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L-Homoserine

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L-Homoserine Basic information

Product Name:
L-Homoserine
Synonyms:
  • (S)-(-)-2-AMINO-4-HYDROXYBUTYRIC ACID
  • (S)-2-AMINO-4-HYDROXYBUTYRIC ACID
  • L-2-AMINO-4-HYDROXYBUTANOIC ACID
  • L-2-AMINO-4-HYDROXYBUTYRIC ACID
  • L-2-AMINO-4-HYDROXYBUTYRIC ACID HYDROCHLORIDE
  • H-L-HSE-OH
  • H-HSE-OH
  • H-HOSER-OH
CAS:
672-15-1
MF:
C4H9NO3
MW:
119.12
EINECS:
211-590-6
Product Categories:
  • Serine [Ser, S]
  • Unusual Amino Acids
  • Amino Acids
  • Amino Acids & Derivatives
  • amino acids
  • bc0001
Mol File:
672-15-1.mol
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L-Homoserine Chemical Properties

Melting point:
203 °C (dec.)(lit.)
alpha 
-8.5 º (c=2, H2O 22 ºC)
Boiling point:
222.38°C (rough estimate)
Density 
1.3126 (rough estimate)
refractive index 
1.4183 (estimate)
storage temp. 
Store below +30°C.
solubility 
1100g/l
pka
2.71(at 25℃)
form 
Crystalline Powder
color 
White to light yellow
Water Solubility 
1100 g/L (30 ºC)
Merck 
14,4739
BRN 
1721681
InChIKey
UKAUYVFTDYCKQA-VKHMYHEASA-N
LogP
-1.289 (est)
CAS DataBase Reference
672-15-1(CAS DataBase Reference)
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Safety Information

Risk Statements 
36/37/38
Safety Statements 
24/25-44-35-26-28-7-4-3/9
WGK Germany 
3
10
HS Code 
29225000

MSDS

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L-Homoserine Usage And Synthesis

Chemical Properties

white to light yellow crystalline powder

Uses

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.]

L-Homoserine Preparation Products And Raw materials

Preparation Products

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