@article{huang_tang_yu_sanyal_jia_liu_guo_chang_2018, title={Mechanistic Investigation of Oxidative Decarboxylation Catalyzed by Two Iron(II)- and 2-Oxoglutarate-Dependent Enzymes}, volume={57}, ISSN={["0006-2960"]}, url={http://www.scopus.com/inward/record.url?eid=2-s2.0-85044655678&partnerID=MN8TOARS}, DOI={10.1021/acs.biochem.8b00115}, abstractNote={Two non-heme iron enzymes, IsnB and AmbI3, catalyze a novel decarboxylation-assisted olefination to produce indole vinyl isonitrile, an important building block for many natural products. Compared to other reactions catalyzed by this enzyme family, decarboxylation-assisted olefination represents an attractive biosynthetic route and a mechanistically unexplored pathway in constructing a C═C bond. Using mechanistic probes, transient state kinetics, reactive intermediate trapping, spectroscopic characterizations, and product analysis, we propose that both IsnB and AmbI3 initiate stereoselective olefination via a benzylic C-H bond activation by an Fe(IV)-oxo intermediate, and the reaction likely proceeds through a radical- or carbocation-induced decarboxylation to complete C═C bond installation.}, number={12}, journal={BIOCHEMISTRY}, author={Huang, Jhih-Liang and Tang, Yijie and Yu, Cheng-Ping and Sanyal, Dev and Jia, Xinglin and Liu, Xinyu and Guo, Yisong and Chang, Wei-chen}, year={2018}, month={Mar}, pages={1838–1841} } @article{chang_sanyal_huang_ittiamornkui_zhu_liu_2017, title={In Vitro Stepwise Reconstitution of Amino Acid Derived Vinyl Isocyanide Biosynthesis: Detection of an Elusive Intermediate}, volume={19}, ISSN={["1523-7052"]}, url={http://www.scopus.com/inward/record.url?eid=2-s2.0-85014520010&partnerID=MN8TOARS}, DOI={10.1021/acs.orglett.7b00258}, abstractNote={In vitro reconstitution of a newly discovered isonitrile synthase (AmbI1 and AmbI2) and the detection of an elusive intermediate (S)-3-(1H-indol-3-yl)-2-isocyanopropanoic acid 1 in indolyl vinyl isocyanide biogenesis are reported. The characterization of iron/2-oxoglutarate (Fe/2OG) dependent desaturases IsnB and AmbI3 sheds light on the possible mechanism underlying stereoselective alkene installation to complete the biosynthesis of (E)- and (Z)-3-(2-isocyanovinyl)-1H-indole 2 and 5. Establishment of a tractable isonitrile synthase system (AmbI1 and AmbI2) paves the way to elucidate the enigmatic enzyme mechanism for isocyanide formation.}, number={5}, journal={ORGANIC LETTERS}, author={Chang, Wei-Chen and Sanyal, Dev and Huang, Jhih-Liang and Ittiamornkui, Kuljira and Zhu, Qin and Liu, Xinyu}, year={2017}, month={Mar}, pages={1208–1211} }