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L-alanine

File:L-Alanin_-_L-Alanine.svg · Wikimedia Commons · See Wikimedia Commons

EntityQ218642· pop 74· linked from 1,542 articles

L-alanine

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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

OverviewAI-generated

L-alanine, also identified as (2S)-2-aminopropanoic acid, is a chemical compound with the formula C₃H₇NO₂. It has a mass of 89.048 and a melting point of 314.5. The compound features a pKa of 2.61 and a charge of 0. Its structural properties include two hydrogen bond donors and three hydrogen bond acceptors, with a topological polar surface area of 63.3 and an xlogp value of -3.

The substance is represented by the canonical SMILES string CC(C(=O)O)N and the isomeric SMILES C[C@H](N)C(O)=O. It is cataloged in the NCI Thesaurus under the ID C29605 and has a PubChem CID of 5950. A search for L-alanine in PubMed yields 152,975 results. Additionally, the subject is referenced by 1,542 other encyclopedia articles.

Synthesized by Vinony from 22 facts across 4 sources: Wikidata, PubChem, PubMed, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still 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 Ų
H-bond donors
2
H-bond acceptors
3
Formal charge
0

via PubChem

Research

152,975 papers

via PubMed

~9 min read

Encyclopedic overview

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

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 in the diet. It is encoded by all codons starting with GC (GCU, GCC, GCA, and GCG).

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.

Excerpted from Wikipedia’s “L-alanine” article, available under the CC BY-SA 4.0 licence.

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