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MetaCyc Compound: L-alanine

Abbrev Name: ala

Synonyms: alanine, L-α-alanine, ala

Superclasses: an acidall carboxy acidsa carboxylatean amino acida neutral amino acid
an acidall carboxy acidsa carboxylatean amino acida non-polar amino acid
an acidall carboxy acidsa carboxylatean amino acidan alpha amino acida standard alpha amino acid
an acidall carboxy acidsa carboxylatean amino acidan L-amino acid
an amino acid or its derivativean amino acida neutral amino acid
an amino acid or its derivativean amino acida non-polar amino acid
an amino acid or its derivativean amino acidan alpha amino acida standard alpha amino acid
an amino acid or its derivativean amino acidan L-amino acid

Component of: AlaS-L-alanine

Chemical Formula: C3H7NO2

Molecular Weight: 89.094 Daltons

Monoisotopic Molecular Weight: 90.0555035062 Daltons

L-alanine compound structure

SMILES: CC([N+])C([O-])=O

InChI: InChI=1S/C3H7NO2/c1-2(4)3(5)6/h2H,4H2,1H3,(H,5,6)/t2-/m0/s1

InChIKey: InChIKey=QNAYBMKLOCPYGJ-REOHCLBHSA-N

Unification Links: CAS:56-41-7, ChEBI:57972, HMDB:HMDB00161, IAF1260:33629, KEGG:C00041, MetaboLights:MTBLC57972, PubChem:7311724

Standard Gibbs Free Energy of Formation (ΔfG in kcal/mol): -16.772158Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

5-N-acetylardeemin biosynthesis :
anthranilate + L-alanine + L-tryptophan + 3 ATP → ardeemin FQ + 3 AMP + 3 diphosphate + H2O + 2 H+

8-amino-7-oxononanoate biosynthesis I , 8-amino-7-oxononanoate biosynthesis II :
a pimeloyl-[acp] + L-alanine + H+ → 8-amino-7-oxononanoate + CO2 + a holo-[acyl-carrier protein]

8-amino-7-oxononanoate biosynthesis III :
pimeloyl-CoA + L-alanine + H+ → CO2 + 8-amino-7-oxononanoate + coenzyme A

bacilysin biosynthesis :
ATP + L-alanine + L-anticapsin → ADP + bacilysin + phosphate + H+

echinomycin and triostin A biosynthesis :
quinoxaline-2-carboxyl-[acyl-carrier protein] + L-serine + L-alanine + non-ribosomal peptide synthase + 2 ATP → quinoxaline-2-carboxyl-D-seryl-L-alanyl-[non-ribosomal peptide synthase] + a holo-[acyl-carrier protein] + 2 ADP + 2 phosphate + 2 H+

ergotamine biosynthesis :
lysergate + L-alanine + L-phenylalanine + L-proline + an oxidized unknown electron acceptor + H+ → ergotamine + an reduced unknown electron acceptor + 3 H2O

fumiquinazoline D biosynthesis :
fumiquinazoline F-indoline-2',3'-diol + L-alanine + ATP → fumiquinazoline A + AMP + diphosphate + H2O + H+
anthranilate + L-tryptophan + L-alanine + 3 ATP → fumiquinazoline F + 3 AMP + 3 diphosphate + H2O + 2 H+

indole-3-acetyl-amide conjugate biosynthesis :
indole-3-acetate + L-alanine + ATP → indole-3-acetyl-alanine + AMP + diphosphate + H+

methanofuran biosynthesis :
(5-formylfuran-3-yl)methyl phosphate + L-alanine → [5-(aminomethyl)furan-3-yl]methyl phosphate + pyruvate

phosphinothricin tripeptide biosynthesis :
N-acetyl demethylphosphinothricinyl-L-alanyl-[PhsB non-ribosomal peptide synthase] + L-alanine + a PhsC non-ribosomal peptide synthase + ATP → N-acetyl demethylphosphinothricinyl-L-alanyl-L-alanyl-[PhsC non-ribosomal peptide synthase] + AMP + a PhsB non-ribosomal peptide synthase + diphosphate + H+
L-alanine + ATP + H+ → L-alanine adenylate + diphosphate

pyruvate fermentation to opines :
alanopine + NAD+ + H2O ← pyruvate + L-alanine + NADH + H+

saframycin A biosynthesis :
L-alanine + a holo-[SfmA peptidyl-carrier-protein] + H+ → L-alanyl-[SfmA peptidyl-carrier-protein] + H2O

tRNA charging :
a tRNAala + L-alanine + ATP + H+ → an L-alanyl-[tRNAala] + AMP + diphosphate

