Homoserine

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l-Homoserine
Skeletal formula
Ball-and-stick model of the zwitterion
Names
IUPAC name
(S)-2-Amino-4-hydroxybutanoic acid
Identifiers
3D model (
JSmol
)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
 100.010.538 Edit this at Wikidata
EC Number
  • 211-590-6
UNII
  • InChI=1S/C4H9NO3/c5-3(1-2-6)4(7)8/h3,6H,1-2,5H2,(H,7,8) checkY
    Key: UKAUYVFTDYCKQA-UHFFFAOYSA-N checkY
  • InChI=1/C4H9NO3/c5-3(1-2-6)4(7)8/h3,6H,1-2,5H2,(H,7,8)
    Key: UKAUYVFTDYCKQA-UHFFFAOYAZ
  • O=C(O)C(N)CCO
Properties
C4H9NO3
Molar mass 119.12 g/mol
Melting point 203 °C (decomposes)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Homoserine (also called isothreonine) is an α-amino acid with the chemical formula HO2CCH(NH2)CH2CH2OH. L-Homoserine is not one of the common amino acids encoded by DNA. It differs from the proteinogenic amino acid serine by insertion of an additional -CH2- unit into the backbone. Homoserine, or its lactone form, is the product of a cyanogen bromide cleavage of a peptide by degradation of methionine.

Homoserine is an intermediate in the

L-aspartate-4-semialdehyde to L-homoserine. Then, two other enzymes, homoserine kinase and homoserine O-succinyltransferase use homoserine as a substrate and produce phosphohomoserine and O-succinyl homoserine respectively.[3]

Applications

Commercially, homoserine can serve as precursor to the synthesis of isobutanol and 1,4-butanediol.[4] Purified homoserine is used in enzyme structural studies.[5] Also, homoserine has played important roles in studies to elucidate peptide synthesis and synthesis of proteoglycan glycopeptides.[6] Bacterial cell lines can make copious amounts of this amino acid.[3][4]

Biosynthesis

Homoserine is produced from aspartate via aspartate-4-semialdehyde, which is produced from β-phosphoaspartate. By the action of homoserine dehydrogenases, the semialdehyde is converted to homoserine.[7]

Biosynthesis pathway for homoserine.

L-Homoserine is substrate for homoserine kinase, yielding phosphohomoserine (homoserine-phosphate), which is converted to by threonine synthase to yield L-threonine.

Homoserine is converted to O-succinyl homoserine by homoserine O-succinyltransferase, a precursor to L-methionine.[8]

Homoserine allosterically inhibits aspartate kinase and

α-ketoglutarate and α-ketoglutarate coverts to oxaloacetate through the citric cycle. Threonine acts as another allosteric inhibitor of aspartate kinase and homoserine dehydrogenase, but it is a competitive inhibitor of homoserine kinase.[8]

References

  1. ISSN 0002-1369
    .
  2. ISBN 0-7167-4684-0
  3. ^
    PMID 32801175
    .
  4. ^
    PMID 30002999
    .
  5. PMID 30423116
    .
  6. PMID 27809505
    .
  7. PMID 11352712
    .
  8. ^
    PMID 30023797
    .


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