File:L-Threonin_-_L-Threonine.svg · Wikimedia Commons · See Wikimedia Commons
L-threonine
Sign in to saveAlso known as Thr, T, L-Threonin, L-(-)-Threonine, L-2-Amino-3-hydroxybutyric acid, (2S,3R)-(-)-Threonine, (2S)-threonine, 2-Amino-3-hydroxybutyric acid
Threonine (symbol Thr or T) is an amino acid that is used in the biosynthesis of proteins. It contains an α-amino group (which is in the protonated −NH form when dissolved in water), a carboxyl group (which is in the deprotonated −COO− form when dissolved in water), and a side chain containing a hydroxyl group, making it a polar, uncharged amino acid. It is essential in humans, meaning the body cannot synthesize it: it must be obtained from the diet. Threonine is synthesized from aspartate in bacteria such as E. coli. It is encoded by all the codons starting AC (ACU, ACC, ACA, and ACG).
OverviewAI-generated
L-threonine is a chemical compound with the formula C₄H₉NO₃. Its IUPAC name is (2S,3R)-2-azaniumyl-3-hydroxybutanoate. The substance has a mass of 119.058 and a melting point of 256.
Chemical properties include an xlogp value of -2.3 and a topological polar surface area of 88. The molecule contains two hydrogen bond donors and three hydrogen bond acceptors. Its canonical SMILES representation is CC(C(C(=O)O)N)O, while the isomeric SMILES is C[C@H]([C@@H](C(=O)O)N)O.
The compound is associated with a Commons category titled "Threonine." It has been referenced by 1,145 other encyclopedia articles. A search for L-threonine in PubMed yields 153,597 results.
Synthesized by Vinony from 20 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
- C4H9NO3
- Molecular weight
- 119.12 g/mol
- IUPAC name
- (2S,3R)-2-azaniumyl-3-hydroxybutanoate
- SMILES
- C[C@H]([C@@H](C(=O)[O-])[NH3+])O
- InChIKey
- AYFVYJQAPQTCCC-GBXIJSLDSA-N
- XLogP
- -2.3
- Polar surface area
- 88 Ų
- H-bond donors
- 2
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Research
153,597 papers- Microbial Production of l-Threonine Using Metabolically Engineered Escherichia coli.ReviewJournal of agricultural and food chemistry · 2025Nie Y, Tian Y, Ren X et al.DOI: 10.1021/acs.jafc.5c01453
- Construction of L-lysine-, L-threonine-, and L-isoleucine-overproducing strains of Corynebacterium glutamicum.ReviewAnnals of the New York Academy of Sciences · 1996Sahm H, Eggeling L, Eikmanns B et al.DOI: 10.1111/j.1749-6632.1996.tb40544.x
- Peculiarities of promiscuous L-threonine transaldolases for enantioselective synthesis of β-hydroxy-α-amino acids.ReviewApplied microbiology and biotechnology · 2021Wang S, Deng HDOI: 10.1007/s00253-021-11288-w
- Engineering Halomonas bluephagenesis for L-Threonine production.Metabolic engineering · 2020Du H, Zhao Y, Wu F et al.DOI: 10.1016/j.ymben.2020.04.004
- L-threonine promotes healthspan by expediting ferritin-dependent ferroptosis inhibition in C. elegans.Nature communications · 2022Kim J, Jo Y, Cho D et al.DOI: 10.1038/s41467-022-34265-x
- Microbial metabolic engineering for L-threonine production.ReviewSub-cellular biochemistry · 2012Dong X, Quinn PJ, Wang XDOI: 10.1007/978-94-007-5055-5_14
- Transcriptomic analysis of an l-threonine-producing Escherichia coli TWF001.Biotechnology and applied biochemistry · 2020Zhao L, Zhang H, Wang X et al.DOI: 10.1002/bab.1890
- Multifunctionality of a low-specificity L-threonine aldolase from the hyperthermophile Thermotoga maritima.Extremophiles : life under extreme conditions · 2024Miyamoto T, Kobayashi F, Emori K et al.DOI: 10.1007/s00792-024-01357-z
via PubMed
Wikidata facts
- Has part
- nitrogen
- Named after
- D-threose
- Mass
- 119.058
- Has use
- medication
Show 6 more facts
- Commons category
- Threonine
- found in taxon
- Rhynchospora colorata
- chemical formula
- C₄H₉NO₃
- canonical SMILES
- CC(C(C(=O)O)N)O
- isomeric SMILES
- C[C@H]([C@@H](C(=O)O)N)O
- melting point
- 256
Sources (3)
via Wikidata · CC0
~7 min read
Encyclopedic overview
12 sectionsContents
- Modifications
- History
- Stereoisomers
- Biosynthesis
- Metabolism
- Metabolic diseases
- Evolutionary significance
- Research of Threonine as a Dietary Supplement in Animals
- Exploration of L-Threonine for Tuberculosis
- Sources
- References
- External links
Threonine (symbol Thr or T) is an amino acid that is used in the biosynthesis of proteins. It contains an α-amino group (which is in the protonated −NH form when dissolved in water), a carboxyl group (which is in the deprotonated −COO− form when dissolved in water), and a side chain containing a hydroxyl group, making it a polar, uncharged amino acid. It is essential in humans, meaning the body cannot synthesize it: it must be obtained from the diet. Threonine is synthesized from aspartate in bacteria such as E. coli. It is encoded by all the codons starting AC (ACU, ACC, ACA, and ACG).
Threonine sidechains are often hydrogen bonded; the most common small motifs formed are based on interactions with serine: ST turns, ST motifs (often at the beginning of alpha helices) and ST staples (usually at the middle of alpha helices).
Excerpted from Wikipedia’s “L-threonine” article, available under the CC BY-SA 4.0 licence.
Gallery (18)
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