UDP-N-acetylmuramoyl-pentapeptide biosynthesis I (meso-diaminopimelate containing) , UDP-N-acetylmuramoyl-pentapeptide biosynthesis II (lysine-containing) :
L-alanine + UDP-N-acetyl-α-D-muramate + ATP → UDP-N-acetyl-α-D-muramoyl-L-alanine + ADP + phosphate + H+

zwittermicin A biosynthesis :
a fatty acid + L-asparagine + L-serine + malonyl-CoA + an aminomalonyl-[seryl-carrier protein] + a (2R)-2-hydroxymalonyl-[acp] + β-ureidoalanine + L-alanine + polyketide synthase + 8 NADPH + oxygen + 12 H+ → proto-zwittermicin A-L-alaninyl-[PKS] + 2 CO2 + a holo-[seryl-carrier protein] + a holo-[acyl-carrier protein] + coenzyme A + 8 NADP+ + 9 H2O

γ-glutamyl cycle :
glutathione + a standard α amino acid → an (γ-L-glutamyl)-L-amino acid + L-cysteinyl-glycine

leukotriene biosynthesis :
leukotriene-C4 + a standard α amino acid → an (γ-L-glutamyl)-L-amino acid + leukotriene-D4

Not in pathways:
a standard α amino acid + oxygen + H2O → ammonium + hydrogen peroxide + a 2-oxo carboxylate

4-hydroxy-4-methylglutamate biosynthesis :
4-hydroxy-4-methyl-2-oxoglutarate + an L-amino acid → 4-hydroxy-4-methylglutamate + a 2-oxo carboxylate

prodigiosin biosynthesis :
(S)-3-acetyloctanal + an L-amino acid → 2-methyl-3-n-amyl-dihydropyrrole + a 2-oxo acid + H2O

rhizocticin A and B biosynthesis :
2-keto-5-phosphono-3-cis-pentenoate + an L-amino acidL-2-amino-5-phosphono-3-cis-pentenoate + a 2-oxo carboxylate
2-keto-4-hydroxy-5-phosphonopentanoate + an L-amino acid → 2-amino-4-hydroxy-5-phosphonopentanoate + a 2-oxo carboxylate

3-hydroxy-L-homotyrosine biosynthesis :
4-(4-hydroxyphenyl)-2-oxobutanoate + an amino acidL-homotyrosine + a 2-oxo acid

Reactions known to produce the compound:

3-hydroxy-4-methyl-anthranilate biosynthesis :
3-hydroxy-4-methyl-D-kynurenine + H2O → 3-hydroxy-4-methylanthranilate + L-alanine + H+

indole-3-acetate activation I :
indole-3-acetyl-alanine + H2O → indole-3-acetate + L-alanine

isopropylamine degradation :
L-2-aminopropionaldehyde + NAD(P)+ + H2O → L-alanine + NAD(P)H + 2 H+

L-alanine biosynthesis III , molybdenum cofactor biosynthesis , thiazole biosynthesis I (facultative anaerobic bacteria) , thiazole biosynthesis II (aerobic bacteria) :
an [L-cysteine desulfurase]-L-cysteine + L-cysteine → an [L-cysteine desulfurase] L-cysteine persulfide + L-alanine

L-tryptophan degradation I (via anthranilate) :
L-kynurenine + H2O → L-alanine + anthranilate + H+

L-tryptophan degradation to 2-amino-3-carboxymuconate semialdehyde :
3-hydroxy-L-kynurenine + H2O → 3-hydroxyanthranilate + L-alanine + H+

