ChemicalBook Product Catalog Biochemical Engineering Amino Acids and Derivatives α-Amino acid L-Homoserine

L-Homoserine

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
L-Homoserine Structure
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
pka2.71(at 25℃)
form Crystalline Powder
color White to light yellow
Water Solubility 1100 g/L (30 ºC)
Merck 14,4739
BRN 1721681
InChIKeyUKAUYVFTDYCKQA-VKHMYHEASA-N
LogP-1.289 (est)
CAS DataBase Reference672-15-1(CAS DataBase Reference)
Safety Information
Risk Statements 36/37/38
Safety Statements 24/25-44-35-26-28-7-4-3/9
WGK Germany 3
F 10
HS Code 29225000
MSDS Information
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L-Homoserine English
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ACROS English
ALFA English
L-Homoserine Usage And Synthesis
Chemical Propertieswhite to light yellow crystalline powder
UsesL-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.
DefinitionChEBI: 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 DescriptionL-Homoserine is a variant of serine with an additional carbon on its side chain.
Biochem/physiol ActionsL-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 MethodsLikely 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 ProductsDL-Threonine-->L-Lysine hydrochloride-->N-Fmoc-L-homoserine-->O-ACETYL-L-HOMOSERINE HYDROCHLORIDE
H-CIS-HYP-OME HCL AMASTATIN HYDROCHLORIDE H-ASP-OBZL HCL H-ASP(OTBU)-OTBU HCL DIMETHYL 5-(2,4-DICHLOROPHENYL)-4,6-DIOXOTETRAHYDRO-2H-PYRROLO[3,4-D]ISOXAZOLE-3,3(3AH)-DICARBOXYLATE H-HYP-OET HCL H-HYP-OBZL HCL AMASTATIN HYDROCHLORIDE MONOHYDRATE DIMETHYL 5-(4-CHLOROPHENYL)-4,6-DIOXOTETRAHYDRO-2H-PYRROLO[3,4-D]ISOXAZOLE-3,3(3AH)-DICARBOXYLATE H-ASP(OTBU)-OME HCL Dimethyl L-aspartate hydrochloride EPIAMASTATIN HCL H-ASP-OTBU HCL H-ASP(OBZL)-OTBU HCL 2-[(2-CHLOROACETYL)AMINO]SUCCINIC ACID H-ASP(OET)-OET HCL beta-Methyl L-aspartate hydrochloride DIMETHYL 5-(2-([3-CHLORO-5-(TRIFLUOROMETHYL)-2-PYRIDINYL]AMINO)ETHYL)-4,6-DIOXOTETRAHYDRO-2H-PYRROLO[3,4-D]ISOXAZOLE-3,3(3AH)-DICARBOXYLATE
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