L-homoserine - 672-15-1

L-homoserine

Catalog Number: EVT-248260
CAS Number: 672-15-1
Molecular Formula: C4H9NO3
Molecular Weight: 119.12 g/mol
The product is for non-human research only. Not for therapeutic or veterinary use.
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Product Introduction

Description
L-Homoserine is a non-proteinogenic amino acid that plays a crucial role in various biological processes. It is a precursor of threonine, an essential amino acid, and is involved in the biosynthesis of various secondary metabolites. L-Homoserine has also been found to exhibit potent biological activity, making it a promising candidate for drug development.
Applications in Various Fields
L-Homoserine has potential applications in medical, environmental, and industrial research. In medical research, L-homoserine can be used as a lead compound for drug development. It can also be used as a tool to study the regulation of gene expression and cell signaling pathways. In environmental research, L-homoserine can be used to study the effects of pollutants on ecosystems and to develop sustainable pollution management strategies. In industrial research, L-homoserine can be used to improve the efficiency and quality of manufacturing processes. It can also be used to develop new products with enhanced biological activity.

Properties

CAS Number

672-15-1

Product Name

L-homoserine

IUPAC Name

(2S)-2-amino-4-hydroxybutanoic acid

Molecular Formula

C4H9NO3

Molecular Weight

119.12 g/mol

InChI

InChI=1S/C4H9NO3/c5-3(1-2-6)4(7)8/h3,6H,1-2,5H2,(H,7,8)/t3-/m0/s1

InChI Key

UKAUYVFTDYCKQA-VKHMYHEASA-N

SMILES

C(CO)C(C(=O)O)N

Solubility

1000000 mg/L (at 30 °C)
8.39 M
1000.0 mg/mL

Synonyms

L-homoserine;672-15-1;(s)-2-amino-4-hydroxybutanoicacid;(s)-homoserine;(S)-2-Amino-4-hydroxybutyricacid;(2S)-2-amino-4-hydroxybutanoicacid;h-hoser-oh;Homoserine(VAN);2-Amino-4-hydroxybutyricacid;2-amino-4-hydroxybutyrate;UNII-6KA95X0IVO;2-amino-4-hydroxy-Butyrate;2-amino-4-hydroxy-L-Butyrate;2-amino-4-hydroxy-Butyricacid;CHEBI:15699;(S)-2-Amino-4-hydroxybutanoate;2-amino-4-hydroxybutanoate;UKAUYVFTDYCKQA-VKHMYHEASA-N;(S)-2-amino-4-hydroxy-Butanoate;2-amino-4-hydroxy-L-Butyricacid;MFCD00063090;(S)-2-amino-4-hydroxy-Butanoicacid;HSE;(2S)-2-amino-4-hydroxy-butanoicacid;Butanoicacid,2-amino-4-hydroxy-,(S)-

Canonical SMILES

C(CO)C(C(=O)[O-])[NH3+]

Isomeric SMILES

C(CO)[C@@H](C(=O)[O-])[NH3+]
Method of Synthesis or Extraction
L-Homoserine can be synthesized by various methods, including chemical synthesis, enzymatic synthesis, and microbial fermentation. Chemical synthesis involves the reaction of acetaldehyde with ammonium acetate, followed by hydrolysis to yield L-homoserine. Enzymatic synthesis involves the use of enzymes such as threonine aldolase and serine hydroxymethyltransferase to catalyze the conversion of glycine and acetaldehyde to L-homoserine. Microbial fermentation involves the use of microorganisms such as Escherichia coli and Corynebacterium glutamicum to produce L-homoserine from glucose or other carbon sources.
The efficiency and yield of each method vary depending on the conditions used. Chemical synthesis has been reported to yield L-homoserine with a purity of up to 99%, but it requires toxic reagents and generates hazardous waste. Enzymatic synthesis has been found to be more environmentally friendly, but it requires expensive enzymes and may have lower yields. Microbial fermentation is a cost-effective and sustainable method, but it requires optimization of the fermentation conditions to achieve high yields.
Chemical Structure and Biological Activity
L-Homoserine has a chemical structure similar to that of serine, with an additional methylene group between the amino and carboxyl groups. This structural difference gives L-homoserine unique biological activity. L-Homoserine has been found to exhibit antimicrobial, antitumor, and anti-inflammatory activity. It has also been shown to modulate cell signaling pathways and regulate gene expression.
Biological Effects
L-Homoserine has been found to affect various cellular processes, including cell proliferation, differentiation, and apoptosis. It has been shown to modulate the activity of enzymes involved in the biosynthesis of threonine and other amino acids. L-Homoserine has also been found to regulate the expression of genes involved in the immune response and inflammation.
Potential therapeutic and toxic effects:
L-Homoserine has shown promising results in preclinical studies as a potential therapeutic agent for various diseases, including cancer, bacterial infections, and inflammatory disorders. However, its toxicity and safety profile need to be further evaluated in clinical trials.
Future Perspectives and Challenges
The use of L-homoserine in scientific research is still limited by the lack of efficient and cost-effective methods for its synthesis or extraction. Further research is needed to optimize the existing methods and to develop new methods for the production of L-homoserine. The potential therapeutic and toxic effects of L-homoserine need to be further evaluated in clinical trials. The development of new applications for L-homoserine in medical, environmental, and industrial research will require interdisciplinary collaborations and innovative approaches.

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