In Vitro Stepwise Reconstitution of Amino Acid Derived Vinyl Isocyanide Biosynthesis: Detection of an Elusive Intermediate

Wei-Chen Chang; Dev Sanyal; Jhih-Liang Huang; Kuljira Ittiamornkul; Qin Zhu; Xinyu Liu

doi:10.1021/acs.orglett.7b00258

In Vitro Stepwise Reconstitution of Amino Acid Derived Vinyl Isocyanide Biosynthesis: Detection of an Elusive Intermediate

Org Lett. 2017 Mar 3;19(5):1208-1211. doi: 10.1021/acs.orglett.7b00258. Epub 2017 Feb 17.

Authors

Wei-Chen Chang¹, Dev Sanyal¹, Jhih-Liang Huang¹, Kuljira Ittiamornkul², Qin Zhu², Xinyu Liu²

Affiliations

¹ Department of Chemistry, North Carolina State University , Raleigh, North Carolina 27695, United States , and.
² Department of Chemistry, University of Pittsburgh , Pittsburgh, Pennsylvania 15260, United States.

PMID: 28212039
DOI: 10.1021/acs.orglett.7b00258

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Amino Acids
Cyanides / chemistry*
Molecular Structure

Substances

Amino Acids
Cyanides