147091-70-1Relevant academic research and scientific papers
Repurposing Nonheme Iron Hydroxylases to Enable Catalytic Nitrile Installation through an Azido Group Assistance
Davidson, Madison,McNamee, Meredith,Fan, Ruixi,Guo, Yisong,Chang, Wei-Chen
, p. 3419 - 3423 (2019)
Three mononuclear nonheme iron and 2-oxoglutarate dependent enzymes, l-Ile 4-hydroxylase, l-Leu 5-hydroxylase and polyoxin dihydroxylase, are previously reported to catalyze the hydroxylation of l-isoleucine, l-leucine, and l-α-amino-δ-carbamoylhydroxyvaleric acid (ACV). In this study, we showed that these enzymes can accommodate leucine isomers and catalyze regiospecific hydroxylation. On the basis of these results, as a proof-of-concept, we demonstrated that the outcome of the reaction can be redirected by installation of an assisting group within the substrate. Specifically, instead of canonical hydroxylation, these enzymes can catalyze non-native nitrile group installation when an azido group is introduced. The reaction is likely to proceed through C - H bond activation by an Fe(IV)-oxo species, followed by azido-directed C-N bond formation. These results offer a unique opportunity to investigate and expand the reaction repertoire of Fe/2OG enzymes.
Acceptor-Controlled Transfer Dehydration of Amides to Nitriles
Okabe, Hiroyuki,Naraoka, Asuka,Isogawa, Takahiro,Oishi, Shunsuke,Naka, Hiroshi
supporting information, p. 4767 - 4770 (2019/06/17)
Palladium-catalyzed dehydration of primary amides to nitriles efficiently proceeds under mild, aqueous conditions via the use of dichloroacetonitrile as a water acceptor. A key to the design of this transfer dehydration catalysis is the identification of an efficient water acceptor, dichloroacetonitrile, that preferentially reacts with amides over other polar functional groups with the aid of the Pd catalyst and makes the desired scheme exergonic, thereby driving the dehydration.
Synthesis of a key precursor for orienticin C and model study on ruthenium-mediated macrocyclization
Pearson, Anthony J.,Ciurea, Diana V.
, p. 760 - 763 (2008/09/18)
(Chemical Equation Presented) A tripeptido-arene-ruthenium complex was prepared as a key precursor for the projected synthesis of orienticin C, demonstrating that the cyclopentadienylruthenium moiety can be attached to a chloroarene in the presence of mul
