1082207-52-0Relevant academic research and scientific papers
Discovery of Mechanism-Based Inactivators for Human Pancreatic Carboxypeptidase A from a Focused Synthetic Library
Testero, Sebastián A.,Granados, Carla,Fernández, Daniel,Gallego, Pablo,Covaleda, Giovanni,Reverter, David,Vendrell, Josep,Avilés, Francesc X.,Pallarès, Irantzu,Mobashery, Shahriar
, p. 1122 - 1127 (2017)
Metallocarboxypeptidases (MCPs) are involved in many biological processes such as fibrinolysis or inflammation, development, Alzheimer's disease, and various types of cancer. We describe the synthesis and kinetic characterization of a focused library of 22 thiirane- and oxirane-based potential mechanism-based inhibitors, which led to discovery of an inhibitor for the human pro-carboxypeptidase A1. Our structural analyses show that the thiirane-based small-molecule inhibitor penetrates the barrier of the pro-domain to bind within the active site. This binding leads to a chemical reaction that covalently modifies the catalytic Glu270. These results highlight the importance of combined structural, biophysical, and biochemical evaluation of inhibitors in design strategies for the development of spectroscopically nonsilent probes as effective beacons for in vitro, in cellulo, and/or in vivo localization in clinical and industrial applications.
Highly Regioselective Palladium-Catalyzed Carboxylation of Allylic Alcohols with CO2
Mita, Tsuyoshi,Higuchi, Yuki,Sato, Yoshihiro
, p. 16391 - 16394 (2015/11/09)
Various allylic alcohols were carboxylated in the presence of a catalytic amount of PdCl2 and PPh3 using ZnEt2 as a stoichiometric transmetalation agent under a CO2 atmosphere (1atm). This carboxylation proceeded in a highly regioselective manner to afford branched carboxylic acids predominantly. The β,γ-unsaturated carboxylic acid thus obtained was successfully converted into an optically active γ-butyrolactone, a known intermediate of (R)-baclofen.
Use of formate salts as a hydride and a Co2 source in PGeP -palladium complex-catalyzed hydrocarboxylation of allenes
Zhu, Chuan,Takaya, Jun,Iwasawa, Nobuharu
supporting information, p. 1814 - 1817 (2015/04/14)
Use of formate salts as a hydride as well as a CO2 source was achieved in a PGeP-palladium complex-catalyzed hydrocarboxylation of allenes through a highly efficient decarboxylation-carboxylation process. This reaction proceeds under mild conditions and provides an alternative strategy for utilizing formate salts as a C1 source.
Hydrocarboxylation of allenes with CO2 catalyzed by silyl pincer-type palladium complex
Takaya, Jun,Iwasawa, Nobuharu
supporting information; experimental part, p. 15254 - 15255 (2009/03/12)
Tridentate PSiP pincer-type palladium complex-catalyzed hydrocarboxylation of allenes under carbon dioxide to give synthetically useful β,γ-unsaturated carboxylic acids was developed. This novel CO2-fixation reaction is thought to proceed through the catalytic generation of σ-allyl palladium species via hydropalladation of allenes, followed by its regioselective nucleophilic addition to CO2 in the presence of an appropriate reducing agent. The reaction is successfully applied to various allenes bearing functional groups such as ester, carbamate, ketone, and alkene, showing high synthetic utility of this protocol. Copyright
