119736-88-8

Usage

Uses

Used in Pharmaceutical Industry:
L-Homoserine is used as a precursor in the biosynthesis of antibiotics, such as penicillin, for its essential role in the production of these life-saving drugs.
Used in Biochemical Research:
L-Homoserine is utilized as a research tool for studying the metabolic pathways and biosynthesis of essential amino acids, threonine and methionine, which are critical for protein synthesis and other biochemical processes.
Used in Neurodegenerative Disease Treatment:
L-Homoserine is explored as a potential therapeutic agent for treating neurodegenerative diseases, given its involvement in biochemical processes that may contribute to the development or progression of such conditions.
Used in Cancer Therapy:
L-Homoserine is investigated for its potential applications in cancer treatment, as it may play a role in the regulation of cellular processes that are disrupted in cancer cells.
Used in Drug Delivery and Targeting:
L-Homoserine is employed in the development of new strategies for drug delivery and targeting specific cells and tissues, leveraging its biochemical properties to enhance the efficacy and selectivity of therapeutic agents.

Upstream product

• 348-67-4 D-methionine 
• 206194-18-5 3-amino-3-furan-2-ylpropan-1-ol 
• 3493-10-5 (2R)-methionine methysulfonium iodide 
• 50-00-0 formaldehyd 
• 338-69-2 D-Alanine 
• 63-68-3 L-methionine 
• 87625-62-5 ptaquiloside 
• 33515-32-1 S-methyl-L-methionine hydrobromide 
• 96293-17-3 (S)-N-(2-benzoylphenyl)-1-benzylpyrrolidine-2-carboxamide 
• 56-40-6 glycine 
• 159487-41-9 Isopropyl (2S)-N-(trifluoroacetyl)homoserine 
• 2185-03-7 L-homoserine lactone hydrochloride 
• 2185-02-6 L-homoserine lactone 
• 6708-35-6 [14C]-S-methyl-L-Methionine 

Downstream Products

• 745011-75-0 (R)-2-((tert-butoxycarbonyl)amino)-4-hydroxybutanoic acid 
• 41088-87-3 N-benzoyl-L-homoserine 
• 4096-48-4 O-oxalylhomoserine 
• 116786-66-4 Methyl 4,6-Dideoxy-4-<(S)-2,4-dihydroxybutanamido>-α-D-mannopyranoside 
• 134863-57-3 C₁₁H₉N₃O₆⁽¹⁸⁾O 
• 134863-58-4 C₁₁H₉N₃O₅⁽¹⁸⁾O₂ 
• 796072-25-8 (L)-N-tert-butoxycarbonylhomoserine triethylamine salt 
• 120042-11-7 methyl (S)-4-hydroxy-2-((tert-butoxy)carbonylamino)-butyrate 
• 15159-65-6 (2S)-2-amino-4-bromobutanoic acid hydrobromide 
• 51524-71-1 2,2-dichloro-N-[(3S)-tetrahydro-2-oxo-3-furanyl]-acetamide 
• 7540-67-2 O-acetyl-L-homoserine 
• 7471-52-5 5-(β-bromoethyl)hydantoin 
• 38308-93-9 2-tert-butoxycarbonylamino-4-hydroxy-butyric acid benzyl ester 
• 38308-92-8 2-(tert-butoxycarbonylamino)-4-hydroxy-butanoic acid 

Relevant academic research and scientific papers

Ds-ERYTHRO-2-AMINO-4-ETHOXY-3-HYDROXYBUTANOIC ACID FROM THE FRUITING BODIES OF THE EDIBLE MUSHROOM, LYOPHYLLUM ULMARIUM

A new β-hydroxy amino acid isolated from the fruiting bodies of Lyophyllum ulmarium was identified as Ds-erythro-2-amino-4-ethoxy-3-hydroxybutanoic acid by chemical degradation and spectroscopic analyses. Key Word Index - Lyophyllum ulmarium; Tricholomataceae; mushroom; amino acid; Ds-erythro-2-amino-4-ethoxy-3-hydroxybutanoic acid.

Reaction of (S)-homoserine lactone with Grignard reagents: synthesis of amino-keto-alcohols and β-amino acid derivatives

The ring-opening reaction of homoserine lactone with phenylmagnesium bromides was systematically examined. A reliable method to achieve β-amino acid precursors was developed by tuning the reaction conditions to favor mono-addition to the carbonyl moiety of the lactone.

Large-scale, protection-free synthesis of Se-adenosyl-l-selenomethionine analogues and their application as cofactor surrogates of methyltransferases

S-Adenosyl-l-methionine (SAM) analogues have previously demonstrated their utility as chemical reporters of methyltransferases. Here we describe the facile, large-scale synthesis of Se-alkyl Se-adenosyl-l-selenomethionine (SeAM) analogues and their precursor, Se-adenosyl-l-selenohomocysteine (SeAH). Comparison of SeAM analogues with their equivalent SAM analogues suggests that sulfonium-to-selenonium substitution can enhance their compatibility with certain protein methyltransferases, favoring otherwise less reactive SAM analogues. Ready access to SeAH therefore enables further application of SeAM analogues as chemical reporters of diverse methyltransferases.

