167896-48-2Relevant articles and documents
Rapid Broad Spectrum Detection of Carbapenemases with a Dual Fluorogenic-Colorimetric Probe
Ma, Chi-Wang,Ng, Kenneth King-Hei,Yam, Bill Hin-Cheung,Ho, Pak-Leung,Kao, Richard Yi-Tsun,Yang, Dan
supporting information, p. 6886 - 6894 (2021/05/29)
Carbapenems stand as one of the last-resort antibiotics; however, their efficacy is threatened by the rising number and rapid spread of carbapenemases. Effective antimicrobial stewardship thus calls for rapid tests for these enzymes to aid appropriate prescription and infection control. Herein, we report the first effective pan-carbapenemase reporter CARBA-H with a broad scope covering all three Ambler classes. Using a chemical biology approach, we demonstrated that the absence of the 1β-substituent in the carbapenem core is key to pan-carbapenemase recognition, which led to our rational design and probe development. CARBA-H provides a dual colorimetric-fluorogenic response upon carbapenemase-mediated hydrolysis. A clear visual readout can be obtained within 15 min when tested against a panel of carbapenemase-producing Enterobacteriaceae (CPE) clinical isolates that notably includes OXA-48 and OXA-181-producing strains. Furthermore, CARBA-H can be applied to the detection of carbapemenase activity in CPE-spiked urine samples.
BETA-LACTAM COMPOUNDS AND METHODS OF USE THEREOF
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Page/Page column 47; 49; 50, (2020/04/25)
Beta-lactam compounds to detect carbapenemases or microbial carbapenem resistance are disclosed. The compounds contain a chemical probe. Upon hydrolysis by carbapenemases, the compounds undergo intramolecular rearrangement and release the chemical probe. Detection of the released chemical probe indicates the presence of carbapenemases and the presence of microbial carbapenem resistance.
Enantioselective Synthesis of cis- A nd trans-Borocyclopropylmethanol: Simple Building Blocks to Access Heterocycle-Substituted Cyclopropylmethanols
Charette, André B.,Navuluri, Chandrasekhar,Siddiqui, Saher H.
, p. 3834 - 3846 (2019/10/11)
An enantioselective and non-oxidative methodology was developed to obtain enantioenriched cyclopropyl boronates using a diethanolamine-promoted selective decomplexation of dioxaborolane. The non-oxidative decomplexation of the dioxaborolane ligand from the cyclopropylmethoxide species formed in the dioxaborolane-mediated Simmons-Smith cyclopropanation reaction provided the enantio?-enriched CIDA-based (CIDA = N-cyclohexyliminodiacetic acid) boro?-cyclopropane in 92% yield and 95.6:4.4 er. A robustness screen has shown diethanolamine to be compatible with esters, carbamates and N-heterocycles, providing a tool to access enantioenriched cyclopropanes carrying not only base-sensitive but oxidizable functional groups as well. Diethanolamine was found to be compatible with the modified zinco-cyclopropanation reaction of allyl alcohol to remove residual dioxaborolane from the corresponding cis-N-heterocycle cyclopropylmethanol, thereby leading to improved yields.
Enantioselective α-Allylation of Acyclic Esters Using B(pin)-Substituted Electrophiles: Independent Regulation of Stereocontrol Elements through Cooperative Pd/Lewis Base Catalysis
Scaggs, W. Rush,Snaddon, Thomas N.
, p. 14378 - 14381 (2018/09/21)
Cooperation between a Lewis base and Pd catalyst enables the direct enantioselective α-functionalization of aryl and vinyl acetic acid esters using a bifunctional B(pin)-substituted electrophile. Critical to the success of this method was the recognition that both catalysts could control the necessary stereochemical aspects; the Lewis base catalyst controls the enantioselectivity of the reaction, whereas the Pd catalyst regulates alkenyl-B(pin) configuration. This is the first example of using cooperative catalysis to control both stereochemical features during Pd-catalyzed allylic alkylation.
