Literature DB >> 29232124

Mechanistic Studies on Tryptophan Lyase (NosL): Identification of Cyanide as a Reaction Product.

Dhananjay M Bhandari1, Dmytro Fedoseyenko1, Tadhg P Begley1.   

Abstract

Tryptophan lyase (NosL) catalyzes the formation of 3-methylindole-2-carboxylic acid and 3-methylindole from l-tryptophan. In this paper, we provide evidence supporting a formate radical intermediate and demonstrate that cyanide is a byproduct of the NosL-catalyzed reaction with l-tryptophan. These experiments require a major revision of the NosL mechanism and uncover an unanticipated connection between NosL and HydG, the radical SAM enzyme that forms cyanide and carbon monoxide from tyrosine during the biosynthesis of the metallo-cluster of the [Fe-Fe] hydrogenase.

Entities:  

Year:  2018        PMID： 29232124      PMCID： PMC6078386          DOI： 10.1021/jacs.7b09000

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  17 in total

1.  [FeFe]-hydrogenase cyanide ligands derived from S-adenosylmethionine-dependent cleavage of tyrosine.

Authors:  Rebecca C Driesener; Martin R Challand; Shawn E McGlynn; Eric M Shepard; Eric S Boyd; Joan B Broderick; John W Peters; Peter L Roach
Journal:  Angew Chem Int Ed Engl       Date:  2010-02-22       Impact factor: 15.336

2.  Aminofutalosine Synthase: Evidence for Captodative and Aryl Radical Intermediates Using β-Scission and SRN1 Trapping Reactions.

Authors:  Sumedh Joshi; Nilkamal Mahanta; Dmytro Fedoseyenko; Howard Williams; Tadhg P Begley
Journal:  J Am Chem Soc       Date:  2017-08-03       Impact factor: 15.419

Review 3.  Radical S-adenosylmethionine (SAM) enzymes in cofactor biosynthesis: a treasure trove of complex organic radical rearrangement reactions.

Authors:  Angad P Mehta; Sameh H Abdelwahed; Nilkamal Mahanta; Dmytro Fedoseyenko; Benjamin Philmus; Lisa E Cooper; Yiquan Liu; Isita Jhulki; Steven E Ealick; Tadhg P Begley
Journal:  J Biol Chem       Date:  2014-12-04       Impact factor: 5.157

4.  Reactivity of the nitrogen-centered tryptophanyl radical in the catalysis by the radical SAM enzyme NosL.

Authors:  Haocheng Qianzhu; Wenjuan Ji; Xinjian Ji; Leixia Chu; Chuchu Guo; Wei Lu; Wei Ding; Jiangtao Gao; Qi Zhang
Journal:  Chem Commun (Camb)       Date:  2016-12-22       Impact factor: 6.222

5.  Fine-tuning of a radical-based reaction by radical S-adenosyl-L-methionine tryptophan lyase.

Authors:  Giuseppe Sicoli; Jean-Marie Mouesca; Laura Zeppieri; Patricia Amara; Lydie Martin; Anne-Laure Barra; Juan C Fontecilla-Camps; Serge Gambarelli; Yvain Nicolet
Journal:  Science       Date:  2016-03-18       Impact factor: 47.728

6.  Site-specific mutagenesis of the alpha subunit of tryptophan synthase from Salmonella typhimurium. Changing arginine 179 to leucine alters the reciprocal transmission of substrate-induced conformational changes between the alpha and beta 2 subunits.

Authors:  H Kawasaki; R Bauerle; G Zon; S A Ahmed; E W Miles
Journal:  J Biol Chem       Date:  1987-08-05       Impact factor: 5.157

7.  CO and CN- syntheses by [FeFe]-hydrogenase maturase HydG are catalytically differentiated events.

Authors:  Adrien Pagnier; Lydie Martin; Laura Zeppieri; Yvain Nicolet; Juan C Fontecilla-Camps
Journal:  Proc Natl Acad Sci U S A       Date:  2015-12-22       Impact factor: 11.205

8.  A "radical dance" in thiamin biosynthesis: mechanistic analysis of the bacterial hydroxymethylpyrimidine phosphate synthase.