Selective Inhibition of Benzyl Ether Hydrogenolysis with Pd/C Due to the Presence of Ammonia, Pyridine or Ammonium Acetate

Ammonia, pyridine and ammonium acetate were found to be extremely effective as inhibitors of Pd/C catalyzed benzyl ether hydrogenolysis.While olefin, Cbz, benzyl ester and azide functionalities were hydrogenated smoothly, benzyl ethers were not cleaved in the presence of these additives.

Radiation chemical studies of methionine in aqueous solution: Understanding the role of molecular oxygen

The oxidation of methionine is an important reaction in the biological milieu. Despite a few decades of intense studies, several fundamental aspects remain to be defined. We have investigated in detail the γ-radiolysis of free methionine in the absence and presence of molecular oxygen followed by product characterization and quantification. The primary site of attack by HO? radicals and H? atoms is the sulfur atom of methionine. We have disclosed that HO? radicals do not oxidize methionine to the corresponding sulfoxide in either the presence or the absence of oxygen; the oxidizing species is H2O2 derived either from the radiolysis of water or from the disproportionation of the byproduct O2?-. 3-Methylthiopropionaldehyde is the major product of HO? radical attack in the presence of molecular oxygen. Together with the direct oxidation at sulfur as the major product, the potential of H? atoms is also proven to be highly specific for sulfur atom attack under anoxic and aerobic conditions. The major products derived from the H? atoms attack are found to be α-aminobutyric acid or homoserine, in the absence or presence of oxygen, respectively. All together, these results help clarify the fate of methionine related to a biological environment and offer a molecular basis for envisaging other possible pathways of in vivo degradation as well as other markers.

Concise Synthesis of Enantiomerically Pure (1′S,2′R)-and (1′R,2′S)-2S-Amino-3-(2′-aminomethyl-cyclopropyl)propionic Acid: Two E-Diastereoisomers of 4,5-Methano-l-lysine

A concise synthesis of both E-isomers of 2S-amino-3-(2′-aminomethyl- cyclopropyl)propionic acid, new methano-l-lysines, is described. The synthetic route includes nine steps from l-methionine, with a key step involving the cyclopropanation of an intermediate E-allylic alcohol. The resultant hydroxymethylcyclopropanes were readily separated and converted into the title α-amino acids. The stereochemistry around the cyclopropane rings was deduced by conducting the cyclopropanation in the presence of N,N,N′,N′-tetramethyl-d-tartaric acid diamide butylboronate, a chiral controller which is known to favour the production of S-hydroxymethyl cyclopropanes from allylic alcohols.

Synthesis of L-(+)-selenomethionine

A novel three-pot synthesis of L-(+)-selenomethionine suitable for small and large scale preparations is presented. The method gives high optical purity and avoids evil smelling selenium species.

Chemical approach for interconversion of (S)- and (R)-α-amino acids

Here we report a general method for the preparation of unnatural (R)-α-amino acids via complexation of α-(phenyl)ethylamine derived chiral reagent (S)-3 with various (S)-α-amino acids. The reactions proceed with synthetically useful chemical yields and thermodynamically controlled diastereoselectivity. Chiral reagent (S)-3 can be conveniently recovered and reused without any loss of enantiomeric purity and reactivity. The Royal Society of Chemistry 2013.

Structure of the O-antigen of Acinetobacter lwoffii EK30A; Identification of d-homoserine, a novel non-sugar component of bacterial polysaccharides

We established a peculiar structure of the O-specific polysaccharide (O-antigen) of a psychrotrophic strain of Acinetobacter lwoffii, EK30A, isolated from a 1.6-1.8 million-year-old Siberian permafrost subsoil sediment sample. The polysaccharide was released by mild acid degradation of the lipopolysaccharide and studied using chemical analyses, Smith degradation, 1H and 13C NMR spectroscopy and mass spectrometry. It was found to contain d-homoserine, which is N-linked to 4-amino-4,6-dideoxy-d- glucose (Qui4N) and is N-acylated itself with acetyl in about half of the repeating units or (S)-3-hydroxybutanoyl group in the other half. The following is the structure of the tetrasaccharide repeating unit of the polysaccharide: →3)-β-d-Quip4NAcyl-(1→6)-α-d-Galp-(1→4) -α-d-GalpNAc-(1→3)-α-d-FucpNAc-(1→ where Acyl stands for either N-acetyl- or N-[(S)-3-hydroxybutanoyl]-d-homoseryl. The Royal Society of Chemistry 2010.

A selective method for sequential splitting of O- and N-linked glycans from N,O-glycoproteins

O-linked oligosaccharides from N,O-glycoproteins were selectively split off by treatment with alkaline sodium borohydride in the presence of cadmium salt.The side reaction of reductive cleavage of N-glycosylamide and peptide bonds, observed under standard conditions of splitting of O-linked chains (M NaBH4 and 50mM NaOH, 16 h, 50 deg C), was inhibited by addition of 5-10 mM cadmium acetate and 5-10 mM EDTA*Na4, as shown by treatment of model compounds and several glycoproteins (ovomucoid, group-specific glycoproteins H and B, fetuin, and asialofetuin).This treatment,in combination with the previously developed prodcdure for the release of the N-linked oligosaccharide chains by lithium borohydride, allows a sequential, selective cleavage of O-, and then N-linked oligosaccharides from N,O-glycoproteins by chemical methods.