2185-03-7

Usage

Uses

Used in Pharmaceutical Industry:
L-Homoserine lactone hydrochloride is used as a precursor for the preparation of amino-keto-alcohols and β-amino acids, which are essential building blocks in the development of new pharmaceutical compounds. These molecules have potential applications in the treatment of various diseases and disorders.
Used in Chemical Synthesis:
L-Homoserine lactone hydrochloride is used as a starting material for the synthesis of L-discadenine, an important compound with potential applications in the development of new drugs and therapeutic agents.
Used in Biotechnology:
L-Homoserine lactone hydrochloride is used to prepare N-acylhomoserine lactone (AHL) analogs by reacting with substituted 2-chloro-N-phenylacetamide and different halides. AHLs are signaling molecules used by bacteria for quorum sensing, a communication mechanism that allows them to coordinate their behavior based on population density. The development of AHL analogs can lead to the creation of new biotechnological applications, such as the control of bacterial infections or the manipulation of bacterial behavior for industrial processes.

InChI:InChI=1/C4H5NO2.ClH/c5-3-1-2-7-4(3)6;/h1-3H,5H2;1H

Upstream product

• 657-19-2 (S)-N-trifluoroacetylaspartic acid-1-methyl ester 
• 498-19-1 L-(-)-homoserine 
• 63-68-3 L-methionine 
• 55154-48-8 (S)-N-(2-oxo-tetrahydrofuran-3-yl)-2-phenylacetamide 
• 79-11-8 chloroacetic acid 
• 96-34-4 methyl chloroacetate 
• 7540-67-2 O-acetyl-L-homoserine 
• 1492-23-5 O-succinyl-L-homoserine 
• 42417-39-0 (RS)-α-amino-γ-butyrolactone hydrochloride 
• 33693-66-2 α-Azido-γ-butyrolacton 
• 104347-03-7 2-Amino-4-(2-methoxy-ethoxymethoxy)-butyric acid methyl ester 
• 83427-81-0 (S)-N-tritylhomoserine lactone 
• 128669-50-1 (S)-2-hydroxyimino-3-(N-tritylamino)oxolane 
• 56-84-8 L-Aspartic acid 

Downstream Products

• 116857-07-9 (L)-N-Fmoc-homoserine lactone 
• 40856-59-5 tert-butyl (3S)-2-oxotetrahydrofuran-3-ylcarbamate 
• 672-15-1 L-homoserine 
• 216596-71-3 N-undecanoyl-L-homoserine lactone 
• 63-68-3 L-methionine 
• 202284-87-5 N-tetradecanoyl homoserine lactone 
• 96-48-0 4-butanolide 
• 3211-76-5 Seleno-L-methionine 
• 168982-69-2 N-(3-oxododecanoyl)-L-homoserine lactone 
• 147795-40-2 N-(3-oxodecanoyl)-L-homoserine lactone 
• 1446270-24-1 (S)-2-((4-chlorophenyl)amino)-2-oxoethyl(2-oxotetrahydrofuran-3-yl)carbamodithioate 
• 1446270-26-3 (S)-2-((4-bromophenyl)amino)-2-oxoethyl(2-oxotetrahydrofuran-3-yl)carbamodithioate 
• 1446270-33-2 (S)-2-oxo-2-(p-tolylamino)ethyl (2-oxotetrahydrofuran-3-yl)carbamodithioate 
• 1446270-32-1 (S)-2-((2-chlorophenyl)amino)-2-oxoethyl (2-oxotetrahydrofuran-3-yl)carbamodithioate 

Relevant academic research and scientific papers

L-GLUFOSINATE INTERMEDIATE AND L-GLUFOSINATE PREPARATION METHOD

Provided are L-glufosinate intermediate preparation method or L-glufosinate preparation method, the method, for preparing L-glufosinate intermediate or L-glufosinate from an L-homoserine derivative, comprising a step of preparing a compound of Chemical Formula 2 from a compound of Chemical Formula 1.

A Unified Approach to Phytosiderophore Natural Products

This work reports on the concise total synthesis of eight natural products of the mugineic acid and avenic acid families (phytosiderophores). An innovative ?east-to-west“ assembly of the trimeric products resulted in a high degree of divergence enabling the formation of the final products in just 10 or 11 steps each with a minimum of overall synthetic effort. Chiral pool starting materials (l-malic acid, threonines) were employed for the outer building blocks while the middle building blocks were accessed by diastereo- and enantioselective methods. A highlight of this work consists in the straightforward preparation of epimeric hydroxyazetidine amino acids, useful building blocks on their own, enabling the first synthesis of 3’’-hydroxymugineic acid and 3’’-hydroxy-2’-deoxymugineic acid.

Design, synthesis, and evaluation of compounds capable of reducing Pseudomonas aeruginosa virulence

Anti-virulence approaches in the treatment of Pseudomonas aeruginosa (PA)-induced infections have shown clinical potential in multiple in vitro and in vivo studies. However, development of these compounds is limited by several factors, including the lack of molecules capable of penetrating the membrane of gram-negative organisms. Here, we report the identification of novel structurally diverse compounds that inhibit PqsR and LasR-based signaling and diminish virulence factor production and biofilm growth in two clinically relevant strains of P. aeruginosa. It is the first report where potential anti-virulent agents were evaluated for inhibition of several virulence factors of PA. Finally, co-treatment with these inhibitors significantly reduced the production of virulence factors induced by the presence of sub-inhibitory levels of ciprofloxacin. Further, we have analyzed the drug-likeness profile of designed compounds using quantitative estimates of drug-likeness (QED) and confirmed their potential as hit molecules for further development.