L-tryptophan degradation XI (mammalian, via kynurenine) :
3-hydroxy-L-kynurenine + H2O → 3-hydroxyanthranilate + L-alanine + H+
L-kynurenine + H2O → L-alanine + anthranilate + H+

lupanine biosynthesis :
3 cadaverine + 4 pyruvate → 17-oxosparteine + 4 L-alanine + H+ + 3 H2O

muropeptide degradation :
L-alanyl-L-glutamate + H2O → L-alanine + L-glutamate

thio-molybdenum cofactor biosynthesis :
L-cysteine + MoO2-molybdopterin cofactor + an reduced unknown electron acceptor → thio-molybdenum cofactor + L-alanine + an oxidized unknown electron acceptor + H2O

[2Fe-2S] iron-sulfur cluster biosynthesis :
L-cystein desulfurase + L-cysteine → an S-sulfanyl-[L-cysteine desulfurase] + L-alanine
a [cysteine desulfurase]-S-sulfanyl-[disordered-form scaffold protein] complex + L-cysteine → an S-sulfanyl-[cysteine desulfurase]-S-sulfanyl-[disordered-form scaffold protein] complex + L-alanine

Not in pathways:
L-alanyl-L-aspartate + H2O → L-alanine + L-aspartate
L-alanyl-L-glutamine + H2O → L-alanine + L-glutamine
L-alanyl-glycine + H2O → L-alanine + glycine
L-alanyl-L-histidine + H2O → L-alanine + L-histidine
L-alanyl-L-leucine + H2O → L-alanine + L-leucine
L-alanyl-L-threonine + H2O → L-alanine + L-threonine
L-methionyl-L-alanine dipeptide + H2O → L-methionine + L-alanine
L-cysteine + an unsulfurated [sulfur carrier] → L-alanine + a sulfurated [sulfur carrier]
a [protein] C-terminal L-alanine + H2O → L-alanine + a [protein] C-terminal amino acid

dimethylsulfoniopropanoate biosynthesis I (Wollastonia) :
S-methyl-L-methionine + a 2-oxo carboxylate + H+ → 3-dimethylsulfoniopropionaldehyde + CO2 + a standard α amino acid

Not in pathways:
amino acids(n) + H2O → a standard α amino acid + amino acids(n-1)
amino acids(n) + H2O → amino acids(n-1) + a standard α amino acid

Reactions known to both consume and produce the compound:

2-aminoethylphosphonate degradation I , 2-aminoethylphosphonate degradation II :
pyruvate + (2-aminoethyl)phosphonate ↔ L-alanine + phosphonoacetaldehyde

4-aminobutanoate degradation IV , L-glutamate degradation IV :
4-aminobutanoate + pyruvate ↔ succinate semialdehyde + L-alanine

anaerobic energy metabolism (invertebrates, cytosol) :
2-oxoglutarate + L-alanine ↔ L-glutamate + pyruvate
L-alanine ↔ D-alanine

β-alanine biosynthesis II , β-alanine degradation II :
3-oxopropanoate + L-alanine ↔ β-alanine + pyruvate

C4 photosynthetic carbon assimilation cycle, NAD-ME type :
2-oxoglutarate + L-alanine ↔ L-glutamate + pyruvate
2-oxoglutarate + L-alanine ↔ L-glutamate + pyruvate

C4 photosynthetic carbon assimilation cycle, PEPCK type :
2-oxoglutarate + L-alanine ↔ L-glutamate + pyruvate
2-oxoglutarate + L-alanine ↔ L-glutamate + pyruvate

γ-coniciene and coniine biosynthesis :
L-alanine + 5-oxooctanal ↔ 8-aminooctan-4-one + pyruvate

glycine biosynthesis III :
glyoxylate + L-alanine ↔ glycine + pyruvate

hypoglycin biosynthesis :
beta-methylenecyclopropyl pyruvate + L-alanine ↔ hypoglycin A + pyruvate

hypotaurine degradation :
pyruvate + hypotaurine ↔ L-alanine + 2-sulfinoacetaldehyde

indole-3-acetate biosynthesis I , indole-3-acetate biosynthesis II :
L-tryptophan + pyruvate ↔ L-alanine + indole-3-pyruvate

