Literature DB >> 28212039

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

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

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.

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Year:  2017        PMID： 28212039     DOI： 10.1021/acs.orglett.7b00258

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  6 in total

1.  Pathway from N-Alkylglycine to Alkylisonitrile Catalyzed by Iron(II) and 2-Oxoglutarate-Dependent Oxygenases.

Authors:  Tzu-Yu Chen; Jinfeng Chen; Yijie Tang; Jiahai Zhou; Yisong Guo; Wei-Chen Chang
Journal:  Angew Chem Int Ed Engl       Date:  2020-03-10       Impact factor: 15.336

2.  Isonitrile Formation by a Non-Heme Iron(II)-Dependent Oxidase/Decarboxylase.

Authors:  Nicholas C Harris; David A Born; Wenlong Cai; Yaobing Huang; Joelle Martin; Ryan Khalaf; Catherine L Drennan; Wenjun Zhang
Journal:  Angew Chem Int Ed Engl       Date:  2018-07-03       Impact factor: 15.336

3.  Elucidating the Reaction Pathway of Decarboxylation-Assisted Olefination Catalyzed by a Mononuclear Non-Heme Iron Enzyme.

Authors:  Cheng-Ping Yu; Yijie Tang; Lide Cha; Sergey Milikisiyants; Tatyana I Smirnova; Alex I Smirnov; Yisong Guo; Wei-Chen Chang
Journal:  J Am Chem Soc       Date:  2018-11-05       Impact factor: 15.419

4.  Biosynthesis of Sinapigladioside, an Antifungal Isothiocyanate from Burkholderia Symbionts.

Authors:  Benjamin Dose; Sarah P Niehs; Kirstin Scherlach; Sophie Shahda; Laura V Flórez; Martin Kaltenpoth; Christian Hertweck
Journal:  Chembiochem       Date:  2021-05-04       Impact factor: 3.461

5.  Elucidation of divergent desaturation pathways in the formation of vinyl isonitrile and isocyanoacrylate.

Authors:  Wantae Kim; Tzu-Yu Chen; Lide Cha; Grace Zhou; Kristi Xing; Nicholas Koenig Canty; Yan Zhang; Wei-Chen Chang
Journal:  Nat Commun       Date:  2022-09-12       Impact factor: 17.694

Review 6.  Recent advances in hapalindole-type cyanobacterial alkaloids: biosynthesis, synthesis, and biological activity.

Authors:  Robert M Hohlman; David H Sherman
Journal:  Nat Prod Rep       Date:  2021-09-23       Impact factor: 15.111
  6 in total

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