Authors:  Abhishek Chatterjee; Amrita B Hazra; Sameh Abdelwahed; David G Hilmey; Tadhg P Begley
Journal:  Angew Chem Int Ed Engl       Date:  2010-11-08       Impact factor: 15.336

9.  Tryptophan Lyase (NosL): Mechanistic Insights from Substrate Analogues and Mutagenesis.

Authors:  Dhananjay M Bhandari; Hui Xu; Yvain Nicolet; Juan C Fontecilla-Camps; Tadhg P Begley
Journal:  Biochemistry       Date:  2015-07-29       Impact factor: 3.162

10.  Mechanistic study of the radical SAM-dependent amine dehydrogenation reactions.

Authors:  Xinjian Ji; Wan-Qiu Liu; Shuguang Yuan; Yue Yin; Wei Ding; Qi Zhang
Journal:  Chem Commun (Camb)       Date:  2016-08-18       Impact factor: 6.222
View more
  9 in total

1.  Capturing Intermediates in the Reaction Catalyzed by NosN, a Class C Radical S-Adenosylmethionine Methylase Involved in the Biosynthesis of the Nosiheptide Side-Ring System.

Authors:  Bo Wang; Joseph W LaMattina; Savannah L Marshall; Squire J Booker
Journal:  J Am Chem Soc       Date:  2019-04-01       Impact factor: 15.419

Review 2.  Making and breaking carbon-carbon bonds in class C radical SAM methyltransferases.

Authors:  Marley A Brimberry; Liju Mathew; William Lanzilotta
Journal:  J Inorg Biochem       Date:  2021-10-22       Impact factor: 4.155

3.  Characterization of the Oxazinomycin Biosynthetic Pathway Revealing the Key Role of a Nonheme Iron-Dependent Mono-oxygenase.

Authors:  Daan Ren; Yu-Hsuan Lee; Shao-An Wang; Hung-Wen Liu
Journal:  J Am Chem Soc       Date:  2022-06-10       Impact factor: 16.383

4.  L-tyrosine-bound ThiH structure reveals C-C bond break differences within radical SAM aromatic amino acid lyases.

Authors:  Patricia Amara; Claire Saragaglia; Jean-Marie Mouesca; Lydie Martin; Yvain Nicolet
Journal:  Nat Commun       Date:  2022-04-27       Impact factor: 17.694

Review 5.  Following the electrons: peculiarities in the catalytic cycles of radical SAM enzymes.

Authors:  Mark W Ruszczycky; Aoshu Zhong; Hung-Wen Liu
Journal:  Nat Prod Rep       Date:  2018-07-18       Impact factor: 13.423

6.  An Aminoimidazole Radical Intermediate in the Anaerobic Biosynthesis of the 5,6-Dimethylbenzimidazole Ligand to Vitamin B12.

Authors:  Derek M Gagnon; Troy A Stich; Angad P Mehta; Sameh H Abdelwahed; Tadhg P Begley; R David Britt
Journal:  J Am Chem Soc       Date:  2018-09-27       Impact factor: 15.419

7.  An Obligate Peptidyl Brominase Underlies the Discovery of Highly Distributed Biosynthetic Gene Clusters in Marine Sponge Microbiomes.

Authors:  Nguyet A Nguyen; Zhenjian Lin; Ipsita Mohanty; Neha Garg; Eric W Schmidt; Vinayak Agarwal
Journal:  J Am Chem Soc       Date:  2021-07-02       Impact factor: 15.419

Review 8.  New developments in RiPP discovery, enzymology and engineering.

Authors:  Manuel Montalbán-López; Thomas A Scott; Sangeetha Ramesh; Imran R Rahman; Auke J van Heel; Jakob H Viel; Vahe Bandarian; Elke Dittmann; Olga Genilloud; Yuki Goto; María José Grande Burgos; Colin Hill; Seokhee Kim; Jesko Koehnke; John A Latham; A James Link; Beatriz Martínez; Satish K Nair; Yvain Nicolet; Sylvie Rebuffat; Hans-Georg Sahl; Dipti Sareen; Eric W Schmidt; Lutz Schmitt; Konstantin Severinov; Roderich D Süssmuth; Andrew W Truman; Huan Wang; Jing-Ke Weng; Gilles P van Wezel; Qi Zhang; Jin Zhong; Jörn Piel; Douglas A Mitchell; Oscar P Kuipers; Wilfred A van der Donk
Journal:  Nat Prod Rep       Date:  2020-09-16       Impact factor: 15.111

9.  Biosynthesis of the sactipeptide Ruminococcin C by the human microbiome: Mechanistic insights into thioether bond formation by radical SAM enzymes.

Authors:  Clémence Balty; Alain Guillot; Laura Fradale; Clémence Brewee; Benjamin Lefranc; Christian Herrero; Corine Sandström; Jérôme Leprince; Olivier Berteau; Alhosna Benjdia
Journal:  J Biol Chem       Date:  2020-09-24       Impact factor: 5.157
  9 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.