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Alanine

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Alanine
Names
L-Alanine
IUPAC name Alanine
Other names 2-Aminopropanoic acid
Identifiers
CAS Number	338-69-2(D-isomer)^Y 56-41-7(L-isomer)^Y 302-72-7(racemic)^Y
3D model (JSmol)	Interactive image Zwitterion:Interactive image Interactive image Zwitterion:Interactive image
ChEBI	CHEBI:16977^N
ChEMBL	ChEMBL66693^Y
ChemSpider	64234(D-isomer)^Y 5735(L-isomer)^Y 582(Racemic)^Y
ECHA InfoCard	100.000.249
EC Number	206-126-4
IUPHAR/BPS	720
KEGG	C01401^N
PubChem CID	5950
UNII	1FU7983T0U^N
CompTox Dashboard(EPA)	DTXSID20873899

SMILES O=C(O)C(N)C Zwitterion:O=C([O-])C([NH3+])C O=C(O)[C@@H](N)C Zwitterion:O=C([O-])[C@@H]([NH3+])C
Properties
Chemical formula	C₃H₇NO₂
Molar mass	89.09 g·mol⁻¹
Appearance	white powder
Density	1.424 g/cm³
Melting point	258 °C (496 °F; 531 K)(sublimes)
Solubility in water	167.2 g/L (25 °C)
logP	-0.68^[1]
Acidity (pK_a)	2.34 (carboxyl; H₂O) 9.87 (amino; H₂O)^[2]
Magnetic susceptibility (χ)	-50.5·10⁻⁶ cm³/mol
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
N verify (what is ^YN ?)
Infobox references

Alanine (abbreviated asAla orA)^[3] is an α-amino acid. It has thechemical formula CH₃CH(NH₂)COOH.

TheL-isomer is one of the 20amino acids encoded by thegenetic code. Its codons are GCU, GCC, GCA, and GCG. It is classified as anon-polar amino acid.^[4]

L-Alanine accounts for 7.8% of theprimary structure in a sample of 1,150proteins.^[5]^[6]Leucine is the only amino acid which is more common.

D-Alanine occurs inbacterial cell walls and in somepeptide antibiotics.

References

[change |change source]

↑"L-alanine_msds".
↑Haynes, William M., ed. (2016).CRC Handbook of Chemistry and Physics (97th ed.).CRC Press. p. 5–88.ISBN 978-1498754286.
↑Nomenclature and symbolism for amino acids and peptides. IUPAC-IUB Recommendations 1983.Pure Appl. Chem.56 (5), 1984: 595–624.
↑Non-polar: electrons shared so that there is no difference in electric charge between different parts of the molecule.
↑Doolittle, R. F. (1989), "Redundancies in protein sequences", in Fasman, G. D. (ed.),Prediction of protein structures and the principles of protein conformation, New York: Plenum, pp. 599–623,ISBN 0-306-43131-9
↑Primary structure: the exact specification of its atomic structure and its chemical bonds.

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Encoded (proteinogenic) amino acids

General topics

By properties

Aliphatic	Alanine Branched-chain amino acids (Valine Isoleucine Leucine) Methionine Proline Glycine
Aromatic	Phenylalanine Tyrosine Tryptophan Histidine
Polar, uncharged	Asparagine Threonine Glutamine Serine
Positive charge (pK_a)	Histidine (≈6.1) Lysine (≈10.8) Arginine (≈12.5) Pyrrolysine
Negative charge (pK_a)	Aspartic acid (≈3.9) Glutamic acid (≈4.1) Selenocysteine (≈5.4) Cysteine (≈8.3) Tyrosine (≈10.1)

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Neurotransmitters

Amino acid-derived

Major excitatory /
inhibitory systems

Glutamate system	Agmatine Aspartic acid (aspartate) Glutamic acid (glutamate) Glutathione Glycine GSNO GSSG Kynurenic acid NAA NAAG Proline Serine
GABA system	GABA GABOB GHB
Glycine system	α-Alanine β-Alanine Glycine Hypotaurine Proline Sarcosine Serine Taurine
GHB system	GHB T-HCA (GHC)

Biogenic amines

Monoamines	6-OHM Dopamine Epinephrine (adrenaline) NAS (normelatonin) Norepinephrine (noradrenaline) Serotonin (5-HT)
Trace amines	3-Iodothyronamine N-Methylphenethylamine N-Methyltryptamine m-Octopamine p-Octopamine Phenylethanolamine Phenethylamine Synephrine Tryptamine m-Tyramine p-Tyramine
Others	Histamine

Seehere instead.

Lipid-derived

Endocannabinoids

Seehere instead.

Nucleobase-derived

Nucleosides

Adenosine system	ADP AMP ATP

Vitamin-derived

Cholinergic system	Acetylcholine

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Amino acid metabolism metabolic intermediates

lysine→	Saccharopine Allysine α-Aminoadipic acid 2-Oxoadipic acid Glutaryl-CoA Glutaconyl-CoA Crotonyl-CoA β-Hydroxybutyryl-CoA
leucine→	β-Hydroxy β-methylbutyric acid β-Hydroxy β-methylbutyryl-CoA Isovaleryl-CoA α-Ketoisocaproic acid β-Ketoisocaproic acid β-Ketoisocaproyl-CoA β-Leucine β-Methylcrotonyl-CoA β-Methylglutaconyl-CoA β-Hydroxy β-methylglutaryl-CoA
tryptophan→alanine→	N′-Formylkynurenine Kynurenine Anthranilic acid 3-Hydroxykynurenine 3-Hydroxyanthranilic acid 2-Amino-3-carboxymuconic semialdehyde 2-Aminomuconic semialdehyde 2-Aminomuconic acid Glutaryl-CoA

G→pyruvate→
citrate

glycine→ serine→	3-Phosphoglyceric acid glycine→creatine:Glycocyamine Phosphocreatine Creatinine

G→glutamate→
α-ketoglutarate

histidine→	Urocanic acid Imidazol-4-one-5-propionic acid Formiminoglutamic acid Glutamate-1-semialdehyde
proline→	1-Pyrroline-5-carboxylic acid
arginine→	Agmatine Ornithine Citrulline Cadaverine Putrescine
other	cysteine+glutamate→glutathione:γ-Glutamylcysteine

G→propionyl-CoA→
succinyl-CoA

valine→	α-Ketoisovaleric acid Isobutyryl-CoA Methacrylyl-CoA 3-Hydroxyisobutyryl-CoA 3-Hydroxyisobutyric acid 2-Methyl-3-oxopropanoic acid
isoleucine→	2,3-Dihydroxy-3-methylpentanoic acid 2-Methylbutyryl-CoA Tiglyl-CoA 2-Methylacetoacetyl-CoA
methionine→	generation of homocysteine:S-Adenosyl methionine S-Adenosyl-L-homocysteine Homocysteine conversion to cysteine:Cystathionine α-Ketobutyric acid +Cysteine
threonine→	α-Ketobutyric acid
propionyl-CoA→	Methylmalonyl-CoA

phenylalanine→tyrosine→	4-Hydroxyphenylpyruvic acid Homogentisic acid 4-Maleylacetoacetic acid

G→oxaloacetate

seeurea cycle

Other

Cysteine metabolism	Cysteine sulfinic acid

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Amino acids

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