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Topic summary

Threonine

Threonine
Names IUPAC name
Threonine
Systematic IUPAC name
2-Amino-3-hydroxybutanoic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard100.000.704EC Number
  • L: 200-774-1
KEGG
UNII
  • InChI=1S/C4H9NO3/c1-2(6)3(5)4(7)8/h2-3,6H,5H2,1H3,(H,7,8)/t2-,3+/m1/s1
    Key: AYFVYJQAPQTCCC-GBXIJSLDSA-N
  • D/L: Key: AYFVYJQAPQTCCC-FGNFWGHYNA-N
  • L: C[C@H]([C@@H](C(=O)O)N)O
  • L Zwitterion: C[C@H]([C@@H](C(=O)[O-])[NH3+])O
Properties C4H9NO3Molar mass119.120 g·mol (H2O, g/dl) 10.6(30°),14.1(52°),19.0(61°) Acidity (pKa) 2.63 (carboxyl), 10.43 (amino) Supplementary data page Threonine (data page)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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
3 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).

Wikipedia source