141971-69-9Relevant academic research and scientific papers
Nickel-Catalyzed Reversible Functional Group Metathesis between Aryl Nitriles and Aryl Thioethers
Delcaillau, Tristan,Boehm, Philip,Morandi, Bill
supporting information, p. 3723 - 3728 (2021/04/07)
We describe a new functional group metathesis between aryl nitriles and aryl thioethers. The catalytic system nickel/dcype is essential to achieve this fully reversible transformation in good to excellent yields. Furthermore, the cyanide- and thiol-free reaction shows high functional group tolerance and great efficiency for the late-stage derivatization of commercial molecules. Finally, synthetic applications demonstrate its versatility and utility in multistep synthesis.
Total synthesis of human hepcidin through regioselective disulfide-bond formation by using the safety-catch cysteine protecting group 4,4′-dimethylsulfinylbenzhydryl
Dekan, Zoltan,Mobli, Mehdi,Pennington, Michael W.,Fung, Eileen,Nemeth, Elizabeta,Alewood, Paul F.
, p. 2931 - 2934 (2014/04/03)
A safety-catch cysteine protecting group, S-4,4′- dimethylsulfinylbenzhydryl (Msbh), was designed and developed to expand the capabilities of synthetic strategies for the regioselective formation of disulfide bonds in cysteine-rich peptides. The directed regioselective synthesis of human hepcidin, which contains four disulfide bonds, was undertaken and led to a high-resolution NMR structure under more physiologically relevant conditions than previously. Conversely, hepcidin synthesized with the formerly assigned vicinal disulfide-bond connectivity displayed significant conformational heterogeneity under similar conditions. The two synthetic forms of human hepcidin induced ferroportin internalization with apparent EC 50 values of 2.0 (native fold, 1) and 4.4 nM (non-native fold, 2), with 2 undergoing isomerization to 1 in the presence of ferroportin expressing cells.
6-azabicyclo[3.2.1]octanes via copper-catalyzed enantioselective alkene carboamination
Casavant, Barbara J.,Hosseini, Azade S.,Chemler, Sherry R.
supporting information, p. 2697 - 2702 (2014/09/29)
Bridged bicyclic rings containing nitrogen heterocycles are important motifs in bioactive small organic molecules. An enantioselective copper-catalyzed alkene carboamination reaction that creates bridged heterocycles is reported herein. Two new rings are
Silicon ring strain creates high-conductance pathways in single-molecule circuits
Su, Timothy A.,Widawsky, Jonathan R.,Li, Haixing,Klausen, Rebekka S.,Leighton, James L.,Steigerwald, Michael L.,Venkataraman, Latha,Nuckolls, Colin
supporting information, p. 18331 - 18334 (2014/01/06)
Here we demonstrate for the first time that strained silanes couple directly to gold electrodes in break-junction conductance measurements. We find that strained silicon molecular wires terminated by alkyl sulfide aurophiles behave effectively as single-molecule parallel circuits with competing sulfur-to-sulfur (low G) and sulfur-to-silacycle (high G) pathways. We can switch off the high conducting sulfur-to-silacycle pathway by altering the environment of the electrode surface to disable the Au-silacycle coupling. Additionally, we can switch between conductive pathways in a single molecular junction by modulating the tip-substrate electrode distance. This study provides a new molecular design to control electronics in silicon-based single molecule wires.
"SAFETY-CATCH" PROTECTING GROUPS IN PEPTIDE SYNTHESIS
Patek, Marcel,Lebl, Michal
, p. 508 - 524 (2007/10/02)
A new benzhydryl-type protective groups for amides based on the concept of converting a stable protecting group into a labile one (safety-catch principle) are described.The p-substituted benzhydrylamine derivatives III(a, b), IV(a, b) are shown to be labi
