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: 2024-11-05 08:26:49
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) |
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 |
Abamectin manufacturer
JSK Chemicals
Sami Sabinsa Group Limited (formerly Sami Labs Limited)
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