A highly efficient and mild transamidation of amides with amines co-catalysed by borinic acid and acetic acid has been reported. A wide range of functionalised formamides was synthesized in excellent yields, including important chiral α-amino acid derivatives, with minor racemisation being observed. Experiments suggested that the reaction rely on a cooperative catalysis involving an enhanced boron-derived Lewis acidity rather than an improved Brønsted acidity of acetic acid.
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http://dx.doi.org/10.1002/chem.201600234 | DOI Listing |
Chemistry
December 2024
Institut des Sciences Moléculaires, UMR 5255, Université de Bordeaux, CNRS, Bordeaux INP, 351 Cours de la libération, 33405, Talence cedex, France.
Various protecting groups have been developed for boronic acids, mostly based on diols. Alternatives include trifluoroborates and amine complexes, which offer easier synthesis and release under milder conditions. We present here a new strategy involving photocleavable protecting groups for boronic and borinic acids, based on the 2-nitrobenzyl motif.
View Article and Find Full Text PDFAntimicrob Agents Chemother
November 2024
Servicio de Microbiología Clínica e Instituto de Investigación Biomédica A Coruña (INIBIC), Complexo Hospitalario Universitario A Coruña, A Coruña, Spain.
J Med Chem
October 2024
IBMM, University of Montpellier, CNRS, ENSCM, 34293 Montpellier, France.
The benzoxaborinine scaffold, a homologue of benzoxaborole with an additional carbon atom in the boracycle, shows significant potential in developing new therapeutic agents. This study reports the synthesis, inhibition assays against four human carbonic anhydrase (hCA, EC 4.2.
View Article and Find Full Text PDFMicrobiol Spectr
November 2024
Research Service, Veterans Affairs Northeast Ohio Healthcare System, Cleveland, Ohio, USA.
Taniborbactam (formerly VNRX-5133) is a novel, investigational boronic acid β-lactamase inhibitor. The combination of cefepime (FEP) with taniborbactam is active against carrying class A, B, C, and/or D enzymes. We assessed the activity of FEP-taniborbactam against clinical strains carrying ( = 50, 100%), of which 78% harbored at least one extended-spectrum β-lactamase (ESBL).
View Article and Find Full Text PDFJ Antimicrob Chemother
December 2024
IHMA, Schaumburg, IL, USA.
Objectives: Taniborbactam is a boronate-based β-lactamase inhibitor in clinical development in combination with cefepime.
Methods: Cefepime-taniborbactam and comparator broth microdilution MICs were determined for patient isolates of Enterobacterales (n = 20 725) and Pseudomonas aeruginosa (n = 7919) collected in 59 countries from 2018 to 2022. Taniborbactam was tested at a fixed concentration of 4 mg/L.
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