105535-09-9Relevant articles and documents
Mechanistic studies of an antibody-catalyzed elimination reaction
Romesberg, Floyd E.,Flanagan, Mark E.,Uno, Tetsuo,Schultz, Peter G.
, p. 5160 - 5167 (1998)
Catalytic antibody 43D4-3D12, which was generated against the substituted tertiary amine 1, catalyzes the elimination of HF from β- fluoroketone 2. We have cloned and produced the antibody as a chimeric Fab and constructed a model of the active site-substrate complex. Mutagenesis studies of the active site indicate that Glu(H)50 acts as the general base and suggest that Tyr96(L) may also play a role in the elimination reaction. Antibody 43D4-3D12 also efficiently catalyzes the elimination of HBr from substrate 4 by an E2 mechanism, again involving selective abstraction of the proton β-to the nitrophenyl ring by Glu(H)50. The antibody-catalyzed reaction affords predominantly the internal olefins, whereas the major product resulting from the uncatalyzed reaction is the alcohol, which arises from the competing substitution reaction. In addition, antibody 43D43D12 catalyzes an acetal hydrolysis reaction in which Glu(H)50 likely acts as a general acid. These studies point to the Success of this particular hapten design strategy in generating an active site with a desired catalytic functional group. They also illustrate the utility of using related reactions as mechanistic probes of biological catalysis.
Visible-Light-Mediated Reactions of Electrophilic Radicals with Vinyl and Allyl Trifluoroborates
Fernandez Reina, Daniel,Ruffoni, Alessandro,Al-Faiyz, Yasair S. S.,Douglas, James J.,Sheikh, Nadeem S.,Leonori, Daniele
, p. 4126 - 4130 (2017/06/19)
Visible-light photoredox catalysis enables the vinylation and allylation of electrophilic radicals with readily available potassium trifluoroborate reagents. The processes show good functional group compatibility, and mechanistic and computational studies
Amine-Activated Iron Catalysis: Air- and Moisture-Stable Alkene and Alkyne Hydrofunctionalization
Challinor, Amy J.,Calin, Marc,Nichol, Gary S.,Carter, Neil B.,Thomas, Stephen P.
supporting information, p. 2404 - 2409 (2016/08/16)
A simple alkylamine [(iPr)2NEt] has been used to activate an air- and moisture-stable iron(II) pre-catalyst for alkene and alkyne hydrofunctionalization reactions. This amine activation has enabled the highly operationally simple hydrosilylatio