DL-methionine

Also known as Met, M, 2-amino-4-(methylthio)butanoic acid, Methionine, Hmet, alpha-amino-gamma-methylmercaptobutyric acid, 2-amino-4-(methylsulfanyl)butanoic acid, Racemethionine

thumb|Methionine ball and stick model spinning Methionine (symbol Met or M) () is an essential amino acid in humans. Compared to other amino acids, methionine has particularly decisive biosynthetic roles. It is the precursor to the amino acid cysteine and the pervasive methylation agent rSAM. Methionine is required for protein synthesis, which is initiated by N-formylmethionine-sRNA.

OverviewAI-generated

DL-methionine is a chemical compound with the formula C₅H₁₁NO₂S. Its canonical SMILES notation is CSCCC(C(=O)O)N, and it has a mass of 149.05105. The substance exhibits a density of 1.340 and a pKa of 2.29.

According to PubChem data, the compound has a weight of 149.21 and a topological polar surface area of 91.5. It features two hydrogen bond donors and four hydrogen bond acceptors, with a charge of 0. The xlogp value is -1.2, and its IUPAC name is 2-amino-4-methylsulfanylbutanoate;hydron.

The subject is associated with a Commons category titled "Methionine." It has been referenced by 1,418 other encyclopedia articles, and a PubMed query for DL-methionine returns a count of 2221.

Synthesized by Vinony from 19 facts across 4 sources: Wikidata, PubMed, PubChem, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.

Chemical data

Formula: C5H11NO2S
Molecular weight: 149.21 g/mol
IUPAC name: 2-azaniumyl-4-methylsulfanylbutanoate
SMILES: CSCCC(C(=O)[O-])[NH3+]
InChIKey: FFEARJCKVFRZRR-UHFFFAOYSA-N
XLogP: -1.2
Polar surface area: 93.1 Å²
H-bond donors: 1
H-bond acceptors: 3
Formal charge: 0

via PubChem

Research

2,221 papers

Assessing the nutritional equivalency of DL-methionine and L-methionine in broiler chickens: a meta-analytical study.Poultry science · 2023
Relative bioavailability of L-methionine and DL-methionine in growing broilers.Poultry science · 2024
Intermittent dietary methionine deprivation facilitates tumoral ferroptosis and synergizes with checkpoint blockade.Nature communications · 2023
Glycine and aging: Evidence and mechanisms.Ageing research reviews · 2023
Resolution of N-acetyl-DL-methionine methyl ester by the lipase from Brucella thiophenivorans.Chirality · 2024

via PubMed

~14 min read

Encyclopedic overview

22 sections

Contents

Biochemical details
A proteinogenic amino acid
Encoding
Derivatives
''S''-Adenosylmethionine
Biosynthesis
Transsulfurylation pathway
Other biochemical pathways
Catabolism
Regeneration
Reverse-transulfurylation pathway: conversion to cysteine
Metabolic diseases
Chemical synthesis
Human nutrition
Requirements
Dietary sources
Health
Other uses
Restricting methionine intake
See also
References
External links

Methionine was first isolated in 1921 by John Howard Mueller. It is encoded by the codon AUG. It was named by Satoru Odake in 1925, as an abbreviation of its structural description 2-amino-4-(methylthio)butanoic acid.

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