L-alanine biosynthesis I :
pyruvate + L-valine ↔ L-alanine + 3-methyl-2-oxobutanoate
L-alanine ↔ D-alanine

L-alanine biosynthesis II , L-alanine degradation II (to D-lactate) , L-alanine degradation III :
2-oxoglutarate + L-alanine ↔ L-glutamate + pyruvate

L-alanine degradation I :
L-alanine ↔ D-alanine

L-alanine degradation IV :
L-alanine + NAD+ + H2O ↔ ammonium + pyruvate + NADH + H+

L-arginine degradation IX (arginine:pyruvate transaminase pathway) :
L-arginine + pyruvate ↔ 5-guanidino-2-oxo-pentanoate + L-alanine

L-histidine degradation V :
L-histidine + pyruvate ↔ imidazole-pyruvate + L-alanine

L-homophenylalanine biosynthesis :
L-phenylalanine + pyruvate ↔ 2-oxo-3-phenylpropanoate + L-alanine
L-homophenylalanine + pyruvate ↔ 2-oxo-4-phenylbutanoate + L-alanine

L-lysine degradation IX :
pyruvate + L-lysine ↔ L-alanine + (S)-2-amino-6-oxohexanoate

L-phenylalanine degradation III :
L-phenylalanine + pyruvate ↔ 2-oxo-3-phenylpropanoate + L-alanine

In Reactions of unknown directionality:

Not in pathways:
L-aspartate + H+ = CO2 + L-alanine
a 2,2-dialkylglycine + pyruvate + H+ = a dialkyl ketone + L-alanine + CO2
aminopentol + pyruvate = (3S,5R,10S,12R,14R,15S,16S)-3,5,10,14,15-pentahydroxy-12,16-dimethylicosan-2-one + L-alanine
N-acetylmuramoyl-L-alaninate + H2O = N-acetylmuramate + L-alanine
a ThiI sulfur-carrier protein + L-cysteine = an S-sulfanyl-[ThiI sulfur-carrier protein] + L-alanine
3-sulfinoalanine + H2O = L-alanine + sulfite + H+
L-selenocysteine + an reduced unknown electron acceptor = L-alanine + selenide + an oxidized unknown electron acceptor + 2 H+
a fatty acid + L-alanine + glycine + a holo-[SfmB peptidyl-carrier-protein] + H+ = an acyl-L-alanyl-glycyl-[SfmB peptidyl-carrier-protein] + 3 H2O
2-amino-4-carboxypyrimidine + L-alanine = lathyrine + CO2 + H2O

Not in pathways:
L-arginine + a standard α amino acid + ATP = a dipeptide with N-terminal L-arginine + ADP + phosphate + H+

Not in pathways:
an L-amino acid = a D-amino acid
an L-amino acid + NAD+ + H2O = a 2-oxo carboxylate + ammonium + NADH + H+
an N-carbamoyl-L-amino acid + H2O + 2 H+ = an L-amino acid + ammonium + CO2
S-ureidoglycine + a 2-oxo carboxylate = oxalurate + an L-amino acid

Not in pathways:
a 5-L-glutamyl-[peptide] + an amino acid = a 5-L-glutamyl-amino acid + a peptide

Not in pathways:
eugenol + a carboxylate + NADP+ = a coniferyl ester + NADPH
a 2-acyl 1-lyso-phosphatidylcholine[periplasm] + H2O[periplasm] = a carboxylate[periplasm] + sn-glycero-3-phosphocholine[periplasm] + H+[periplasm]
an aldehyde + an electron-transfer quinone + H2O = a carboxylate + an electron-transfer quinol + H+
a triacyl-sn-glycerol + H2O = a 1,2-diacyl-sn-glycerol + a carboxylate + H+
a penicillin + H2O = 6-aminopenicillanate + a carboxylate
an aldehyde[periplasm] + FAD[periplasm] + H2O[periplasm] = a carboxylate[periplasm] + FADH2[periplasm]
a nitrile + 2 H2O = a carboxylate + ammonium
an aliphatic nitrile + 2 H2O = a carboxylate + ammonium
an N-acyl-L-homoserine lactone + H2O = L-homoserine lactone + a carboxylate
an aldehyde + an oxidized unknown electron acceptor + H2O = a carboxylate + an reduced unknown electron acceptor + H+

