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L-leucine

File:L-Leucine.svg · Wikimedia Commons · See Wikimedia Commons

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L-leucine

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Also known as L-Leu, (2S)-2-amino-4-methylpentanoic acid, (S)-(+)-leucine, (S)-leucine, (2S)-2-amino-4-methyl-pentanoic acid, L-alpha-Aminoisocaproic acid, L, (S)-2-amino-4-methylpentanoic acid

thumb|Leucine ball and stick model spinning Leucine or leucin (symbol Leu or L) is an essential amino acid that is used in the biosynthesis of proteins. Leucine is an α-amino acid, meaning it contains an α-amino group (which is in the protonated −NH3+ form under biological conditions), an α-carboxylic acid group (which is in the deprotonated −COO− form under biological conditions), and a side chain isobutyl group, making it a non-polar aliphatic amino acid. It is essential in humans, meaning the body cannot synthesize it; it must be obtained from the diet. Human dietary sources are foods that

OverviewAI-generated

L-leucine is a chemical compound with the formula C₆H₁₃NO₂. Its IUPAC name is (2S)-2-azaniumyl-4-methylpentanoate. The substance has a mass of 131.095 and a weight of 131.17. It possesses a charge of 0, an xlogp of -0.9, and a tpsa of 67.8. The molecule contains one hydrogen bond donor and two hydrogen bond acceptors.

The compound is identified by the canonical SMILES string CC(C)CC(C(=O)O)N and the isomeric SMILES string CC(C)C[C@@H](C(=O)O)N. Its PubChem identifier is 7045798, and it is associated with the InChIKey ROHFNLRQFUQHCH-YFKPBYRVSA-N. A search for L-leucine in PubMed yields 99,913 results. The subject is referenced by 1,047 other encyclopedia articles.

Synthesized by Vinony from 18 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
C6H13NO2
Molecular weight
131.17 g/mol
IUPAC name
(2S)-2-azaniumyl-4-methylpentanoate
SMILES
CC(C)C[C@@H](C(=O)[O-])[NH3+]
InChIKey
ROHFNLRQFUQHCH-YFKPBYRVSA-N
XLogP
-0.9
Polar surface area
67.8 Ų
H-bond donors
1
H-bond acceptors
2
Formal charge
0

via PubChem

Research

99,913 papers

via PubMed

~7 min read

Encyclopedic overview

14 sections
Contents
  • Dietary leucine
  • Requirements
  • Sources {{Anchor|Dietary sources}}
  • Health effects
  • Safety
  • Pharmacology
  • Pharmacodynamics
  • Metabolism in humans
  • Synthesis in nonhuman organisms
  • Chemistry
  • See also
  • Notes
  • References
  • External links

thumb|Leucine ball and stick model spinning Leucine or leucin (symbol Leu or L) is an essential amino acid that is used in the biosynthesis of proteins. Leucine is an α-amino acid, meaning it contains an α-amino group (which is in the protonated −NH3+ form under biological conditions), an α-carboxylic acid group (which is in the deprotonated −COO− form under biological conditions), and a side chain isobutyl group, making it a non-polar aliphatic amino acid. It is essential in humans, meaning the body cannot synthesize it; it must be obtained from the diet. Human dietary sources are foods that contain protein, such as meats, dairy products, soy products, and beans and other legumes. It is encoded by the codons UUA, UUG, CUU, CUC, CUA, and CUG. Leucine is named after the Greek word for 'white': λευκός (leukós 'white'), after its common appearance as a white powder, a property it shares with many other amino acids.

Like valine and isoleucine, leucine is a branched-chain amino acid. The primary metabolic end products of leucine metabolism are acetyl-CoA and acetoacetate; consequently, it is one of the two exclusively ketogenic amino acids, with lysine being the other. It is the most important ketogenic amino acid in humans.

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

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