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HomeProduct name listL-Homoserine

L-Homoserine

Synonym(s):(S)-2-Amino-4-hydroxybutyric acid;Hse;L-(-)-Homoserine

  • CAS NO.:672-15-1
  • Empirical Formula: C4H9NO3
  • Molecular Weight: 119.12
  • MDL number: MFCD00063090
  • EINECS: 211-590-6
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-19 23:02:33
L-Homoserine Structural

What is L-Homoserine?

Chemical properties

white to light yellow crystalline powder

The Uses of L-Homoserine

L-Homoserine is used in the biosynthesis of methionine, threonine and isoleucine. It is also used as an internal standard for neurotransmitter analysis and amino acids quantification.

Definition

ChEBI: L-homoserine is the L-enantiomer of homoserine. It has a role as a human metabolite, an algal metabolite, a Saccharomyces cerevisiae metabolite and an Escherichia coli metabolite. It is an enantiomer of a D-homoserine. It is a tautomer of a L-homoserine zwitterion.

Synthesis Reference(s)

Journal of the American Chemical Society, 80, p. 3147, 1958 DOI: 10.1021/ja01545a057
The Journal of Organic Chemistry, 24, p. 1794, 1959 DOI: 10.1021/jo01093a610

General Description

L-Homoserine is a variant of serine with an additional carbon on its side chain.

Biochem/physiol Actions

L-Homoserine is synthesized by deoxidation process, catalysed by homoserine dehydrogenase. This is one of the steps in the synthesis of L-threonine. The carbon flux in in bacteria such as E. coli is maintained by this reaction.

Purification Methods

Likely impurities are N-chloroacetyl-L-homoserine, N-chloroacetyl-D-homoserine, L-homoserine, homoserine lactone, homoserine anhydride (formed in strong solutions of homoserine if slightly acidic). It cyclises to the lactone in strongly acidic solution. It crystallises from water by adding 9 volumes of EtOH. [Greenstein & Winitz The Chemistry of the Amino Acids J. Wiley, Vol 3 pp 2612-2616 1961, Beilstein 4 IV 3187.]

Properties of L-Homoserine

Melting point: 203 °C (dec.)(lit.)
Boiling point: 222.38°C (rough estimate)
alpha  -8.5 º (c=2, H2O 22 ºC)
Density  1.3126 (rough estimate)
refractive index  1.4183 (estimate)
storage temp.  Store below +30°C.
solubility  1100g/l
form  Crystalline Powder
pka 2.71(at 25℃)
color  White to light yellow
Water Solubility  1100 g/L (30 ºC)
Merck  14,4739
BRN  1721681
CAS DataBase Reference 672-15-1(CAS DataBase Reference)

Safety information for L-Homoserine

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P271:Use only outdoors or in a well-ventilated area.
P280:Wear protective gloves/protective clothing/eye protection/face protection.

Computed Descriptors for L-Homoserine

InChIKey UKAUYVFTDYCKQA-VKHMYHEASA-N

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