Synthesis of new chalcone-based homoserine lactones and their antiproliferative activity evaluation

Three series of new homoserine lactone analogs were efficiently synthesized starting from methionine and further evaluated for their antiproliferative activity against different cancer cell lines. Among these compounds, some of the chalcone containing compounds 6a-n showed acceptable antiproliferative activity against prostate cancer cells DU145 and PC-3 with the IC50 values less than 10 μM. Compounds 6c, 6e and 6h inhibited growth of DU145 and PC-3 cells at low micromolar levels with the IC50 values ranging from 3.0 to 5.0 μM, much more potent than natural OdDHL. Compound 6e concentration-dependently inhibited colony formation and cell migration of DU145 cells. A synergistic effect on the growth inhibition and the apoptosis of DU145 cells was observed when compound 6e was used in combination with TRAIL. OdDHL or 6e treatment concentration-dependently activated TRAIL death receptor DR5 which may account for the observed synergistic effect of 6e or OdDHL with TRAIL on the growth inhibition and cell apoptosis. Compound 6e also inhibited migration of DU145 cells in a time- and concentration-dependent manner. The data suggest that quorum sensing molecules OdDHL and 6e may improve the sensitivity of DU145 cells toward TRAIL via activating DR5, compound 6e may be used as a potential lead compound for developing new TRAIL receptor agonists.

Synthesis and biological evaluation of novel L-homoserine lactone analogs as quorum sensing inhibitors of pseudomonas aeruginosa

In this study, we synthesized four series of novel L-homoserine lactone analogs and evaluated their in vitro quorum sensing (QS) inhibitory activity against two biomonitor strains, Chromobacterium violaceum CV026 and Pseudomonas aeruginosa PAO1. Studies of the structure–activity relationships of the set of L-homoserine lactone analogs indicated that phenylurea-containing N-dithiocarbamated homoserine lactones are more potent than (Z)-4-bromo-5-(bromomethylene)-2(5H)-furanone (C30), a positive control for biofilm formation. In particular, compared with C30, QS inhibitor 11f significantly reduced the production of virulence factors (pyocyanin, elastase and rhamnolipid), swarming motility, the formation of biofilm and the mRNA level of QS-related genes regulated by the QS system of PAO1. These results reveal 11f as a potential lead compound for developing novel antibacterial quorum sensing inhibitors.

A cogeneration process for producing sulfur and sulfur on behalf of acetate acid diester method (by machine translation)

The invention technical field of chemical synthesis, in particular relates to a methionine as raw material production process for producing sulfur and sulfur on behalf of acetate acid diester method. The invention states the payment proportional to production for preparing sulfur and sulfur on behalf of acetate acid diester method, in order to methionine and halogenated acetic acid as the raw material, the preparation comprising a homoserine lactone hydrohalide salt (IV), a sulfur acetate (I) and sulfur on behalf of the b b acid diester (II) of the three kinds of chemical products, and each between the products easy to separate and purify. (by machine translation)

Preparation method of high-optical-purity D- or L-selenomethionine

The invention discloses a preparation method of high-optical-purity D- or L-selenomethionine. The preparation method comprises the following steps: by taking D- or L-methionine as initial raw materials and diethyl sulfate or halogenated alkyl acid or derived esters as alkylation reagents, generating sulfonium salt, desulfurizing and closing ring under acidic conditions, to produce alpha-amino-gama-butyrolactone halate, having addition reaction to alpha-amino-gama-butyrolactone halate with methyl selenol salt and opening ring, acidifying with organic acid, and recrystallizing to obtain D- or L-selenomethionine. The chemical purity of the product is more than or equal to 99%, and the high optical purity is more than or equal to 99%. The preparation method is low-cost and easily available in raw materials, simple in steps and easy to operate, simple in reaction conditions, and suitable for large-scale production.

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.

Method for synthesizing L-glufosinate-ammonium intermediate (S)-3-amino-gamma-butyrolactone hydrochloride, and application of method

The invention relates and belongs to the field of pesticide chemistry, and in particular relates to a method for synthesizing L-glufosinate-ammonium intermediate (S)-3-amino-gamma-butyrolactone hydrochloride, and application of the method. The method takes L-methionine, concentrated hydrochloric acid and chloroacetic acid or bromoacetic acid as raw materials, and the L-glufosinate-ammonium intermediate (S)-3-amino-gamma-butyrolactone hydrochloride is obtained by a one-pot reaction. The method is simple in operation process and purification process, and high in yield; after the method is adopted, the production cost of L-glufosinate-ammonium is remarkably lowered.

Refined glufosinate preparation method

The invention discloses a refined glufosinate preparation method. The refined glufosinate preparation method comprises the steps that 1, L-methionine and alpha-halogenated carboxylic acid or its derivative react under the effect of a phase transfer catalyst to obtain L-homoserine lactone hydrogen halide salt; 2, the L-homoserine lactone hydrogen halide salt and an amino protective reagent react to obtain a compound IV; 3, the compound IV performs ring-opening reaction with dihalogen sulfoxide, phosgene, triphosgene (BTC) or trimethyl halogenosilane to obtain a compound V, and the compound V is subjected to subsequent reaction treatment to obtain refined glufosinate, wherein the phase transfer catalyst is a quaternary ammonium salt phase transfer catalyst. The preparation method greatly improves the yield of the refined glufosinate, intermediate products revolved in reaction are easy to detect, the conditions are mild, and the refined glufosinate preparation method is suitable for industrial production.