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Homoserine

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Revision as of 23:04, 16 October 2011 by CheMoBot (talk | contribs) (Updating {{chembox}} (changes to verified fields - updated 'DrugBank_Ref', 'UNII_Ref', 'KEGG_Ref') per Chem/Drugbox validation (report errors or bugs))(diff) ← Previous revision | Latest revision (diff) | Newer revision → (diff)
L-Homoserine
Skeletal formula
Skeletal formula
Ball-and-stick model of the zwitterion
Ball-and-stick model of the zwitterion
Names
IUPAC name (S)-2-Amino-4-hydroxybutanoic acid
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.010.538 Edit this at Wikidata
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C4H9NO3/c5-3(1-2-6)4(7)8/h3,6H,1-2,5H2,(H,7,8)Key: UKAUYVFTDYCKQA-UHFFFAOYSA-N
  • InChI=1/C4H9NO3/c5-3(1-2-6)4(7)8/h3,6H,1-2,5H2,(H,7,8)Key: UKAUYVFTDYCKQA-UHFFFAOYAZ
SMILES
  • O=C(O)C(N)CCO
Properties
Chemical formula C4H9NO3
Molar mass 119.12 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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 methylene group. 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 biosynthesis of three essential amino acids: methionine, threonine (an isomer of homoserine), and isoleucine. It forms by two reductions of aspartic acid via the intermediacy of aspartate semialdehyde.

References

  1. Berg, J. M.; Stryer, L. et al. (2002), Biochemistry. W.H. Freeman. ISBN 0-7167-4684-0


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