Synthesis of Alkenyl Boronates from Epoxides with Di-[B(pin)]-methane via Pd-Catalyzed Dehydroboration
Murray, Stephanie A.,Luc, Eugenia C. M.,Meek, Simon J.
supporting information, p. 469 - 472 (2018/01/28)
A practical and broadly applicable catalytic method for the synthesis of (E)-alkenylborons is presented. Reactions are promoted by [Pd(Cl)(η3-C3H5)]2 and proceed by the dehydroboration of cyclic borates. Through
Ratiometric electrochemical detection of hydrogen peroxide and glucose
Goggins, Sean,Apsey, Ellen A.,Mahon, Mary F.,Frost, Christopher G.
supporting information, p. 2459 - 2466 (2017/03/20)
Hydrogen peroxide (H2O2) detection is of high importance as it is a versatile (bio)marker whose detection can indicate the presence of explosives, enzyme activity and cell signalling pathways. Herein, we demonstrate the rapid and accurate ratiometric electrochemical detection of H2O2 using disposable screen-printed electrodes through a reaction-based indicator assay. Ferrocene derivatives equipped with self-immolative linkers and boronic acid ester moieties were synthesised and tested, and, through a thorough assay optimisation, the optimum probe showed good stability, sensitivity and selectivity towards H2O2. The optimised conditions were then applied to the indirect detection of glucose via an enzymatic assay, capable of distinguishing 10 μM from the background within minutes.
Highly selective methods for synthesis of internal (α-) vinylboronates through efficient NHC-Cu-catalyzed hydroboration of terminal alkynes. Utility in chemical synthesis and mechanistic basis for selectivity
Jang, Hwanjong,Zhugralin, Adil R.,Lee, Yunmi,Hoveyda, Amir H.
, p. 7859 - 7871 (2011/06/27)
Cu-catalyzed methods for site-selective hydroboration of terminal alkynes, where the internal or α-vinylboronate is generated predominantly (up to >98%) are presented. Reactions are catalyzed by 1-5 mol % of N-heterocyclic carbene (NHC) complexes of copper, easily prepared from N-aryl-substituted commercially available imidazolinium salts, and proceed in the presence of commercially available bis(pinacolato)diboron [B2(pin)2] and 1.1 equiv of MeOH at -50 to -15 °C in 3-24 h. Propargyl alcohol and amine and the derived benzyl, tert-butyl, or silyl ethers as well as various amides are particularly effective substrates; also suitable are a wide range of aryl-substituted terminal alkynes, where higher α-selectivity is achieved with substrates that bear an electron-withdrawing substituent. α-Selective Cu-catalyzed hydroborations are amenable to gram-scale procedures (1 mol % catalyst loading). Mechanistic studies are presented, indicating that α selectivity arises from the structural and electronic attributes of the NHC ligands and the alkyne substrates. Consistent with suggested hypotheses, catalytic reactions with a Cu complex, derived from an N-adamantyl-substituted imidazolinium salt, afford high β selectivity with the same class of substrates and under similar conditions.
SN2′ boron-mediated Mitsunobu reactions - A new one-pot three-component synthesis of substituted enamides and enol benzoates
Berree, Fabienne,Gernigon, Nicolas,Hercouet, Alain,Chia, Hui Lin,Carboni, Bertrand
supporting information; experimental part, p. 329 - 333 (2009/07/04)
The conversion of (3-hydroxy-1-propen-1-yl)boronates to substituted enamides and enol benzoates is readily achieved in a one-pot procedure consisting of a regiocontrolled Mitsunobu reaction with convenient nucleophiles, followed by allylboration of aldehydes. Wiley-VCH Verlag GmbH & Co. KGaA, 2009.
A convenient catalyst for aqueous and protein Suzuki-Miyaura cross-coupling
Chalker, Justin M.,Wood, Charlotte S. C.,Davis, Benjamin G.
supporting information; experimental part, p. 16346 - 16347 (2010/01/29)
(Figure Presented) A phosphine-free palladium catalyst for aqueous Suzuki-Miyaura cross-coupling is presented. The catalyst is active enough to mediate hindered, ortho-substituted biaryl couplings but mild enough for use on peptides and proteins. The Suzuki-Miyaura couplings on protein substrates are the first to proceed in useful conversions. Notably, hydrophobic aryl and vinyl groups can be transferred to the protein surface without the aid of organic solvent since the aryl- and vinylboronic acids used in the coupling are water-soluble as borate salts. The convenience and activity of this catalyst prompts use in both general synthesis and bioconjugation.
Development of an end-game strategy towards apoptolidin: A sequential Suzuki coupling approach
Jin, Bohan,Liu, Qingsong,Sulikowski, Gary A.
, p. 401 - 408 (2007/10/03)
An end-game strategy towards the synthesis of apoptolidin has been demonstrated in a model study, in which the C(1)-C(15) fragment was successfully assembled using three consecutive Suzuki coupling reactions.
