383145-89-9Relevant academic research and scientific papers
Syntheses of 4-, 5-, 6-, and 7-substituted tryptamine derivatives and the use of a bromine atom as a protecting group
René, Olivier,Fauber, Benjamin P.
supporting information, p. 830 - 833 (2014/02/14)
Orthogonal syntheses of 4-, 5-, 6-, and 7-chloro substituted tryptamine derivatives were performed under the Grandberg-Zuyanova-modified Fisher indole-synthesis conditions. In the 4- and 6-substituted tryptamine cases, a bromine atom was utilized as an easily cleavable protecting group, which allowed complete regiocontrol. In addition, a chlorine substituent was preserved in the debromination step and could be utilized as a synthetic handle for late-stage diversification under modern Pd(0) catalysis conditions.
Regioselective arene halogenation using the FAD-dependent halogenase RebH
Payne, James T.,Andorfer, Mary C.,Lewis, Jared C.
supporting information, p. 5271 - 5274 (2013/06/26)
Together we're strong: Co-expression of the halogenase RebH with GroEL/ES and fusion of the flavin reductase RebF to MBP enabled production of both enzymes on scales sufficient for preparative regioselective oxidative halogenation of arenes. The activity and selectivity of RebH contrasts with those reported for the structurally homologous halogenase PrnA, which only enabled halogenation of nonnatural substrates at their most electronically activated positions. Copyright
