
General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
General function:
Involved in transporter activity
Specific function:
Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:
phoE
Uniprot ID:
P02932
Molecular weight:
38922
General function:
Involved in transporter activity
Specific function:
OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:
ompF
Uniprot ID:
P02931
Molecular weight:
39333
General function:
Involved in transporter activity
Specific function:
Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:
ompC
Uniprot ID:
P06996
Molecular weight:
40368