In Transport reactions:
2 L-alanine[out] + 2 H+[out] ↔ 2 L-alanine[in] + 2 H+[in],
Na+[periplasm] + L-alanine[periplasm] → Na+[cytosol] + L-alanine[cytosol],
L-alanine[periplasm] + H+[periplasm]L-alanine[cytosol] + H+[cytosol],
L-alanine[cytosol]L-alanine[periplasm],
a non-polar amino acid[extracellular space] + ATP + H2O ↔ a non-polar amino acid[cytosol] + ADP + phosphate

Enzymes activated by L-alanine, sorted by the type of activation, are:

Activator (Mechanism unknown) of: glutamate dehydrogenase (NAD-dependent) [Bonete96]

Enzymes inhibited by L-alanine, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: glutamine synthetase [Woolfolk67, Bender77, Dahlquist75] Inhibitor (Allosteric) of: pyruvate kinase [Holwerda73] Inhibitor (Mechanism unknown) of: 2-dehydro-3-deoxyphosphoheptonate aldolase, serine acetyltransferase [Hindson03], L-proline:H+ symporter [MacMillan99], 2-amino-4-oxopentanoate thiolase [Jeng74, Comment 1]

This compound has been characterized as an alternative substrate of the following enzymes: ornithine racemase, cysteine aminotransferase, arginine-α-ketoglutarate transaminase, transport of L-leucine, D-alanine transaminase, jasmonyl-isoleucine synthetase, dTDP-3,4-didehydro-2,6-dideoxy-α-D-glucose aminotransferase, aspartate aminotransferase, transport of a dipeptide, strombine synthase


References

Bender77: Bender RA, Janssen KA, Resnick AD, Blumenberg M, Foor F, Magasanik B (1977). "Biochemical parameters of glutamine synthetase from Klebsiella aerogenes." J Bacteriol 129(2);1001-9. PMID: 14104

Bonete96: Bonete MJ, Perez-Pomares F, Ferrer J, Camacho ML (1996). "NAD-glutamate dehydrogenase from Halobacterium halobium: inhibition and activation by TCA intermediates and amino acids." Biochim Biophys Acta 1996;1289(1);14-24. PMID: 8605224

Dahlquist75: Dahlquist FW, Purich DL (1975). "Regulation of Escherichia coli glutamine synthetase. Evidence for the action of some feedback modifiers at the active site of the unadenylylated enzyme." Biochemistry 14(9);1980-9. PMID: 235974

Hindson03: Hindson VJ, Shaw WV (2003). "Random-order ternary complex reaction mechanism of serine acetyltransferase from Escherichia coli." Biochemistry 42(10);3113-9. PMID: 12627979

Holwerda73: Holwerda DA, de Zwaan A (1973). "Kinetic and molecular characteristics of allosteric pyruvate kinase from muscle tissue of the sea mussel Mytilus edulis L." Biochim Biophys Acta 309(2);296-306. PMID: 4354457

Jeng74: Jeng IM, Somack R, Barker HA (1974). "Ornithine degradation in Clostridium sticklandii; pyridoxal phosphate and coenzyme A dependent thiolytic cleavage of 2-amino-4-ketopentanoate to alanine and acetyl coenzyme A." Biochemistry 1974;13(14);2898-903. PMID: 4407783

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

MacMillan99: MacMillan SV, Alexander DA, Culham DE, Kunte HJ, Marshall EV, Rochon D, Wood JM (1999). "The ion coupling and organic substrate specificities of osmoregulatory transporter ProP in Escherichia coli." Biochim Biophys Acta 1420(1-2);30-44. PMID: 10446288

Woolfolk67: Woolfolk CA, Stadtman ER (1967). "Regulation of glutamine synthetase. 3. Cumulative feedback inhibition of glutamine synthetase from Escherichia coli." Arch Biochem Biophys 118(3);736-55. PMID: 4860415


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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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