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Chemo‐Enzymatic Synthesis of Pyrazines and Pyrroles
Author(s) -
Xu Jin,
Green Anthony P.,
Turner Nicholas J.
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201810555
Subject(s) - chemistry , amination , amine gas treating , pyrrole , ketone , reductive amination , transaminase , organic chemistry , catalysis , combinatorial chemistry , enzyme
Abstract Herein we report the biocatalytic synthesis of substituted pyrazines and pyrroles using a transaminase (ATA) to mediate the key amination step of the ketone precursors. Treatment of α‐diketones with ATA‐113 in the presence of a suitable amine donor yielded the corresponding α‐amino ketones which underwent oxidative dimerization to the pyrazines. Selective amination of α‐diketones in the presence of β‐keto esters afforded substituted pyrroles in a biocatalytic equivalent of the classical Knorr pyrrole synthesis. Finally we have shown that pyrroles can be prepared by internal amine transfer catalyzed by a transaminase in which no external amine donor is required.