L-alanine

Also known as L-Ala, L-alpha-Alanine, L-α-alanine, (2S)-2-aminopropanoic acid, (S)-alanine, (S)-2-aminopropanoic acid, alanine, L-2-aminopropionic acid

thumb|Spin view of ball-stick model Alanine (symbol Ala or A), or α-alanine, is an α-amino acid that is used in the biosynthesis of proteins. It contains an amine group and a carboxylic acid group, both attached to the central carbon atom which also carries a methyl group side chain. Consequently it is classified as a non-polar, aliphatic α-amino acid. Under biological conditions, it exists in its zwitterionic form with its amine group protonated (as ) and its carboxyl group deprotonated (as ). It is non-essential to humans as it can be synthesized metabolically and does not need to be present

AI overview

L-alanine is a simple amino acid—one of the building blocks used to make proteins in living organisms—that contains an amine group, a carboxylic acid group, and a methyl side chain all connected to a central carbon atom. It is non-essential for humans because our bodies can produce it on their own, so we don't need to obtain it from food sources.

AI-generated from the Wikipedia summary — may contain errors.

Chemical data

Formula: C3H7NO2
Molecular weight: 89.09 g/mol
IUPAC name: (2S)-2-aminopropanoic acid
SMILES: C[C@@H](C(=O)O)N
InChIKey: QNAYBMKLOCPYGJ-REOHCLBHSA-N
XLogP: -3
Polar surface area: 63.3 Å²
H-bond donors: 2
H-bond acceptors: 3
Formal charge: 0

via PubChem

Research

152,975 papers

Metabolic engineering of microorganisms for L-alanine production.ReviewJournal of industrial microbiology & biotechnology · 2022Liu P, Xu H, Zhang XDOI: 10.1093/jimb/kuab057
Exogenous L-Alanine promotes phagocytosis of multidrug-resistant bacterial pathogens.EMBO reports · 2023Jiang M, Chen XH, Li H et al.DOI: 10.15252/embr.201949561
l-Alanine Exporter AlaE Functions as One of the d-Alanine Exporters in Escherichia coli.International journal of molecular sciences · 2023Katsube S, Sakai K, Ando T et al.DOI: 10.3390/ijms241210242
The effect of L-alanine on sleep through taste properties in Drosophila melanogaster.Neuroscience research · 2025Garibağaoğlu R, Kobayashi R, Hanashiro V et al.DOI: 10.1016/j.neures.2025.104924
L-Alanine promotes anti-infectious properties of Bacillus subtilis S-2 spores via the germination receptor gerAA.Probiotics and antimicrobial proteins · 2024Lu S, Liao X, Lu W et al.DOI: 10.1007/s12602-023-10121-2
Enzymatic determination of d-alanine with l-alanine dehydrogenase and alanine racemase.Bioscience, biotechnology, and biochemistry · 2021Ashida H, Sawa Y, Yoshimura TDOI: 10.1093/bbb/zbab148
L-alanine supplementation improves blood glucose level and biochemical indices in alloxan-induced diabetic rats.Journal of food biochemistry · 2021Dandare SU, Ezeonwumelu IJ, Shinkafi TS et al.DOI: 10.1111/jfbc.13590
Studies on beta-(pyrazolyl-n)-L-alanine.The Journal of biological chemistry · 1963TAKESHITA M, NISHIZUKA Y, HAYAISHI O

via PubMed

Wikidata facts

Mass: 89.048

Show 7 more facts

pKa: 2.61
chemical formula: C₃H₇NO₂
Commons category: L-Alanine
canonical SMILES: CC(C(=O)O)N
melting point: 314.5
NCI Thesaurus ID: C29605
isomeric SMILES: C[C@H](N)C(O)=O

Sources (3)

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~9 min read

Article

13 sections

Contents

History and etymology
Structure
Sources
Biosynthesis
Chemical synthesis
Degradation
Alanine world hypothesis
Physiological function
Glucose–alanine cycle
Link to diabetes
Chemical properties
Free radical
References

The L-isomer of alanine (left-handed) is the one that is incorporated into proteins. L-alanine is second only to L-leucine in rate of occurrence, accounting for 7.8% of the primary structure in a sample of 1,150 proteins. The right-handed form, D-alanine, occurs in peptides in some bacterial cell walls (in peptidoglycan) and in some peptide antibiotics, and occurs in the tissues of many crustaceans and molluscs as an osmolyte.