The (beta-chloro-, (beta, beta-dichloro-, and (beta, beta, beta-trichloro-alpha-aminoethyl)phosphonic acids have been synthesized and their inhibitory properties on the alanine racemases [EC 5.1.1.1] and the D-Ala:D-Ala ligases [EC 6.3.2.4] from Pseudomonas aeruginosa and Streptococcus faecalis have been evaluated. The monochloro and the dichloro derivatives of Ala-P exhibit a strong inhibition on the racemases of the two species tested but do not behave as suicide substrates. Only the D-Ala:D-Ala ligase of S. faecalis is inhibited by these compounds. The poor antibacterial activity observed with beta-chloro- and beta, beta-dichloro-Ala-P might be enhanced by the peptide-transport strategy.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/jm00151a024 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Iridium-catalyzed reductive β-alkylation of (iso)quinoline derivatives by an enone-trapping strategy.
Org Biomol Chem
June 2024
Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Wushan Rd-381, Guangzhou 510641, People's Republic of China.
By employing [IrCp*Cl]/Mg(OMe)/(CHO) as an applicable catalyst system, we report a reductive β-alkylation of (iso)quinolinium salts with cost-effective and readily available β-chloro ketones, proceeding with good chemoselectivity, mild reaction conditions, and without the need for introduction of a substituent at position-3 of the quinolyl skeleton. Mechanistic investigations suggest that the reaction proceeds a sequence of hydride transfer-initiated dearomatization of (iso)quinolinium salts, enamine-trapping of enone and a second round of hydride transfer to the coupling adducts. The present work offers an important complement to the synthesis of functionalized (iso)tetrahydroquinolines.
View Article and Find Full Text PDFElectrochemical Vicinal C-H Difunctionalization of Saturated Azaheterocycles.
J Am Chem Soc
January 2024
Department of Chemistry and Chemical Biology, Cornell University, Ithaca, New York 14853, United States.
A method to functionalize two vicinal C-H bonds of saturated azaheterocycles is described. The procedure involves subjecting the substrate to a mixture of hydrochloric acid, acetic acid, and acetic anhydride in an undivided electrochemical cell at a constant current, resulting in stereoselective conversion to the corresponding α-acetoxy-β-chloro derivative. The α-position can be readily substituted with a range of other groups, including alkyl, aryl, allyl, alkynyl, alkoxy, or azido functionalities.
View Article and Find Full Text PDFDevelopment of a Chemogenetic Approach to Manipulate Intracellular pH.
J Am Chem Soc
June 2023
Regenerative and Restorative Medicine Research Center (REMER), Research Institute for Health Sciences and Technologies (SABITA), Istanbul Medipol University, Istanbul 34810, Türkiye.
Chemogenetic Operation of iNTRacellular prOton Levels (pH-Control) is a novel substrate-based enzymatic method that enables precise spatiotemporal control of ultralocal acidification in cultured cell lines and primary neurons. The genetically encoded biosensor SypHer3s showed that pH-Control effectively acidifies cytosolic, mitochondrial, and nuclear pH exclusively in the presence of β-chloro-d-alanine in living cells in a concentration-dependent manner. The pH-Control approach is promising for investigating the ultralocal pH imbalance associated with many diseases.
View Article and Find Full Text PDFSynthesis of ()-β-Chloro-enamides via a Base-Promoted -Hydroamidation of Alkynyl Chlorides Using 1,1-Dichloroalkenes as Precursor.
J Org Chem
July 2022
National Research Center for Carbohydrate Synthesis and Key Laboratory of Chemical Biology, College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330022, P. R. China.
An efficient and general base-promoted reaction of 1,1-dichloroalkenes with secondary sulfonamides and amides for the synthesis of ()-β-chloro-enamides has been described. This reaction exhibits functional group tolerance under simple and mild conditions. Mechanistic study indicated that a stereoselective -hydroamidation of alkynyl chlorides generated from 1,1-dichloroalkenes was the key step.
View Article and Find Full Text PDFRing-Expansion Reactions of Epoxy Amides and Enamides: Functionalized Azetidines, Dihydrofurans, Diazocanes, or Dioxa-3-azabicyclonon-4-enes?
J Org Chem
May 2022
School of Chemistry, University of Hyderabad, Hyderabad, Telangana 500 046, India.
Functionalized azetidines, 2,3-dihydrofurans, or the unorthodox dioxa-3-azabicyclonone-4-ene motifs are the products from transition metal-free reaction between -oxiranylmethyl benzenesulfonamide and β-chloro-cinnamaldehyde, depending on whether one uses either NaI/KCO or LiBr/KCO. These ring expansion reactions involve enamide (X-ray evidence) derived from -oxiranylmethyl benzenesulfonamide and β-chloro-cinnamaldehyde as an intermediate. The -oxiranylmethyl benzenesulfonamide itself upon heating gives readily separable and crystalline isomeric diazocanes that can be characterized by X-ray crystallography.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!